On the list of firsts in America: public park, public school, printing press, newspaper, post office, police force, subway, first full face transplant, chocolate factory, anti-public smoking law, UFO sighting, and brothel.

Boston also has the oldest restaurant, oldest baseball field, oldest college, best business school, best public schools, most expensive hotels, and apparently is the city with the worst drivers!

Needless to say, there are tons of places to visit and things to see in this exciting city!

So if it’s time to visit Boston, a City of Wonder, and experience all the fabulous things to do in Boston with kids, then read on to see the best Boston attractions for family adventures!

Is Boston Worth Visiting with Kids?

This is a city that combines the flavor of some of my most loved cities in the world.

As we wandered around certain areas I had a feeling like I was back in London, or maybe Dublin, and at times even Sydney. And then gluing together the charm of these three cities is the American spirit.

All my favorite places in the world for charm, sophistication and a little mix of fun and debauchery.

That’s why Boston Massachusetts has probably scooted in as my favorite city in the USA, and is definitely worth visiting with kids.

In Boston the people are friendly, have a great sense of humor, they have a strong sporting culture (all four pro sports teams), and seem to love fun and acceptance.

We soon learned the way they pronounce their words – skipping the pronunciation of the letter r – means they sound really Aussie!

Finally, a bartender who can understand me when I ask for a beer or where I can park my car.

Is Boston Walkable?

Boston is a small walkable city, absent of notable high rises, and is full of historical charm and beauty.

It wasn’t until walking around here and feeling so free and spacious despite all the crowds made me realize how constrictive and restrictive NYC can be.

Things to Do in Boston MA with Kids

There are many family-friendly things to do in Boston; we barely scratched the surface after our three-day trip to Boston.

We’ll definitely be back, probably more than one time. Boston was included in our best road trips in the USA list.

1. The Boston Freedom Trail Tour

The Freedom Trail Guided Walking tour is definitely one of the best things to do in Boston.

We laughed the whole way through it at our guide’s dry sense of humor and his funny way of telling the truth about the history of Boston.

There’s no better way to learn and remember history than through entertaining stories whilst you stand in front of the historic sites where the stories happened.

We only did the short tour which takes in half of the Freedom Trail.

The Freedom Trail stretches 2.5 miles from Boston Common, the oldest public park in Boston, to Bunker Hill. I’d love to do the second half that ends in Bunker Hill. Ours stopped at Faneuil Hall.

The 2.5-mile tour would be best for older kids since it requires a longer attention span (and more energy).

You can take a self-guided tour of the Freedom Trail.

But I’d recommend taking the guided tour though as you gain so much more from the stories and knowledge of the guides, who are friendly and happy to answer your questions.

2. Indulge in Italian coffee and Cannoli at Modern Pastry, North End

This was seriously the best afternoon break experience I have had in a long time.

It was the perfect elixir after a long day of driving and walking to explore the historical North End area of Boston. We immediately fell in love with its cobblestone streets and narrow alleyways.

A wander down the main street brings an aroma of the coffee, pizza, and good Italian pastries.

We stopped at Modern Pastry for our Italian coffee and cannoli.

Their pastry cabinet is filled with delicious pastries and cakes of all types, so put this on your list of things to do with kids in Boston.

You can order and go, or have table service. We chose to sit and rest for a while.

And we were thrilled they had gluten-free cannoli’s, which were delicious with a rich, black Italian coffee.

You know when you have a simple meal that you’ll remember for the rest of your life, not just for the taste, but for the moment it encapsulated.

This Italian coffee and cannoli at Modern Pastry in the North End is that for me!

Younger kids, older kids, teens and grandparents will all love this!

3. Marvel at the Old North Church, North End

As we wandered past the Paul Revere Statue, stopping to pay our tributes to the man who helped save America from being captured by the British, we stumbled upon a church that had a flow of people wandering inside.

Well, just another church I thought. You tend to get blasé about them.

But I could see Mum was interested so didn’t want to completely dismiss it. She had a peek in and decided it looked interesting enough to pay the suggested donation and have a look.

I loved it.

It was unlike any church I have ever been in and upon entering we discovered its interesting American history story.

Founded in 1723, the Old North Church is the oldest standing church in the City of Boston, made famous by Paul Revere’s midnight ride and, “One if by land, two if by sea.”

On the evening of April 18, 1775, when the church sexton, Robert Newman, and Vestryman Capt. John Pulling, Jr. climbed the steeple and held high two lanterns as a signal from Paul Revere that the British were marching to Lexington and Concord by sea across the Charles River and not by land.

The American Revolution began.

The church is filled with white private cabined pews and is unlike any other church I have seen.

Various pews have names and numbers on them which tell the story of different people who worshiped in the church.

It also tells the true story of the Midnight Ride and how it was altered by Longfellow’s’ famous poem.

Don’t you just love unexpected surprises like this when you travel?

With our style of travel now in researching and planning and receiving tips from so many people around the world, we tend to not have so many of these surprises anymore.

It thrills me when we do, even if it does happen to come from a building with a steeple.

4. Visit Paul Revere’s House, North End

Looking for even more things to do in North End Boston?

Paul Revere’s house is still standing, it is the oldest house in Boston and one of the most popular Boston attractions.

It’s located in the North End and can be visited on a short tour.

We decided just to look at it from the outside. After hearing more of the story over the next couple of days, I wished we had visited.

We’ll make it one of our top things to do in Boston next time we visit.

5. Eat at America’s oldest restaurant, The Union Oyster House

A Bostonian local, who is a Raleigh friend of ours, basically said we’ll be doing ourselves a great disservice if we don’t eat at the Union Oyster House.

I was concerned it might be one of those kitschy tourist traps, but it wasn’t at all.

It has a story behind it that makes it interesting.

The Union Oyster House is the oldest restaurant in Boston and the oldest restaurant in continuous service in the U.S. — the doors have always been open to diners since 1826.

And it possibly has had the most presidential customers.

Jimmy Carter, Bill Clinton, George Bush Snr, and Obama apparently came in for a takeaway chowder. John F Kennedy was a frequent visitor, and even has his favorite booth dedicated to him.

A future king of France, Louis Philippe, lived on the second floor. Exiled from his country, he earned his living by teaching French to many of Boston’s fashionable young ladies.

Printer Isaiah Thomas published his newspaper “The Massachusetts Spy,” long known as the oldest newspaper in the United States, from the upper floor of the building in 117.

Federal troops received their “war wages” in the official pay-station, which was right where we sat for lunch.

It’s possible Washington himself sat there!

And, the toothpick was first used in the United States at the Union Oyster House.

Never mind the delicious food, the fascinating history is enough to want to dine here.

Pull up a seat at the famous semi-circular oyster bar and enjoy a plate of freshly shucked oysters.

It’s in the most charming section of Boston, which is a triangle section of cobblestone streets and historic buildings, including the Bell in Hand Tavern across from it.

Be sure to try the traditional Boston dishes such as Lobster Rolls and Clam Chowder here.

6. Relax at Boston Common

How beautiful are Boston Commons and the Boston Public Gardens which continue this sprawling urban green space?

In 1634, Boston Common was created as America’s first public park, making it the oldest public park in the USA.

The 44 acres of Boston Commons were sold by the first settler of the area, William Blackstone for 30 pounds to the Puritan Colonists on the condition that it would always remain a free public space.

A promise still kept today.

No ticketed events are allowed here and it’s open to the public to wander, picnic, and take a break from the hectic Boston pace.

Although, I don’t feel it’s too hectic, to be honest. Even the squirrels love it here.

The common land was used to graze local livestock until 1830. It was also a site for Puritanical punishments, home to a whipping post and stocks.

Pirates, murderers, and witches were hanged from the tree known as “The Great Elm,” now gone

We visited during Memorial weekend and saw the touching Memorial Day Flag Garden where more than 37,000 flags are planted, each honoring a fallen hero from Massachusetts in wars from the American Revolution until today.

A must-see in Boston on Memorial day. 

But way too many flags. Let’s work for peace please!

Boston Common is the site of wide open green spaces and includes a bandstand, a carousel, a frog pond wading pool and playground, and tennis courts, as well as the site of many fairs & festivals. 

7. Drink at America’s oldest tavern, The Bell in Hand Tavern

As we walked out of the Union Oyster I glanced to the right and briefly saw a sign at the pub diagonally across saying something about the oldest tavern in America.

I filed it away for another time.

And when that time came after watching a Red Sox baseball game at Fenway Park when Mum and Dad took the girls and insisted Craig and I take a break and have a night on our own, The Bell in Hand Tavern sprang into my head.

I’m so glad we did.

It had an English charm about it and made me miss my years of living in London.

Our bar lady was super friendly, we chatted away with a couple visiting from Texas, AND it had the best cider I have ever had (more on that below) perfect for a hot summer’s night.

The buffalo chicken nachos were pretty good too.

In the back room, they have live music. It was a little cramped and loud so we were happy to chill at the bar – kind of what happens when you get older.

The Bell in Hand Tavern is the longest continuously operating tavern in the United States, having been built in 1795 by Boston’s retired Town Crier.

The Town Crier’s job was to shout the big news and special events across town, and boy did the original proprietor of the Bell in Hand shout about some pretty famous news:

• the Boston Tea Party
• the Declaration of Independence
• the impending Battle of Bunker Hill
• and of course, the defeat of the British

The Bell In Hand Tavern has always been known as a place where anyone is welcome, and everyone comes to drink, eat and enjoy lively conversations.

It’s exactly what we experienced.

Consider this for your list of things to do in Boston at night, or during the day.

8. Smell the Roses at the Boston Public Gardens

Looking for more free things to do in Boston with kids?

Across from the Boston Commons is the Boston Public Garden.

As the name suggests, it is probably a little more colorful and prettier than the Boston Commons with its lake, swan boat rides, and pretty gardens.

This is also where you will find the George Washington Monument, one of the most photographed places in Boston.

Boston Public Garden, established in 1837, was the first public botanical garden in America.

Whereas the Boston Common was practical and pastoral and built for crosstown travel, the public garden was decorative and flowery and made for strolling along meandering pathways.

Walking with your family makes this a very kid-friendly park and a place to spend time together.

9. Shop and Eat at Faneuil Hall Marketplace and Quincy Market

Faneuil Hall Marketplace is another one of the downtown Boston historic sites in the center of the historical area in downtown and is a fabulous meeting point.

It also has a lot of history.

Surrounding it are various markets and, like most tourist areas, it’s here where you’ll find a lot of street performers and overpriced shopping and food.

We actually didn’t find it too bad, and I picked up a beautiful handbag from a Turkish store.

Looking for places to eat in Boston? The Quincy Market has loads of food stalls for you to choose from.

We were very happy as within Quincy Market we found gluten-free Boston Chowder. Now that is difficult to find and we finally were able to sample one of Boston’s most famous dishes.

There are also a few ice cream shops and boutiques inside too.

10. (Window) Shop on Newbury Street

I think it took my Mum and me a while to speak after we started walking down Newbury Street.

Each of us silently took in how beautiful it was.

Until finally, I think it was Mum who breathed and said, “Wow. It is just so beautiful. Look at those buildings.”

It’s not like any other high-end shopping street you have walked along before.

I’ve been to some of the most well-known, Rodeo Drive in Beverly Hills, 5th Avenue New York, Magnificent Mile in Chicago, I love all of them, but Newbury Street is something special.

Inside rows of terraced houses are not families going about their day but boutique dress stores, jewelry stores, cafes, and restaurants.

Once again, I recognize the space due to a lack of high rises. It’s colorful and gentle moving.

I was so glad we decided to walk from Boston Gardens and along Newbury Street to Fenway Park for our Red Sox baseball game.

It took us longer than 30 minutes as we stopped to look at stores, take in the views of historical and magnificent churches, and drop in for a coffee in the sunken front courtyard of  Barrington Coffee Roasters.

Coffees here are good peeps. Having the name roastery in a café name is often a good sign it will be.

11. Watch a Boston Red Sox Game at Fenway Park

Take me out to the Ball Game!

Going to baseball games as a family is one of the best activities for kids in Boston and adults alike.

Not only do you get this iconic baseball song in the oldest baseball stadium in America, you also experience a very unique sing-a-long.

It made me fall in love with baseball and the Red Sox because of their acknowledgment and honoring of my soul.

Yes, at the bottom of the eighth innings, the stadium and the crowd breaks into the most truthful song in the world, Sweet Caroline!!

My parents were stoked that they sang that song especially for me, lol.

We had a great time watching the Red Sox beat Atlanta at Fenway Park.

It truly is one of the most iconic places to watch baseball in the US and one of the cool things to do in Boston MA. Don’t miss it!

These are the cultural experiences we travel for.

Fenway Park is a small baseball field and its legendary for its green monster, which is basically a giant green fence that the baseball players love to hit home runs over.

We saw a couple happen during the game.

You couldn’t have a bad seat in the house. We sat just behind the left field and had perfect views. It’s a really fun event and one of the most iconic places to go in Boston!

We recommend checking out the following fan-favorite bars around the stadium before (get there early) or after the game:

• Cask ‘N Flagon
• Game On
• The Lansdowne Pub
• Tony C’s Sports Bar & Grill
• >Boston Beer Works
• and the classic Bleacher Bar

12. See an Overview of Boston on The Boston Duck Tour

Looking for fun things to do in Boston with kids? Do this. 

We’ve been on a few duck tours and always enjoy them, but the Boston Duck Tour has been the best one yet.

There’s just something about this city, even their amphibious vehicles rock.

Our guide Betty, was hilarious.

I enjoyed her passion for the city and her stories were entertaining, informative and insightful. And her jokes weren’t too cheesy like some duck tour guides can do.

The tour goes for 80 minutes and drives around to the most important and historical Boston tourist attractions and neighborhoods.

The tour includes 20 minutes of cruising down the Charles River with views of Boston and Cambridge skylines.

Savannah welcomed the opportunity to be the Captain of the boat and steer it for little. Tell your child to not be shy in volunteering.

We got off the Duck with a much longer list of things to do in Boston after discovering one or two more places we wanted to go back and explore more.

These kind of city overview tours are so great to do at the beginning of your trip, not just for the stories and historical insights, but also to discover places of interest.

We certainly had a time constraint in doing so but we managed to rearrange a few things to fit in a few more attractions.

13. Get Educated on A Harvard Walking Tour

Boston is home to Harvard University, so while you are here you have to take a stroll.

Even though when we joined the Harvard walking tour led by students we could not access Harvard Yard – the drawcard of the experience – due to a private event, I absolutely loved the Hahvahd Walking Tour.

And I would do it again even if it meant still missing the Yard.

It was awesome to gain insight into life in one of the most prestigious colleges in the world.

From our guide Tim we learned the history of Harvard, the culture of Harvard, and what incredibly inspiring, well-rounded individuals it helps produce.

I love their style and philosophy and I am sure no matter what you graduated with, a degree from Harvard would open up many doors just because of the education and how it raised fine young adults.

I’d be delighted if my girls went to Harvard. It has certainty gone them thinking about college.

You know something is good if you buy an item of clothing as a souvenir. My Mum went straight to the gift shop to buy herself a gorgeous sweater. She also bought one for me.

Perhaps she feels it’s not too late for her daughter to go to Harvard? Or maybe even herself.

It’s never too late Mum. As long as I can come to visit you!

14. Wander the historical neighborhood of Beacon Hill

Back Bay is the oldest neighborhood in Boston and is situated on the Boston Common.

You know it’s part of the original Boston as it’s hilly. Any flat piece of land in Boston is a landfill. It was once much smaller than it is.

Back Bay is where you’ll find cobblestone streets and residential terraced homes. Duck down some of these streets and you’ll find serenity – it’s surprising the lack of cars and people wandering around.

Head out onto the main street, however, Charles St, and you’ll find boutique stores, cafes, restaurants and plenty of people.

15. Find your Alibi at the Liberty Hotel

One of the most unique places in Boston to visit.

On our Duck tour, we learned about the Liberty Hotel, which used to be a former prison, Charles Street Jail, a national historic landmark and architectural gem built in 1851.

As we were wandering around Beacon Hill we decided to pop in and have a look. It’s worth it.

It’s certainly not what you’d expect a prison to look like. It has now been imaginatively restored into a five-star hotel complete with a restaurant, The Clink.

The Catwalk is a hotel-guest-only retreat that is on the original Charles Street Jail catwalk, and the former exercise yard, which is now a private, beautifully landscaped courtyard.

Don’t miss the Alibi bar, set in the old “drunk tank” for a drink either inside the brick cell walls or the outside patio.

Look at the posters on the walls of celebrities who have been arrested and what their alibis were. It’s hilarious and will be one of the things to do in Boston you’ll be telling people about when you get home.

We’d love to stay at the Liberty Hotel in Boston on our next visit. As it’s a luxury five-star hotel, the girls are demanding it!

16. Have a drink at the Cheers Bar

There is no real Cheers bar in Boston, however, there is the pub that inspired the massively popular TV show.

The Bull & Finch Pub as it was previously known was founded in 1969 in Beacon Hill and became the inspiration for the setting of the Cheers bar, as it was in an area that was famous for colorful pubs, sports teams and lively politics.

The exact recipe you need for interesting pub conversation right?

The

It’s a great neighborhood bar, albeit now a little bigger, and is across the road from the Boston Public Gardens.

Pull up a seat at the bar if you can find one, or a seat at the window for views over your pint – one of those “touristy” places to visit in Boston.

17. Visit Downeast Cider House

Okay, so we didn’t visit the Downeast Cider House, but I am recommending it as one of the best things to do in Boston, especially if you are gluten-free and love cider.

Downeast Cider is the best cider I have ever tasted.

It’s a local Boston craft cider house founded by some college friends in 2011.

We had a pint of it first at the Cheers Bar, and then several at the Bell in Hand Tavern.

It was quite citrusy in flavor and the closest to my favorite wheat-style beer that I can no longer drink. I’m currently trying to remember which cider it was so I can order some cases to be sent to me in Raleigh.

It’s that good!

Another couple of things I loved after checking out their website. They are committed to taking no shortcuts by using only fresh-pressed juices and natural ingredients.

No wonder it was so bloody good.

And, on their website, they let you know they pay their employees well so no need to tip. I am on the hunt for more places like this in America to recommend to you!

The Cider House is located in East Boston and they do tours of the cider house with complimentary samples and flights of cider.

Look out for their ciders in the Boston bars as well.

18. Watch the Celtics and the Bruins at TD Garden

Boston is a sport city and home to some of the best basketball teams in the country. The TD Gardens is a legendary venue for watching NBL, especially the Bruins and Celtics who were on the verge of leaving Boston, until The Boston Garden, now known as TD Gardens, was revamped in the early 90s.

Today you can still watch the Bruins and celtics play at the arena, as well as catch live music concerts and comedy gigs.

If you’re looking for things to do in Boston with kids at night, then be sure to check out the events calendar to see what’s happening.

19. See the Mapparium at the Mary Baker Eddy Library

The Mapparium is an enormous three-story stained glass globe located inside the Mary Baker Eddy Library. This marvelous structure was created in the early 1930s by local architect Chester Lindsay Churchill.

He was commissioned to design the new Christian Science Publishing Society HQ who wanted a gigantic structure to remember them by.

Mapparium offers a unique perspective of the map of the world. When you look at countries on a paper map, everything feels so small and far away. The Mapparium makes you realize the Earth is huge, but so small at the same time.

This is certainly an unmissable thing to see in Boston with kids.

20. Check Out Castle Island

Castle Island is somewhat of a hidden gem in Boston. The island was constructed as a new fort in 1801 by the war department, which defended Boston from the British in an attack in 1812.

The island is an area of historical importance. It’s also where you’ll find a monument to Donald McKay, the maker behind the clipper ships Flying Cloud and Sovereign of the Seas.

Today people visit Castle Island not so much for the history but for the beaches. There is also a lovely pier where you can go fishing, and kids will enjoy playing in the huge playground.

21. Admire the Architecture of Massachusetts State House

Boston is not short of stunning buildings to marvel at, but one that should definitely be stopped and admired is the Massachusetts State House.

This old state house is the state capitol building and where you’ll find the Massachusetts General Court and the offices of the Governor of Massachusetts.

It was built in 1798 and designed by Charles Bulfinch, but has been enlarged several times since. It’s known for being one of the oldest state capitols still in use today.

It was declared a National Historic Landmark for its architectural significance in 2015.

22. Walk Along the Charles River Esplanade

If you’re looking for something relaxing to pass the time, you can’t go wrong with a nice stroll along the esplanade. The Charles River Esplanade is a three-mile walkway that meanders along the river.

It passes several top attractions in Boston such as the Museum of Science and the Boston University Bridge.

If you’re visiting Boston in Autumn, this is a great place to check out. The colors of the trees are washed in oranges and yellows, which are reflected in the water of the river. Such a beautiful sight!

23. Learn About Maritime History at Charlestown Navy Yard

The Charleston Navy yard is a former shipping yard that was in operation for more than 170 years. Today the yard is home to a crane, Building 10, Building 5, and the Marine Barracks.

Visitors can explore the navy yard which has been preserved in its original historic state.

Your children may enjoy a free tour of the Old Ironsides and the USS Constitution Museum in Charlestown – the oldest commissioned warship afloat in the world.

If you’re interested in maritime history, you may also want to check out the Boston Tea Party Ships & Museum in South Boston.

Other Things to Do in Boston with Kids

We tend to travel to experience what is unique to a destination. We find most children’s museums, playgrounds, and other generic museums to be pretty much the same no matter what city you are in.

So we invest our time and money into those attractions and activities that tell the Boston story. Our kids always have a great time.

Here are a few other Boston attractions we either did not have time for or decided it was too generic.

• The Old Town Trolley tour provides entertaining commentary as you it takes visitors to Boston attractions like Paul Revere’s House, the Old North Church, the Old South Meeting House, Faneuil Hall, the Bunker Hill Monument, the Boston Massacre Site, the Gaslamp Quarter and 90 more really iconic Boston places. 
• For those with a longer time in Boston, you may want to consider a day trip to the Boston Harbor Islands. There are 34 islands with their own attractions such as the historic Fort Warren and tours of America’s oldest lighthouse.
• It’s popular for visitors to take a Boston Whale Watching tour. We’ve done so many of them that we chose to do the more unique Boston experiences instead.
• The Boston Museum of Science has interactive exhibits that younger kids will love.
• the LEGOLAND Discovery Center has several Boston landmarks recreated in Lego bricks in Miniland, rides, a $D cinema, and a play area.
• The Franklin Park Zoo is a 72-acre zoo located in Boston, Massachusetts. Again, like a typical zoo you’ll find lions, tigers, giraffes, and zebras, along with gorillas, tropical birds, butterflies and farm animals
• New England Aquarium has more than 8,000 aquatic animals including the playful penguin pool with three different species of more than 80 penguins. Don’t miss feeding time at the Giant Ocean Tank, home to a plethora of marine creatures such as sharks and loggerhead sea turtles.

Where to Stay in Boston

It was challenging to find accommodation in Boston that wasn’t hugely expensive.

Boston is said to have the most expensive accommodation in the country! There go those superlatives again.

And we visited over Memorial Weekend, one of the busiest weekends in the year.

Airbnb was not giving me anything too inspiring.

Then I remembered that Booking.com have apartment rentals and I found a great deal on a brand new apartment in the South End, not far from the Seaport District.

The South Boston Family Getaway at West Square Apartments was about a 40 minute walk into the city or a quick and relatively cheap Lyft ride downtown or anywhere really.

You can see more like it at the Sonder Seaport District. It seems the particular apartment we stayed in is no longer available but this one is in the same area and very similar.

We loved the apartment.

It was spacious and comfortable and so modern with beautiful décor. There were two bedrooms and a sofa bed.

One of the beds was a King so we could throw one parent in the King with the girls and the other on the sofa bed.

We like to do it that way so the girls can go into the room and sleep while us oldies relax with a bit of TV.

We got a little hooked on the Netflix show Turn while on our road trip, which is all about patriot spies during the War of Independence.

Perfect to watch when you’re in a city like Boston!

Final Thoughts on Things to Do in Boston with Kids

I’ve just loved reliving our time in Boston writing this post. It’s a unique and fun city and I understand why so many people rave about Boston.

I am sure there are many more must not miss things to do in Boston. Sadly our time was too short to do them all.

Please let us know in the comments what your favorite things to do in Boston are so we won’t miss them on our next visit.

More Tips for New England

Visiting other parts of New England? Then you might find these resources useful.

• 7 Helpful Tips for a New England Road Trip in the Fall
• 10 Beautiful Places to Visit in Vermont, New England
• 8 Things to do in Martha’s Vineyard with kids! (Relaxing beach retreat)
• Things to do in Manchester VT for a Relaxing and Fun Fall Road Trip

Boston Travel Video

Check out the fun we had in Boston.

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Most people only think of autumn road trips, but New England can be great any time of year and can even be romantic.

These are some small towns you can’t miss!

1. Plymouth, Massachusetts

Plymouth rock, not worth it. It’s a rock with “1620” carved into it from when the pilgrims first came to the coast.

What is worth it? Plimouth Plantation where you can interact with actors dressed as the pilgrims and the Wampanoag tribe and it’s kid friendly.

Perfect for historians and a great getaway from Boston.

2. Burlington, Vermont

One of the best New England vacation spots since Burlington isn’t really near any major highway systems like I-95 so it’s a perfect off the beaten track New England road trip in fall!

From their waterfront park where you can enjoy Lake Champlain weird things like the world’s tallest filing cabinet, this small town has tons to enjoy.

3. Bar Harbor, Maine

If you really want a full weekend getaway in New England, you have to see this small island.

From Acadia National Park that’s right there, full of hikes and viewpoints in Maine to historic Bar Harbor.

There are carriage rides to enjoy at all times of the year too, and learn things you never knew about the Rockefellers!

4. Merrimack, New Hampshire

Romantic getaways in New England have to include this small town, simply because of all of the breweries (both beer and wine) in the area.

Seeing the leaves change colors with fall is great along the several trails you can hike and different town parks you can visit.

5. Camden, Maine

One of the not-so-famous New England vacation spots is Camden Hills State Park.

On top of Mount Battie you can see Camden and all of Penobscot Bay. The small town itself has harbor cruises and whale watches during the appropriate times of the year, including the Snow Bowl ski resort in winter.

6. Chatham, Massachusetts

This cute beach town on the south east corner of Cape Cod can’t be missed during your New England day trip.

From pristine beaches to beautiful and historical lighthouses with amazing views it’s the place to be.

If you’re into railroads, don’t forget to visit the Chatham railroad museum.

7. Greenwich, Connecticut

From boating in Long Island sound and seeing old colonial style homes mixed in with modern mansions, Greenwich has it all.

An hour from New York makes it a great place to start your New England getaway. A famous New England attraction is Great Captain Island, which is a quick ferry ride away.

8. Jamestown, Rhode Island

With lighthouses, beaches, and forts this small island has it all.

Don’t miss Fort Adams State Park, 25 minutes away over the river in Newport, where there’s swimming, sailing, and festivals to enjoy at different times of the year.

Also, visit Castle Hill Lighthouse, which is technically on Newport Island, which is right next to Jamestown.

9. Rutland, Vermont

From hikes to children’s museums to 19th century castles, what more could you want from this beautiful New England small town?

This makes it for the perfect family destination for a New England road trip.

If you’re a fan of Norman Rockwell, visit his museum while you’re there too.

10. Groton, Connecticut

One of the best New England attractions has to be the fact that the navy has submarines in Groton.

All things aquatic are to be seen here, from their aquarium to their submarine museum and an old whaling ship now out of commission for you to enjoy during your New England trip.

More Tips for New England:

• 17 things to do in Boston
• 7 tips for a New England road trip in the fall
• 6 beautiful places to visit in Vermont
• 25 New England Romantic Getaways 

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My role is more to open up doors of possibility and help them uncover for themselves which is the right door for them to eventually walk through.

It’s why I love to travel with them, and why I continue to do so despite it being so hard. I often think of quitting and putting them back into school, so badly do I need a break and some sort of separation and individuality.

But then we get these results from the standardized homeschooling tests.

And then I think about the box I’d be putting them back into and how much they’d lose from not traveling and experiencing these many different doors of possibility.

Travel shows them all the different paths that are available to them. You only know what you know right? Travel helps them to uncover who they truly are.

Harvard University is one of the most prestigious colleges in the world. Of course you have heard of it.

On our recent trip to Boston, I did not want to leave without seeing it for myself and imagining what life as a student in Harvard would be like.

I also wanted the girls to gain an insight into Harvard University Campus life so they could begin to think about their future.

Is a college degree something they are interested in? Can they see themselves living the life of a college student?

Lead them to the learning

How can I help them see what is possible through that door and path, without me telling them about it?

It’s amazing how much children will learn and gravitate towards things when they hear it, or experience it, from people other than their parents.

If I want my girls to learn something in particular to help them grow into extraordinary young women, I often give them a book about it, or send them to  rock climbing camps, to help them learn it from themselves.

Again, opening the door and letting them walk through it.

Harvard University Tours – The HahVahd Tour with Harvard Students

We joined a walking tour of Harvard with Trademark Tours in Boston on the last morning of our Dallas to Boston road trip.

The 70 minute Harvard University tours, or HahVahd tours, are guided by Harvard University students.

Our guide, Tim graduated with a history concentration (major) just a few days before taking our tour.

Highlights:

• Harvard University History – including the untold stories and lore
• Harvard Culture – stories and tips from current students about what it’s like to live and study at Harvard
• Famous Harvardians – learn about the most famous people to attend Harvard

When a young boy asked why it was spelt Hahvahd on his shirt he switched to a Bostonian accent to show how Bostonian people don’t pronounce their ‘r’s giving a few examples, which sounded exactly like an Australian accent!

No wonder I kept thinking I was hearing a few Aussies in Boston!

Sadly for us, we could not visit Harvard Yard due to Graduation ceremonies, which is the main area of Harvard University campus and where the freshman students live and where they take their classes.

It’s also the place where the statue of John Harvard is and where the infamous Midnight scream and naked streak around the Yard happens on the night before their finals to help the students let off steam!!

Tim did an excellent job of helping us overcome this disappointment by painting a great picture of life inside the Yard and taking us to as many places as he could around Harvard.

At the end of our Harvard campus tour, the girls had a gleam in their eye as they spoke about Harvard and college and Harvard University tuition costs.

I could see they recognized the possibility and saw themselves in it.

Harvard was an experience that excited them. I was so grateful to Tim our guide for painting a picture of what Harvard was like as a student.

He told us about the history of Harvard, some famous Harvardians and some interesting stories about Harvard culture and rites of passage.

We learned how difficult it is to be accepted into Harvard and how important it is to show academic commitment and good grades, even if you do have an athletic ability, your grades are equally as important.

While I understand getting accepted into the right university here in the USA creates high pressure and stressful situation for high school students, I do like how it helps young teenagers to think about their future from an early age and make responsible choices to avoid getting into trouble and getting bad grades.

They understand early on there can be a a high price to pay if they goof off and miss out on opportunities as a result and destroy their future.

As college is not such a rite of passage for Australians, I don’t think we have such a consequence connection at such a young age, nor a deep commitment and passion for our future.

More importantly, he shared about the transformative experience of Harvard and how it trains you for life,  opens so many future doors of possibilities and helps you walk out as a much better person.

Educated, confident, introspective, and so open to life and opportunities.

Tim had a very grounded energy and a confident belief about himself and his future.

I got the impression Harvard was largely responsible for this and it made me happy to see the kind of adults it was helping to bring into the world, who will hopefully use that education to make it a better place for all.

Holding people to a higher standard is essential for creating exceptional humans and societies.

That’s what I wanted my girls to see.

Tim had an opportunity to go to Harvard because of football. He was invited to play on the team and took advantage of that opportunity to get an education at one of the best colleges in the world.

An education that has now helped him to pursue a talent and interest in the music recording world in Los Angeles.

It was something he never even knew he wanted to do until his final year.

I loved how my girls heard this story and I hope were able to discover a few clues about life. It has many twists and turns and new doors to discover.

You don’t have to know all the answers or even which path you want to walk down, but the key is to show up, take adventure of opportunities (or so called luck), work hard, have fun and be passionate, and be a decent person.

The world really is your oyster.

I think college life in America would be something the girls would love.

As Tim said, he’s not really doing anything with his degree that concentrated (majored) in history. But, it was an education and training that has helped prepare him for life and whatever career path he will follow.

I can see how valuable it is and just having “Harvard Graduate” attached to your name can bring many opportunities as it’s well recognized as a college that creates exceptional, well rounded, and educated people.

Whether they do or not, they are talking about it and considering it.

Weighing up the pros and cons of a Harvard college verse UNC, and talking with us about what you have to do to get into college, deciding which friend they’d choose to live in the college houses with.

I think Kalyra loved how Hogwarts like it sounded.

Savannah flat out said,

I want to go to Harvard. Can you get me in?

Well, Harvard offers no scholarships so we better come up with a really good investment savings plan!!

Boston Travel Video

Helpful Links for Harvard University Tours:

• Buy your Harvard “Hahvahad” walking tours here.
• Get your Boston Go Card here
• Boston Duck Tours (also included on the Premium Boston Go Card
• Find your Boston accommodation here. (We stayed at this lovely modern apartment in South Boston, which we booked through Booking.com)

Helpful posts for Massachusetts Travel

• 17 things to do in Boston with kids
• The hilarious and informative Boston Freedom Trail walking tours
• A 3 day trip to Martha’s Vineyard

I don’t think there was a movie that negatively affected me more than Jaws. So much so that when Kalyra asked to watch it last summer on a camping trip to Kerr Lake in North Carolina with friends, I vehemently said,

“No. That is not a good idea. Trust me, it will ruin your enjoyment of the beach for the rest of your life.”

Well she didn’t listen to me and watched it and thought it was the lamest movie ever (insert eye roll).

“How could you let that scare you Mum? It was so fake.”

“Back in our days love, when we had no high tech special effects in movies, that was as real as the snake crawling past your tent right now.”

I’m pretty sure the next day when we went tubing on the lake, she asked if there were sharks in the lake. Jaws made you afraid to swim anywhere you couldn’t see the bottom.

Martha’s Vineyard Massachusetts (MVY) is the fictional place of Amity, which Jaws terrorized back in 1975.

Martha’s Vineyard, more specifically the town of Edgartown, was taken over by Spielberg and his cast and crew to film what turned out to be the epic Black Panther style blockbuster of its time.

It was a summer smash hit that ruined me for life.

Where is Martha’s Vineyard?

Martha’s Vineyard Island is located approximately seven miles off the southern coast of Cape Cod in Massachusetts on the East Coast of the United States.

To get to Martha’s Vineyard, you catch a ferry from Woods Hole (near Falmouth) on Cape Cod to either Oaks Bluff or Vineyard Haven.

How to Get to Martha’s Vineyard

The Woods Hole ferry to Martha’s Vineyard takes approximately 45 minutes.

If you’re taking your car over on the Martha’s Vineyard ferry it is best to reserve your ticket in advance so you don’t miss out.

Woods Hole is about a two hour drive south of Boston and and NYC to Martha’s Vineyard takes approximately 5.5 hrs. (check traffic as this can drastically change in the North East).

Check here for ferry times and prices as it varies depending on vehicles and passengers.

Martha’s Vineyard is a Coastal Retreat for Families

We didn’t visit Martha’s Vineyard with kids to scout out Jaws filming locations.

We visited as it’s a place I’ve heard my parents mention many times growing up, most notably for its connection to the Kennedy family.

My parents, and my Aunty, are huge Kennedy fans and have followed their family’s story and lives for as long as I can remember.

It’s not just the Kennedy’s who have lived or spent time on the island. Celebrities frequently visit and can often be seen in the summer months.

Obama and his family rented a farm here one year at Chilmark for their family vacation.

As Martha’s Vineyard seems to be a coastal retreat for the wealthy, we thought we’d be in for a major treat.

I mean, when you have all that money and opportunity and you choose Martha’s Vineyard, it has to be something special.

I’d have to say I was a little disappointed with Martha’s Vineyard.

We all felt a little flat over it, although my Mum put Edgartown as one of the highlights of our Dallas to Boston road trip.

I think going to Martha’s Vineyard fell flat for us simply because we are from Australia and have been fortunate to have the opportunity to experience hundreds of beaches and islands (Australia is surrounded by 10,000+ beaches!)

Sadly, one downfall of living a nomadic life for as long as we have, is that you do experience so much, and it’s very difficult to not let that comparison creep in and dull a new experience.

I am very aware this is a problem, especially when it comes to beaches.

So while I know you trust our opinion, and that’s why I tell it to you straight, also be mindful of where our opinion comes from.

When you visit Martha’s Vineyard it may be a completely different experience for you and I don’t want to taint that because of my somewhat jaded eyes.

However, although we weren’t wowed, we did have a good time on Martha’s Vineyard with our family.

I think its important to make the most of every travel opportunity and love it for what it presents to you, even if it does fall below your expectations.

How did it fall down for us? OR how did we get it wrong?

I didn’t think the Martha’s Vineyard beaches were all that spectacular.

The weather wasn’t warm enough for swimming, although we visited Martha’s Vineyard in May, for some of you it may have been okay. I don’t usually go swimming unless it’s baking hot and the water temperature warmish.

But looking at our photos you might think otherwise.

I had done my research on things to do in Martha’s Vineyard and a couple of “oh my god so spectacular scenic drives” came up.

I was super excited to take them only to be left with a “Wait, was that it?”

Maybe if I was like my Mum who doesn’t like to do much research and just likes to show up and be surprised, I may have been more wowed.

But my expectations were placed too high.

Mostly though, I don’t think we experienced Martha’s Vineyard in the right way.

We were more on a sightseeing trip with my parents. So we wanted to move around and see notable places and experience cool local things.

I think a Martha’s Vineyard vacation is more of a rent a cottage and chill out on the beach for a week or two kind of place, which we weren’t in the right mode for. Rent a bike and cruise around the island on the many bike paths – that’s your kind of Martha’s Vineyard bucket list vacation.

Because we were a little before peak season, some cool places like the popular Chilmark Chocolates, whose owners employ young people with a range of disabilities to make and sell their candies weren’t open yet.

I can see how lingering at places like that would enhance your Martha’s Vineyard vacation.

A positive for visiting Martha’s Vineyard the week before memorial weekend did mean the crowds hadn’t entered the island yet, so it was peaceful.

We can’t imagine what it must be like on Martha’s Vineyard during the peak summer season. The crowds and the traffic is meant to be intense. Many people visit on day trips which is possible. I think to fully appreciate it’s beauty it’s best to stay on Martha’s Vineyard for at least two to three days.

I’ve seen pictures of the ferry and it was busier than the hundreds of people lining up to visit the Statue of Liberty in New York each day.

Martha’s Vineyard Things to do and see!

1. Find Serenity and Mystery on Chappaquiddick Island

Visiting Chappaquiddick Island was one of our favorite things to do in Martha’s Vineyard.

There is a 3-car-3-minute “Chappy Ferry” ride over to the island, which has maintained the Vineyard’s old world charm.

There is a spectacular 2 3/4 mile walk along a sand spit from South Beach over to Chappaquiddick Island if you want a more adventurous way to explore for the day.

Chappaquiddick is much wilder than the main island and a peaceful retreat to what you’ll find in Oaks Bluff and Edgartown.

There are no stores or restaurants on the island, so be sure to pack everything you need for the day.

Chappaquiddick is most known for the tragic Kennedy accident back in 1969.

Senator Ted Kennedy was driving a young woman named Mary Jo Kopechne home when he drove of the side of the Dike Bridge. He attempted to rescue her but she drowned and he didn’t report the accident until the next day.

It gave us a great story to discuss later on.

We stood at the spot where the accident happened and could see how in the dark of night you could be disorientated and come off it, especially if driving too fast. (They have barriers on either side of the bridge now though).

There are plenty of beaches and hiking trails to enjoy on Chappaquiddick with kids.

I would have loved to have ridden a bike over from the mainland to explore it that way. It’s small enough that you could.

There is also a 14-acre Japanese garden, Mytoi and the Cape Poge Wildlife Refuge, the nesting area for a variety of New England shorebirds.

The beach here was pretty wild but pretty, and after reading the Great White Shark warning sign on the boardwalk down to the beach, we decided swimming would not be an option for us here.

Although we have swum with sea lions before in the Port Lincoln area of South Australia, a region notorious for Great White Sharks!

We finally had confirmation that Jaws actually does exist on Martha’s Vineyard.

It has to do with the increase of seals in the area. And yes they have been seen eating them. This was an official sign, not a scare mongering tactic.

The Chappy Ferry costs:

• Passenger — $4.00 round-trip
• Car and driver — $12.00 round-trip
• Bike and rider — $6.00 round trip

Chappaquiddick Island was a top Martha’s Vineyard attraction for our family.

2. Roam around Edgartown

Edgartown is Martha’s Vineyard’s oldest and most stylish town with tidy streets that has preserved a lot of its elegant and wealthy whaling past.

You’ll see an abundance of stately white Greek Revival houses Captain’s homes lining the streets with well manicured gardens and lawns, and shady oak trees.

Many have plaques signifying which Captain owned the house.

And many of the whaling Captain’s homes have been converted into inns, restaurants and one-of-a-kind shops and cafes.

I would have much rather rented one of the vacation rentals in Edgartown Martha’s Vineyard than where we stayed in Oaks Bluff.

It would have been nice to wander around this area at night. Just the few hours we had here in the day was one of our favorite things to do in Martha’s Vineyard.

There’s not a lot to do in Edgartown but walk and browse the shops and enjoy a vineyard gourmet fare.

Among the Flowers was a lovely cafe in town, where we had a delicious home made lunch on the patio among the flowers! For other Martha’s Vineyard restaurants ideas click here. 

Drive around the bay near Edgartown and you’ll find the wide open windswept, South Beach, where the opening scene for Jaws was filmed.

3. Edgartown Lighthouse

Walk about 10 minutes along North Water Street to admire the homes and visit the Edgartown Lighthouse which is set on the public beach.

You get panoramic vistas of Edgartown Harbor and over to Chappaquiddick Island.

Look back and check out the gorgeous Harbor View Hotel on the water here. If you want a hotel stay on Martha’s Vineyard, this would be one of the best hotels in Martha’s Vineyard.

Those views are something special and it looks very elegant and refined. If you can get a water view room, sunrises are meant to be pretty here. See it from the comfort of your bed even.

Check out reviews of Harbor View Hotel and book your stay through our partner, Booking.com

4. Get High Spirited in Oak Bluffs

Oak Bluffs Martha’s Vineyard is known for its high spirits and fun, which is what makes it a different experience to Edgartown on Martha’s Vineyard.

It’s main street is filled with restaurants, cafes and shops, including the popular brewery Offshore Ale and Johnny Cupcakes which my dad (John) just had to pose in front of.

It’s a pretty town with its Victorian homes and Oak Bluffs Campground, which is not your typical campground, nor is it opened to the public.

The campground is actually rows of extravagantly decorated historic summer gingerbread cottages.

19th Century Methodist would retreat here to worship in summer camps. They soon became residents and replaced their canvas tents with colorfully painted Gothic designed cottages.

More than 300 proprieties are now privately owned by descendants.

You can look from the outside or take a tour of the Cottage Museum  to glimpse inside. Free concerts and movie nights are held during the summer in the Tabernacle complex in the middle of the homes.

Take the drive to the East Chop Lighthouse high atop a 79 foot bluff with vies of Nantucket Sound.

On the East Chop Road, you’ll find many grey shingled mansions along the bluff road overlooking the sound. You can drive or walk along here.

In Oaks Bluff, grabbing the brass ring on the famous Flying Horses Carousel (the oldest operating platform carousel in the country), visiting Island Alpaca, and grabbing a tasty treat from Back Door Donuts came recommended as top things to do in Martha’s Vineyard.

5. Drive between Edgartown and Oaks Bluff

It’s a short scenic 6 mile drive between the towns of Edgartown and Oaks Bluff.

Along the way you’ll find The Bridge – you know the one from Jaws.

The stone quay Roy Scheider ran during the Jaws attack at the bridge is still there and runs perpendicular to the bridge.

Stop and jump off if you dare. It’s the thing to do in Martha’s Vineyard, you can even get T-Shirts that verify your triumph.

If the movie Jaws made me afraid of swimming pools then there is no way I’d take the bridge jumping challenge.

Even though I know Jaws was a six foot mechanical object, I don’t think I could bring myself to dip a toe. I’m not quite sure of the depth and my ability to land without hurting myself.

Although I did take bronze in the diving competition from the 4 meter platform representing Australia in our mock Commonwealth Games event.

You’ll also find Joseph A Sylvia State Beach, a 2 mile long sandy beach popular with families. This is where the beach scene from Jaws was filmed with all the kids swimming.

Parking is limited so it is better to go early or bike, walk or take the shuttle.

6. Visit Aquinnah Cliffs and Gay Head Lighthouse

Aquinnah is the official Native American township on the island and the Wampanoag tribe are the guardians of the region.

Previous to 1997, this area was known as Gay Head and is located in the south west corner of Martha’s Vineyard.

The town is best known for its terra cotta clay cliffs.

For over a 100 million years, glaciers, sea and land have twisted layers of soil into colorful, waving bands that are perched above the sea.

The Cliffs of Aquinnah are really beautiful.

I love the Wampanoag myth to explain the creation of these sacred cliffs.

Moshup, the giant Creator, would wade into the ocean, pick up a whale, fling it against the Cliffs to kill it, and then cook it over the fire that burned continually.

The blood from these whales stained the clay banks of the Cliffs dark red.

You can explore the lower beach paths to see the cliffs up close and stretch along the sands at Moshup Beach, or take the upper trails to the top of the cliffs to catch a glimpse of Gay Head Light and nearby Elizabeth Islands.

The cliffs are protected from erosion so no walking on them or collecting them!

The Gay Head Lighthouse is an iconic structure at the top pf the cliffs that you can also visit.

There are a few gift shops on the small bluff near the cliffs, which have a lovely collection of Native American jewelry or paintings, or handcrafts.

I highly recommend purchasing some for these unique and meaningful souvenirs.

We arrived in the morning to the cliffs covered in fog. We came back before sunset at Menemsha and it was clear and pretty.

It’s well worth the 30 minute drive from Edgartown. The locals told us you just never know what it’s going to do. Good luck!

If you’re staying over the other side of the island, I’d save a visit here until before sunset at Menemsha to reduce driving time.

7. Pair lobster with your Sunset at Menemsha

Menemsha on the west coast of Martha’s Vineyard is a quintessential New England fishing village.

We really enjoyed experiencing the sunset on Menemsha Beach on our last evening in Martha’s Vineyard. It was recommended to us as one of the best things to do in Martha’s Vineyard.

Behind the beach at Menemsha is a small fishing port with old boats tied up at the dock, weathered shacks, drying nets and lobster pots.

Eating freshly steamed lobster, brothy chowder or stuffed clam from one of the several fishing markets in the harbor is the thing to do for sunset.

You’ll see groups of people sitting on the rustic chairs on the dock eating lobster and drinking wine before they move over to the beach.

They close before sunset though so get in early!

Menemsha Fish Market was about to close, but they let us come in and order, but they had no lobster available.

Mum couldn’t stop raving about how delicious her fish burger was.

Craig and I shared a seafood nachos, which was really unique, but I think it needed some guacamole to give it a lift. You can’t have nachos without guacamole.

The main event in Menemsha is the gorgeous sunset.

There are plenty of rocks for the kids to scramble over while you watch the sun go down. I loved the giant bell ringing out in the water with each movement of the ocean.

It felt very Jawsish!!

But this sunset should probably go at the top of our Martha’s Vineyard things to do list!

If the harbor looks familiar, it’s because several scenes from the Jaws was filmed here.

Menemsha Hills is also recommended  for it beautiful hiking trails and high elevations.

8. Vineyard Haven

You may get confused on the island as to where the dividing line between Tisbury and Vineyard Haven is. There is none.

Vineyard Haven is Tisbury.

It’s actually the name of the ferry port, so most people call it Vineyard Haven, but it is Tisbury.

On the elegant to rowdy scale, it sits somewhere in the middle between Edgartown and Oaks Bluff.

You’ll find plenty of stores to browse in the small town here and the drive from Oaks Bluff to here along the coastline is quite pretty.

If you’re looking for gluten free food for your home cooking supplies, you must visit Vineyard Grocer, located in a cute red barn on the main road.

We were impressed with the amount of gluten free and healthy food here, and for a decent price too considering where it is located.

On the drive between Vineyard Haven and Menemsha, you’ll find the Scottish Bakehouse. Gluten free lovers you’ll be so happy with the variety of gluten free sweets and bread – it’s a rare treat for us!

Except for Oak Bluffs and Edgartown, the Vineyard is “dry,” but many restaurants allow you to bring your own beer or wine.

The town of Vineyard Haven allows beer and wine – but no liquor – sales in restaurants only.

Do you need a car on Martha’s Vineyard?

We took our vehicle over on the car ferry to Martha’s Vineyard. As we visited outside of peak time, we didn’t experience traffic problems or difficulty parking.

It’s meant to be a nightmare during the peak summer months, and through my research, I learned that it’s best not to take your car over to Martha’s Vineyard if you can get away with it.

It will be cheaper on the ferry and the public bus can take you around to different parts of the island.

Where you choose to stay will be very important to you then if you don’t have your car. You want to stay in the area you most want to spend time in.

I’d recommend taking bikes if you have them as you can get around easily enough on them in the area you are staying in.

It is 6 miles from Oak Bluffs to Edgartown which would be about a 40 minute bike ride.

How Big is Martha’s Vineyard?

The island is roughly triangular-shaped with its base the straight south shore, and northern points facing Cape Cod.

It is 9 miles (12.8k) wide and 26 miles (40k) long at its furthest points; the total land area is approximately 96 square miles.

The longest drive would be from Oaks Bluff to Aquinnah which is 19 miles and would take approximately 40 minutes.

Where to Stay on Martha’s Vineyard for Families

We stayed at a cottage we found on Glamping Hub located  in a quiet neighborhood between Vineyard Haven and Oaks Bluff.

It was cute and comfortable with everything we needed in the kitchen.

I thought it was overpriced compared to other places we’ve stayed at before via Glamping Hub or Airbnb, but I think accommodation on Martha’s Vineyard is more expensive in general.

If you plan on visiting Martha’s Vineyard with kids, especially in the peak season, be sure to book your accommodation in advance as far as you can.

For other places to stay in Martha’s Vineyard, our affiliate partner, Booking.com has over 70 properties listed in Martha’s Vineyard.

You can also search for home rentals on Airbnb.

Actually, now that I’ve written this post and looked back at the photos and the memories, Martha’s Vineyard is a pretty island and a great spot for a relaxing family vacation.

Isn’t it funny how sometimes you appreciate a place more after you’ve left it?

Bonus Martha’s Vineyard Video

Need More Tips for Massachusetts?

Start here:

• How to see a Boston Red Sox game at Fenway Park
• Walking the Freedom Trail in Boston
• City Guide – What to do in Boston
• 17 Legendary Things to do in Boston MA with Kids (or without)

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Do you have any further tips for Martha’s Vineyard, things to do, or otherwise?

I knew it would be inspiring and informative as you follow and learn so many monumental and historical events that helped America gain its Independence from Great Britain.

But, I wasn’t expecting humor.

Our guide, Isiah Thomas, (played by Rob Crean) was dressed in 18th-century clothes – stockings, cloak, three-cornered hat – and was hilarious.

He had the kind of dry sense of humor that us Australians relate so well to. I’m pretty sure that my Dad was the person laughing the most on the tour.

Even when it wasn’t out loud, I could tell he was laughing so hard on the inside at Isiah’s off handed comments that said so much.

The stories he told were quite serious but it’s all about the delivery. He delivered with such entertainment that we were all disappointed when it ended.

The stories seemed that crazy and were so funny, I wasn’t sure if he was just making them all up. One thing is for sure, I learned a lot about Boston, the Revolutionary War and all its heroes and villains on this tour.

How can you forget stories that are delivered in such a fun way.

Be prepared to learn the truth about Paul Revere, the hero who rode for miles and miles to let the Americans know the British were coming and to save them from their eventual arrest, which would have been for treason and would have ended the patriots attempts to overthrow British rule.

What a different story that would have made?

All of that happened in Boston, one of America’s most historical and oldest cities.

Well the Paul Revere story, as most children learn through the poem written by Henry Longfellow, is incorrect.

Many parts of the story were changed for poetry’s sake – you know to make a line rhyme better!

I was shocked as I remember my students learning this story through the poem as well. We’ve all been lied to. Someone had to be made the hero and Longfellow’s abridged story fit the poem better.

The telling of the true story was hilarious and brought the calamity of the truth to light.

But, let’s still honor Paul Revere as he did play a part in helping America become America.

The Boston Freedom Trail Tour

How long is the Freedom Trail? The Freedom Trail in Boston is a 2.5 mile long red line through the city.

It comprises a unique collection of museums, churches, meeting houses, burying grounds, parks, a ship, and historic markers that tell the story of the American Revolution and beyond.

It was in Boston that the American Revolution began and is what makes this city so fascinating and unique.

Experiencing the Boston Freedom Trail Foundations Tour is one of the must not miss things to do in Boston.

You can walk and follow the Freedom Trail on your own, or you can take a Freedom Trail tour led by 18th-century costumed Freedom Trail Players for insider tales of high treason, mob agitations, revolutionary actions, and partisan fights of the American Revolution.

Each guide is a legendary figure at the forefront of the American Revolution. Isiah Thomas was the publisher of the Massachusetts’s Spy.

The Walk Into History Tour is a 90-minute tour featuring 11 of the 16 Freedom Trail sites.

The Reverse Walk Into History Tour is the same tour, beginning and ending in the reverse locations.

The North End tour is a 90-minute tour featuring 3 of the 16 Freedom Trail sites, as well as the North End neighborhood (one of our favorite areas in Boston).

Some of the historical sites in Boston that we passed and heard stories about on our walking tour were the State Capitol Building in the distance sitting up on Beacon Hill, the Old State House and the site of the Boston Massacre and where the Declaration of Independence was read from the balcony in 1776.

We also spent time in the Granary Burying Ground, where we saw several important Revolutionary heroes buried, including John Hancock and Sam Adams.

Across the road is the Beantown Pub, which is the only place in the world you can drink a cold Sam Adams overlooking a cold Sam Adams – pretty cool.

We attempted to go back and do that after the tour but it was too busy.

If you walk the Freedom Trail on your own, the trail is marked with a painted or bricked red line that is easy to follow. Signs along the Freedom Trail identify each of the 16 historical stops.

Allow at least three hours to take a leisurely pace and enjoy all the historical markers.

Is the Boston Freedom Trail Tour kid friendly?

It was quite a hot day when we did the Boston Freedom Trail tour and we had spent the morning on the Duck Tour and doing a fair bit of walking.

I was concerned the girls would have a meltdown.

But, we found shady spots along the way, and our 10 year old Kalyra said she really enjoyed the tour. She was attentive and curious.

The full tour may be a bit long for younger kids, but if they love history, it’s a fantastic Boston attraction to do with kids.

It’s so informative and funny and will sure beat learning about it in those way too thick and boring history books.

The guides are dressed up and take on the persona of a character from the Independence period which is engaging for them.

These are the types of things we love to do to help road school our kids.

We let interactive real life experiences teach them. It means we have more time to pursue passions and talents and to spend together creating memorable moments.

You can read more about how we road school here.

Boston Freedom Trail Tours:

Bonus Boston Travel Video:

Where to Stay in Boston

We rented an apartment located in the South End area through Booking.com.

The South Boston Family Getaway at West Square Apartments was modern, beautifully furnished, comfortable and spacious.

Our two bed apartment slept the six of us, with two large bedrooms and a sofa bed for the kids.

It was easy for us to get around different parts of Boston and was a 40 minute walk into the city.

I’d stay there again.

Read reviews and book your stay through our partner, Booking.com

For more places to stay in Boston, click here.

More Tours of Boston:

Viator is a Trip Advisor company and offers small group tours of Boston to the most popular places and attractions.

More Tips for Massachussets:

• City Guide – What to do in Boston
• How to see a Boston Red Sox game at Fenway
• How to spend 3 days in Martha’s Vineyard

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I’ve always been a bit ho hum about baseball.

I think I may have fallen asleep at a game once, and I definitely spent time reading the newspaper at a LA Dodgers game.

The only thing that saved baseball for me is the Seventh Inning stretch, and hot dogs and beer. Both of which I can no longer have because of gluten.

However, I did enjoy baseball more last year when we went to an iconic Durham Bulls baseball game near our home in Raleigh.

I’m not sure if that was more to do with the gluten free beer we had before the game and the jovial atmosphere of hanging out with friends.

But, on our recent trip to Boston and watching a Boston Red Sox baseball game at historic Fenway Park, I was hooked and ready to make baseball a family summer tradition.

For any international visitors to the USA, I recommend you take in a baseball game and experience this side of American culture.

Just like cricket for us Australians, baseball is more than just watching the skills on the field; the experience surrounding it is half the fun too.

Fenway Park in Boston, Massachusetts buzzes with spirit and atmosphere. It’s the oldest baseball park in the country, so it’s had time to grow a hard core Red Sox fan base.

Since 1912, it has been the home for the Boston Red Sox, and the intimacy of this field makes the baseball experience at Fenway Park even more special.

Boston Red Sox baseball game vs Atlanta Braves

The Red Sox were playing the Atlanta Braves.

Living in Raleigh, you could say Atlanta is really our Southern team for the Major Leagues as there are no teams in North Carolina. And seeing the Atlanta Braves play was also our very first baseball experience back in 2005 in Atlanta.

However, for this game, we were supporting the Red Sox all the way.

Sorry Atlanta, but it’s Fenway Park and us Aussies don’t necessarily bear allegiance to any team.

We couldn’t have gotten a more perfect day for our baseball game at Fenway Park. It was bright, sunny and warm, and our tickets magically placed us in the shade behind the left field.

As the stadium is small for Major League standards, capacity of 37,731, you really can’t get a bad seat at Fenway Park.

I was worried the girls might get bored and whiny, but they loved the experience of it too, particularly Savannah. She watched intently and asked lots of questions, quickly figuring out the general gist of the game.

And there’s a small kids zone area near K Gate at Fenway Park, which has virtual reality games and simulated pitching and batting.

It was busy so the girls just had a quick dug out VR game while they walked around the stadium with Craig and my Dad during the game to stretch their legs.

Mum and I stayed watching, I only got up once to get the girls a bucket of popcorn and after our one month road trip from Dallas to Boston, and visiting countless attractions, I was glad to sit down for half a day and watch a game of baseball.

The Green Monster

The big thing to experience at a Boston Red Sox baseball game at Fenway Park is the batter hitting the ball over the famous Green Monster.

The Green Monster is an iconic 37 foot wall, originally built to prevent free game peeking from those in the street behind the park.

It wasn’t until it was painted green in 1947 that its reputation as the Green Monster and the place to hit a home run began.

The Red Sox recognized that it would be a sought after place for fans to seat so with lucrative business eyes on they installed 269 seats atop of the Green Monster in 2003.

The fans love scrambling over each other to catch one of the balls flying up into the Green Monster from the home plate 310 feet away.

It’s the highest wall in the country for Major League baseball fields.

When 37,000 people sing your song

I was warned by friends just before we arrived at Fenway Park that there would be a special treat for me – a Fenway Park Red Sox tradition.

At the bottom of the 8th innings, the crowd breaks out into a rendition of Sweet Caroline! There’s something pretty special about a stadium filled with 37,000 people singing your song.

I think it made my Mum and Dad’s day too!

Dad’s never been a great baseball fan either being from Sydney, but he is a huge sports fan especially cricket, which has some similarities.

As he said, there’s nothing like watching a game live, so you can see the skill involved and feel the atmosphere.

Mum really loved the Fenway Park baseball experience as well, and she got into the Seventh inning stretch and Sweet Caroline singing and dancing in our seats.

Watching the baseball at Fenway Park was a memorable family experience for us on our Dallas to Boston Road trip.

I think my parents will even follow the Red Sox path to victory (we hope) this year from back home.

We were lucky to experience a few Green Monster hits and a Red Sox win! The crowds were enthusiastic and jovial and because the game was fairly close it made it pretty interesting.

Going to a Red Sox game at Fenway would have to be one of the best things to do in Boston with kids (or without kids, lol).

After the Red Sox game – hit the Fenway Park bars

Before you leave the Red Sox game, don’t forget to buy a hat, or a t-shirt.

We love buying baseball caps of memorable travel experiences. It brings back happy memories whenever we wear it and often leads to great conversations with strangers.

Dad and I bought B hats as Fenway Park was an experience both of us wanted to forever remember.

Mum and Dad took the girls back to our apartment after the game so Craig and I could  have the complete Fenway Park experience and check out the bars surrounding the stadium.

They have legendary status like the stadium itself.

The most popular Fenway Park bars before the game are Cask ‘N Flagon, Game On, The Lansdowne Pub, Tony C’s Sports Bar & Grill, Boston Beer Works, and the Bleacher Bar.

It is better to go to the bars before the game, but they will be packed and it didn’t work out for us.

Most people clear out of the bars and go home after the game so you do have a little more space in the bars.

The Bleacher Bar

Don’t miss the Bleacher Bar, which has a dugout bar on the edge of the field.

If you want to watch a baseball game at Fenway Park for free then this is the bar to go to.

You can see the game through the wire mesh. I don’t think it would be as good, but it’s an option as tickets to the game may be hard to get or expensive.

Fellas, don’t miss the view from the restroom. Over the trough is a window which allows you to continue to watch the game as you do the business.

Spotted by me as I turned around and saw this head with a look on the guy’s face that told me exactly what was going on.

I’ve seen my babies pee enough times to know that look. Ew!! I don’t want to watch someone peeing.

Maybe get someone to take a photo of you though as it is certainly unique! Anyway, Craig just had to snap a pic for you!!

Friendly locals

Seriously though, America is the friendliest place in the world.

We visited three bars on our night out in Boston with out the girls, and barely spoke to each other as we met several locals who were happy to sit at the bar and swap stories with is all night.

My parents also could not get over how friendly everyone is and how many random conversations we had with people.

People who didn’t even know we were Australians but would stop to talk to us because we’re wearing North Carolina Tar Heel caps, or Durham Bulls T-Shirts or had NC license plates on our car.

It makes traveling and going out so much fun.

How to Get to Fenway Park

We recommend walking along Newbury Street from the city before the game.

It’s only a 30 minute walk from the beginning of Newbury street at Boston Public Gardens to get to the stadium.

Newbury Street is the prettiest high end shopping street I’ve seen in the US – better I think than 5th avenue in New York and the Magnificent Mile in Chicago.

Otherwise there are T-line stations nearby, or catch a Lyft or Uber. As there were six of us, it was cheaper to get Lyfts around Boston.

We stopped for coffee at Barrington Coffee Roasters during our walk to Fenway before the game.

And for a quick and cheaper meal before the game, grab a burger at Wahlburgers which is right near Fenwway who have healthy burger options for us, and hot dogs for the kids.

Otherwise it might be more fun to eat at Cask N Flagon to soak up the Fenway Park atmosphere magic.

Tickets for the Baseball at Fenway Park

The Go Card Boston Premium Pass covers a baseball game at Fenway Park and will also give you access to other Boston attractions such as the Freedom Trail, Paul Revere’s House and SkyWalk Observatory.

It might be a great option to save money if you plan to visit a few Boston attractions. Get your pass here. 

You can also get tickets direct through MLB.

Fenway Park Walking Tour

Why not do a game day tour of Fenway Park to make this unique baseball experience at America’s most beloved baseball stadium even better?

We didn’t do this, but it would be a great tour for families, and all Red Sox fans!

Two hours before the game you’ll get to do a walking tour of Fenway with access to the field during the team warm-ups, head to the top of the stadium’s famous “Green Monster” outfield wall, visit the famous “Pesky’s Pole,” and learn about Red Sox legends like Ted Williams, Carlton Fisk, Jim Rice, and Carl Yastrzemski (“Yaz”).

Learn more and book through Viator. 

Where to Stay in Boston

We rented an apartment located in the South End area through Booking.com. The South Boston Family Getaway at West Square Apartments was modern, beautifully furnished, comfortable and spacious.

Our two bed apartment slept the six of us, with two large bedrooms and a sofa bed for the kids.

It was easy for us to get around different parts of Boston and was a 40 minute walk into the city.

I’d stay there again.

Read reviews and book your stay through our partner, Booking.com

For more places to stay in Boston, click here.

Need More Boston Tips?

• Walking the Boston Freedom Trail
• City guide for Boston
• 17 Things to do in Boston with kids
• Boston Harvard University Tour showcases possibilities

New England travel tips

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Have you been to a Boston Red Sox baseball game at Fenway Park? Or any other basbeall game? Share your experience in the comments.

This is your hub for all the best places to visit in MA, including top Massachusetts attractions, cool cities and small towns, historical experiences and unique outdoor adventures.

You’ll find our best tips, recommended hotels, tours and deals. We’re adding to this the more we explore Massachusetts, so keep checking back.

Be sure to check all of our USA travel tips, as we’ve been exploring the country in-depth for the past year on short breaks, getaways, road trips, and a year long RV trip of the American West.

What are your favorite things to do in NC?

As you can see from the comments, we already have so many wonderful tips on places to visit in MA. Please shares yours as well!

Sure, when we visit Massachusetts we still want to see the obvious Massachusetts vacation spots, but can you suggest other places to visit in Massachusetts? What are your best things to do in Boston? 

Some things already on our Massachusetts bucket list include:

• Boston
• The fall colors of New England
• Cape Cod
• Martha’s Vineyard

Boston Travel Tips

Boston has to be one of our favorite cities for its unique English charm and history, it’s vibrant sporting life, and friendly people!

• 17 legendary things to do in Boston with kids
• Boston Harvard University tour – well worth it
• The historic and hilarious Boston Freedom Walk Tour
• An iconic US experience – baseball at Fenway Stadium with the Red Sox

Boston videos

See all the fun we had exploring this amazing city.

Other MA destinations

Still so much to explore, but here is the charm we’ve already discovered!

• How to spend 3 days on Martha’s Vineyard – things to do!
• 7 Helpful tips for a New England road trip in the Fall
• Things to do in New England – 10 Small towns not to miss

A quirky roadside attraction

Technically, America’s Stonehenge is in New Hampshire, but it’s right on the border of Massachusetts and it’s just too good not to share!

As part of our city guides series, we interviewed Kate McCulley who grew up about 20 minutes north of downtown Boston.

Kate shares with us her insider tips on what to do in Boston for those looking for the Boston highlights and the best places to eat, sleep, explore, shop, and party.

What to Do in Boston for first time visitors

Go to a Boston Red Sox basbeall game!

Sing Sweet Caroline, do the wave, and start a “Yankees Suck” chant. Believe me, you’ll love it even if you’re not into sports — it’s a cultural experience!

Be sure to follow the Freedom Trail from Boston Common to the North End, or even the Charlestown Navy Yard if you’re up for a longer walk. It shows you most of Boston’s most famous historical sites.

Take a ride on the swan boats in the Public Garden if you’re visiting during the summer.

Best Neighborhoods to Explore in Boston

Boston is a city of neighborhoods. Be sure to check out the North End, Boston’s historically Italian neighborhood. Cross the river and get intellectual in Harvard Square.

The South End is a beautiful neighborhood and one that not a lot of tourists explore.

Where to Eat in Boston

If there’s anything I can talk about all day, it’s food in Boston!

It seems like Boston has a million burrito joints.

• My favorites are Anna’s Taqueria and the Herrera’s street cart in Downtown Crossing.
• Quincy Market has lots of cheap food stalls. I always make every visitor go to Modern Pastry in the North End — NOT Mike’s Pastry across the street — and have a cannoli. They make great chocolate cheesecake, too.
• Bottega Fiorentina is a shockingly cheap Italian restaurant and deli in the middle of pricey Newbury Street.
• Flour is an amazing bakery and they make killer homemade Oreos and cornmeal lime cookies.
• For a special night out, I LOVE Cuchi Cuchi in Cambridge. It’s the girliest restaurant ever — the staff wears costumes from the 20s-50s, they serve vintage cocktails and small plates from around the world, and the decor is eclectic and features a giant sparkly mermaid. Try the Guatemalan seafood avocado.
• A  few other great upmarket restaurants: Union, the little black dress of Boston dining (you’ll get it when you go there).
• Coppa, the best place for Italian cured meats and where I’ve celebrated my last two birthdays; and Toro, the city’s best tapas place and home to some incredible corn.

Where to Drink in Boston

• 28 Degrees is an incredibly stylish martini bar in the South End and home to the world’s best frozen Bellini. Be sure you check out the cool bathrooms, too.
• Eastern Standard is an upscale restaurant, but the bar is THE place to be for 25-40-year-old professionals on Sunday nights.
• Boston is covered with Irish pubs, both authentic and not-so-authentic — you’ll find actual Irish servers, bartenders, and musicians at The Burren in Davis Square.
• Where to Drink with the Locals in Boston:
• Hit up legendary sports bar Cask’n Flagon during a Red Sox game and you’ll REALLY get a taste for Boston!
• If the Red Sox are in town, check out the Bleacher Bar across the street — which is actually inside Fenway Park and lets you watch the game without paying for a ticket!

Where to Stay in Boston

The HI-Boston hostel is in a perfect location, right by Back Bay and Fenway Park. I should know, I used to live a block away.

For high-end, you need to go to the Liberty Hotel, formerly the Charles Street Jail. They have preserved the jail theme so well – the bars are called Alibi and Clink and feature jail bars and celebrity mug shots — and its style is off the hook.

It’s THE place to be most nights, particularly if you’re looking to pick up a surgeon or hedge fund manager.

For more places to stay in Boston choose from the largest range of hotels, apartments, and guesthouses with our partner Booking.com. 

Best Markets & Shopping in Boston

The Faneuil Hall Marketplace is loads of fun, though most locals wouldn’t be caught dead there. I kid, I kid. It’s fun.

If you’re into cool little boutiques and vintage shops, I recommend Newbury Street in Back Bay (closer to the Mass. Ave. end), Charles Street in Beacon Hill, and Tremont Street in the South End.

Events & Festivals in Boston

No city in America does the Fourth of July better than Boston, with the Boston Pops and Pops Goes the Fourth concert!  If you want to watch the concert on the Esplanade, get there early — think 9 AM — and stake out a good spot. Same for seeing the fireworks.

Marathon Monday, the day of the Boston Marathon, might as well be a holiday. Everyone goes to cheer the runners on. My favorite spot is at the final corner, on Boylston St. at Hereford St. in Back Bay — the runners get SO excited as they make that final turn.

Best Area for a Night on the Town in Boston

It all depends on what you’re looking for.

If you’re into live music, check out the further-out neighborhoods of Allston or Somerville. If you want to hit the big clubs, head straight for the Theatre District.

Personally, I love the hip atmosphere, cool restaurants, and smaller dance clubs of Central Square in Cambridge.

Boston is America’s Walking City. It’s very easy to get around on foot and the T (the subway), and I think that’s the best way to see Boston.

There’s nothing better than a stroll across the Mass. Ave. bridge and down Marlborough Street in Back Bay on a warm summer afternoon, admiring Boston’s beautiful architecture.

Finding WiFi in Boston

It’s not as good as I’d like, but it’s getting better. You’ll find WiFi in most cafes; restaurants are slowly catching up.

Websites & Resources for travel to Boston

Sign up for Gold Star Events before your trip — they have half-price tickets to sports games, museums, and performances throughout the city.

Favorite Side Trip from Boston

Drive up to the North Shore and see some nice seaside towns — Rockport, Newburyport, and Salem. My favorite town is actually over the state border: funky Portsmouth, New Hampshire.

Best Time to Visit Boston

Fall is absolutely beautiful with the leaves changing. Summer is very hot and humid — I personally can’t get enough of it, but it’s not for everyone.

Avoid winter if you can. The snow lasts all winter and makes it hard to get around on foot, which is a shame, as long walks are one of the pleasures of visiting Boston.

Getting There & Away

Flights to Boston: Budget airline Southwest now flies to Boston from all over the country.

You can also get super-cheap bus tickets from New York on the Megabus or Bolt Bus — the ride is about 4.5 hours.

The train is very expensive, but you can occasionally find deals from New York, Philadelphia, or Washington, DC.

Best insiders tip for Boston

Southwest Corridor Park. It was originally supposed to be a highway, but the highway never happened, so it became a park that winds all the way from Back Bay to Jamaica Plain.

In the Back Bay/South End portion, you’ll find beautiful greenery and dog parks sandwiched between rows of immaculate brownstones. It’s one of my favorite places in Boston to get away.

I Love Boston because …

It’s the best place in the world to take a long walk!

Boston Travel Videos

Need More Boston & Massachusetts Tips?

Start here:

• 17 things to do in Boston with kids
• How to see a Boston Red Sox game at Fenway Park
• Walking the historic Freedom Trail in Boston
• How to spend 3 days in Martha’s Vineyard

Planning a Trip to Boston

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BIO: Kate McCulley grew up 20 minutes north of downtown Boston. After college, she lived downtown for four years, and then quit her job to go traveling. Kate runs the popular solo female travel blog Adventurous Kate, the story of how a twenty-something girl from Boston decided to upend her life to travel the world.

Do you have any tips on what to do in Boston? Please share in the comments.