Boston is a beautiful city to visit and a great place to go for a family vacation. The capital of Massachusetts and largest city in New England is rich in historical sites, cultural diversity, memorable locations, and fascinating stories.
I lived in “Beantown” for a few years in my early 20’s and the city still holds a place in my heart. When I brought my family for a visit last summer, it made me so happy to be back. A lot has changed since I was last there, but the things that I loved about Boston remain. It’s still one of my favorite cities!
Why Visit Boston with Kids?
Boston has a lot to offer for the whole family looking for an unforgettable vacation. It’s a lovely and walkable city, with a lot to see and do, neighborhoods to explore, history to learn, and delicious foods to eat.
The city is located on the harbor, so kids can see the ocean and ride boats, visit world-class museums, and taste fresh seafood and ethnic cuisines. Boston and Cambridge share a river and there are plenty of green spaces, parks, and gorgeous historic brownstones. It’s one of the most beautiful cities in the United States!
I highly recommend that you visit when the kids are old enough to learn and appreciate its history. Also, it’s best to explore Boston on foot, so make sure the kids are able to walk for a bit.
When is the best time to visit Boston?
Summer is the best time to experience Boston. June through September are the warmer months in which you’ll get the sunniest days, bringing in the glorious beauty of the city and ability to walk without getting cold and wet!
Here are my Top 5 recommendations for sights and things to do that are unique to Boston!
1. Walk the Freedom Trail on a historic walking tour
The Freedom Trail, a 2.5-mile red brick trail lining the middle of the sidewalk, takes you to various historical sights in downtown Boston and Charlestown.
Monumental events that defined the struggle for freedom and eventual formation of the U.S. in the 1700s took place in Boston. The historical sights of Revolutionary Boston are highlighted on the Freedom Trail, including:
Boston Common. This historic green space is the nation’s oldest public park and was used for cattle-grazing and soldier encampment.
Old Granary Burial Ground. Final resting place of Paul Revere, John Hancock, Samuel Adams, and other important figures in the American Revolution.
Old South Meeting House. The largest building in colonial Boston, this was a gathering place to protest British rule, the Boston Massacre, and the tea tax.
Old State House. Built in 1713, this landmark housed the colonial and state governments. Out front is where the Boston Massacre happened, commemorated by a cobblestone circle.
Old Corner Bookstore. Now a Chipotle, this original building was built in 1718 as an app the art and became a literary center for famous authors to publish their manuscripts.
Go on a historic walking tour with a costumed local guide!
It’s easy enough to grab a map and do a self-guided tour, but I highly recommend going on a walking tour with a local guide. The experience is even better when the tour guide is in full costume (ours was dressed as Mother Goose)! Tour guides will keep kids engaged because they are natural storytellers with a passion for their city’s history.
Free walking tours are available, but I have never gone wrong with paid tours with Viator. The local guides are fantastic and give a unique perspective on living in the city as well as all the fascinating history that has taken place there.
2. Walk the Black Heritage Trail
The Black Heritage Trail is not as famous as the Freedom Trail, but the history is just as fascinating with the pursuit of equality and freedom for African-Americans in Boston. It is a shorter trail (1.6-miles) around the Beacon Hills neighborhood that includes houses of the Underground Railroad and the first integrated schools. In the decades leading up to the Civil War, half of the city’s blacks lived on Beacon Hill below the homes of wealthy whites. Highlights of this trail include:
54th Regiment Memorial. This impressive bronze piece lies across from the new Massachusetts State House and tells the story of the all-black regiment that fought in the Civil War under Colonel Robert Gould Shaw (which the movie Glory was based on).
Hayden House. Lewis Hayden was born enslaved in Kentucky and escaped with his wife Harriet to Boston, where he became a leader in the abolition movement. Their house was an integral stop on the Underground Railroad.
3. Attend one of Boston’s special events or cultural festivals
Boston comes to life during celebrations and special events. Ask anyone who has been in Boston during the 4th of July, the Boston Marathon, or after the Boston Red Sox won the World Series! Boston residents are loud and proud of their city.
If you happen to be in Boston during 4th of July or another special event, you’re in for a treat! Although it can get crowded and noisy during these times, it’s really fun and you get a true sense of the spirit of Boston.
Check out the vibrant multicultural Boston at a festival
Boston is home to international students, immigrants, and business people from all over the world, lending to a vibrant multicultural community. There’s no better way to experience the diversity and spirit of Boston than to attend one of its many cultural festivals offered, especially in the summer months.
You can also check out different neighborhoods in various parts of Boston to “go around the world” and experience food and culture from the Dominican Republic, Brazil, Puerto Rico, Korea, Cape Verde, China, etc. There are even unique fusion restaurants such as Ethiopian/Vietnamese!
Live Like a Local tours offer food and other unique tours that explore food history, and culture in off-the-beaten path from the major sights in Boston.
4. Watch a Red Sox baseball game in Fenway Park
Fenway Park is the oldest ball park in the United States, so attending a ballgame during your visit is like going back in history. Even if you don’t particularly enjoy baseball, being in the old-school stadium and feeling the Boston vibes is a cool experience that can’t be missed.
After a day of sightseeing, there’s no better way to spend a summer evening than sitting in the ballpark with a view of the flashing Citgo sign and feeling the cool air with brews and brats in hand. You will not have more fun sitting down! Get ready to stand up for the wave and sing-a-long to “Sweet Caroline”!
5. Visit the U.S.S. Constitution Ship & Museum
The U.S.S. Constitution, or “Old Ironsides”, is the actual ship built in the 1790’s. Famous for its sturdy construction and undefeated record in various battles, you can get onto the ship for free and also go below deck. My kids also liked seeing the jellyfish in the water after getting off the ship.
An interactive museum lies across from Old Ironsides and tells the story of life on the ship, how the ship was built, and its historical significance. It’s a great museum for kids for all ages because they have award-winning exhibits including games to play (electronic battleship and design-a-ship), hands-on programs with guides, rare artifacts, and interactive visuals.
This sight impressed me which was surprising since I didn’t think I liked things like big ol’ iron battleships and war. However, the museum was really fun and the ship itself is stunning. It’s a must-see while you are in Boston!
6. Eat Seafood. Lots and lots of seafood.
Whether you go for a lobster roll, steamers, oysters, New England clam chowder or smoked fish spread on a bagel, Boston has plenty of delicious options for any seafood lover.
Dig in and enjoy, especially if you live in a place where it’s hard to get fresh seafood!
Seafood Restaurants to try:
- Barking Crab – somewhat touristy, this landmark in the historic Fort Point Channel is a fixture on the waterfront and gateway to the Seaport District. This original clam bar now serves lobster rolls, fried clams, steamers, mussels, and crab cakes and more under a tent lined with picnic tables.
- Union Oyster House – this seafood restaurant is America’s oldest restaurant! It has been serving food since 1826 and has the same rustic feel of the pre-revolutionary wary days.
- Legal SeaFoods – this popular place has multiple locations and is famous for its tag line “If it isn’t fresh, it isn’t Legal!” Fresh seafood (try the signature crab cakes, lobster Mac and cheese bake) and a cute kids menu makes this a favorite for families.
- Boston Sail Loft – located on the waterfront, this seafood restaurant came highly recommended by a local friend for a special occasion or anytime to get its award-winning clam chowder, lobster ravioli, lobster roll, and more
- Ivory Pearl – located up the green line in Brookline, this New American cocktail bar offers the Seafood Tower, a tiered plate of oysters, shrimp, crab legs and caviar. A splurge.
Tip: AVOID getting fresh seafood from Quincy Market
Other things to do in Boston during a family vacation
Visit the Boston Common & the Boston Public Garden
The two parks in the middle of the city have it all – history, tall trees, green grass, a pond with boats, bridge, and wildlife (birds and squirrels). Take a couple of hours to walk around, sit on the benches, and watch the swan boats go by.
Notable features to check out in the parks are the George Washington statue, Make Way for Ducklings bronze statues (based on the popular children’s book), frog pond (empty during our visit in the summer but converts into an ice skating rink in the winter), and the bench during the scene in “Good Will Hunting” where Robin Williams’ character gives Will an earful about life. The Visitor Center is where the Freedom Trail and Black Heritage Trail tours originate and also sells cute gifts and souvenirs.
Go on a Swan Boat Ride in the Public Garden
The iconic swan boat has been operating since 1870 and is still a non-mechanized paddle boat just like in its heyday. Although it’s a bit slow, riding the swan boat is perfect for young kids and older adults who want a calm and relaxing ride on the water.
Check out Acorn Street in Beacon Hill
Known as the most photographed street in the United States, this narrow cobblestone street in Beacon Hill is one of the oldest inhabited streets in the United States. With its gorgeous brick brownstones, quaint windows, ornate doors and little pieces of history, this street is worth taking your own pictures!
It’s also worth checking out the surrounding neighborhood of Beacon Hill. The homes on Beacon Hill have the highest real estate costs of any area in the city. The homes are beautiful, and it brings you back in time as many of the structures are the originals built when the Europeans settled there in the 17th century.
Visit the Bunker Hill Monument
The Bunker Hill monument is a tall, obelisk-shaped tower standing on the top of the hill in Charlestown, across the river from Boston. The monument itself is visible from many parts of Boston (and when you cross the bridge to go to Cambridge), but it’s worth a short stop if you love American history.
The Battle of Bunker Hill took place here and was an important battle fought during the American Revolution. The audio tour and museum highlight the battle and how the surrounding community came together to stand up against the British.
Go Kayaking along the Charles River
The Charles River divides Boston and Cambridge. On any given day, you’ll see the river bustling with crew teams, boats, and kayaks. It is a place to spend a few hours enjoying the water and views of both sides. If you don’t actually want to get in the river, then you can take a stroll along the Esplanade (path on the Boston side of the river).
Visit Harvard Square for the college campus and ethnic eats
Harvard Square is home to the oldest university in the United States, in addition to being a nice place to spend a few hours. Visit the Harvard University bookstore and the quirky shops in the Garage and Atrium shopping malls. You can also grab a coffee, cannoli, or a bite to eat at any of the cafes or restaurants offering ethnic cuisines.
A free tour of the Harvard University campus is available by college students themselves. The campus is beautiful with large, leafy trees, majestic brick buildings, and the vibrant feel of the campus. Don’t miss the statue of John Harvard, Harvard Yard (don’t forget to practice your Boston accent by saying “I pahked my cah in Hah-vahd Yahd”), and the Museum of Natural History.
Eat a Cannoli in Boston
Apparently, eating these Italian desserts is a thing in Boston. Although I’d rather go to Italy to get the real deal, my sweet-toothed daughter kept asking to try these tasty cream-filled treats.
Mike’s pastries is the most well-known and has multiple locations. For a more authentic experience, go to the North End for a cannoli.
Visit the fun Boston Tea Party Ships & Museum
This little museum on the Boston harbor is fun and engaging for the kids. Costumed character actors reenact the events leading up to the Boston Tea Party. In addition, cool holographic pictures, a multi-sensory documentary, and historic artifacts bring the famous event back to life!
Although the ship itself isn’t the real deal, the museum has all sorts of interactive exhibits to enhance the experience. The highlight for most kids is throwing a box of fake tea over in the same body of water where the Boston Tea Party took place in 1773.
Check out the family-friendly museums in Boston
Boston has many amazing museums, and families with children of all ages will find something they will enjoy. From art to science to interactive hands-on museums – Boston has them all. Here are the top recommendations in order of my preferences:
Museum of Science
Huge, nicely-laid out museum with Dinosaur exhibit, planetarium, IMAX, and other interactive exhibits for kids of all ages and parents who like science and history! You can easily spend 5 hours here so choose this museum on a rainy day!
New England Aquarium
The New England Aquarium is a popular choice for families, and the major draw is the giant glass tank with a spiral walkway. The aquarium houses many species of fish, turtles, and penguins. It also has an interactive stingray petting experience and shark exhibit. Feeding times by the scuba diver is also interesting to watch!
Boston Children’s Museum
for kids 11 and under, this museum offers fun, hands-on educational exhibits.
Isabella Stewart Gardner Museum
one of the most unique and beautiful art museums I’ve ever been to. Aside from the art, the building is reminiscent of xxx. Also, a daring art theft happened here in
Museum of Fine Arts
Egyptian exhibit with mummies, Van Gogh, Monet, and contemporary art.
Admissions to museums can add up but you can save money by getting a CityPass if you plan to go to more than one (includes 4 attractions including the aquarium and Museum of Science. Gbcvb.citypass.com).
Ride public transportation in Boston with the T or water ferry
Boston has a cool transit system that ranges from above-ground trolleys to water ferries. If you have a little boy who is into trains and boats, this is a cheap option to see different parts of Boston in a fun way!
Eat Boston Cream Pie at the Omni Parker House Hotel
The Omni Parker House Hotel downtown is a historic hotel that has been around for 100 years! It was mentioned during our Freedom Trail tour for its historical significance (it was also featured on a Nighttime Ghost Tour I went on many years ago! Supposedly certain floors are haunted.).
The lower level where the gym is located has its history lined up in the hallway of old newspaper articles, a timeline of events, and profiles of famous people who have worked or stayed there over the past century.
The kitchen at the Omni Parker House Hotel is also the place where the Boston Cream Pie was invented. In place of dinner, grab a slice to share with your family. You’ll get a piece of history in each delicious bite, especially if you eat it at the hotel!
Rent bikes and ride around the Back Bay
The Back Bay is one of the most gorgeous areas of Boston and perfect for a bike ride. I absolutely loved riding my bike along the paths here.
Blue bikes are the city’s bike rental service, and you can find stations all over the city. The blue bikes are mostly bigger so it’s a better option for older children.
Go on the Boston Duck Tours
The ubiquitous amphibious vehicle will be seen numerous times while you are in downtown Boston. Although it’s cringy to be seen on the gigantic boat on wheels, it’s really fun for the kids. The adults will get a tour of the city and lots of interesting facts. The kids enjoy going into the water and will even have a chance to steer the boat.
To alleviate the cringiness of the tour, skip the “quacking”. 🙂
Quincy Market for a bite to eat
Quincy Market and Faneuil Hall are stops along the Freedom Trail but it’s also a popular tourist stop worthy of an afternoon. There are many options for food, including Boston staples such as clam chowder, baked beans, and raw oysters.
Faneuil Hall was an old market building built in 1742, and the second floor was the site of many town meetings where Sam Adams and others lead cries of protest against taxes imposed on the colonies.
Outside of Quincy Market, you can often see free live performances ranging from live music with a variety of different musical instruments to stunt performers.
Visit Chinatown for cheap eats
The Chinese friendship gate welcoming you into Chinatown is located a short walk from downtown. Visit Chinatown for a cheap bite to eat, such as the bakery, dim sum, noodles, and boba tea.
It’s also interesting to note that Boston’s mayor is Chinese. Her picture is featured prominently in a mural in Chinatown.
Walk around the North End (Little Italy)
The North End, or LIttle Italy, is a cute area north of downtown that has Italian restaurants, pizza joints, and specialty food shops. Walking through the narrow streets is almost like walking in Rome. You can find shops selling bread, Italian cookies, and other goods.
A few historical sights are worth checking out here, including Paul Revere’s house, Paul Revere’s statue, and the narrowest house.
Visit a college campus
If you have older kids (12+) who are thinking about college already, then why not check out the many colleges and universities offered in Boston? That is how many young adults (including me) land in Boston!
There are many campuses to check out for prodigious children who already know they want to pursue higher education. Harvard University, Berklee College of Music, MIT, Boston University, Boston College, Northeastern University to name a few. Some campuses are prettier than others so if you’re kids are not thinking about college yet, then Harvard University is the ideal (and any Asian parent’s dream!).
Where to stay in Boston
Boston is expensive and it’s hard to stay somewhere centrally located without shelling out a few hundred bucks a night for accommodations. If you’re visiting Boston for the first time and want to be conveniently located to most of the major sights, then you’ll want to stay:
We stayed at the Omni Parker House Hotel, which was very convenient to the major sights. We also enjoyed being in the historic hotel and it was one of the cheapest that we could find. However, the rooms were small and there wasn’t a pool or hot tub for the kids (not that we had enough time to go into those since we were too busy sightseeing).
The newest development in Boston, this area has become the center for conventions, (houses the Boston Convention Center), entertainment, outdoor areas for gatherings, as well as restaurants, museums, galleries, and shops. New hotels can be found here most with new amenities suitable for families, such as swimming pools, hot tubs,
The further out you go from Boston, the less expensive the accommodations will be. This may be worth it if you plan to be at the hotel for extended periods of time (if you have toddlers or younger kids that can’t walk much and need naps). Check out areas that are easily accessible by T to the major sights and has its own unique vibe, including the Back Bay, Brookline, and Dorchester.
Day trips from Boston
Although Boston and Cambridge have enough activities to keep your family busy for several days, consider a day trip if:
– Your family is visiting from overseas (or another far off location – even the west coast of the U.S.A.!) and don’t anticipate going back to New England anytime soon;
– You are wanting to get out of the city for a day;
– It’s not your first visit to Boston and you’ve hit all the major attractions on previous visits
– One of these day trips from Boston really entices you! Boston has many options for day trips. Some ideas include:
Whale watching tour
Gloucester, MA is the starting point for whale watching tours with several tour companies offering boat rides out into the ocean to see whales. The best time to go is from May to October, with the best month being September.
If you crave the beach and want some relaxing time away from the hustle and bustle of the city, hit up Cape Cod. There are plenty of strips of beaches to choose from all along the cape. The tip of Cape Cod is Provincetown, the LGBQT-friendly seaside haven offering galleries, specialty shops, cabarets, and restaurants/bars. You can take a ferry to Provincetown from Boston.
Famous for the Kennedy’s home place, Martha’s Vineyard is a taste of history in a relaxing, beautiful island.
if you are interested in witches or a bit of dark history, check out Salem! October is the best time to visit, but you can go at all times of the year to check out the Witch Museum, psychic readings, and magic shops.
Old Sturbridge Village
A re-creation of an 1830s settlement, Sturbridge Village is a unique experience for families and for kids to see how life was in the olden days (when everything had to be done by hand). This place offers costumed staff, carriage rides, and blacksmiths, as well as a pottery kiln and sawmill.
Boston and the surrounding area makes a fantastic family vacation. There is a good reason that this is one of my favorite cities in the United States, and maybe even the world! The history makes a fascinating backdrop, and all the sights, food, culture, and things to do makes Boston at the top of my list.
Are you adding Boston as a family vacation destination in the near future?
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