Are you considering Boston as a destination for a family vacation in the near future? Great choice! Steeped in American history, Boston is also rich in culture, diversity, unique sights, and fascinating stories.
Not only is Boston interesting and fun, but it’s beautiful! The capital of Massachusetts is situated right on the harbor and has a lovely skyline. Boston also has a river, plenty of green spaces in the form of parks and squares, and gorgeous historic brownstones.
Boston has a lot to offer for any family looking for an unforgettable vacation. I highly recommend that you visit when the kids are old enough to learn and appreciate its history. Summer is also the best time to experience Boston.
Boston will always hold a place in my heart. I lived there for a few years in my early 20’s and have many fond memories of “Beantown”.
This year, I had the chance to visit again for the first time in many years. So much has changed but the things that I loved about Boston are still there.
Here are my Top 5 recommendations for sights and things to do that are unique to Boston!
1. Walk the Freedom Trail and Black Heritage Trail with a costumed tour guide
The Freedom Trail, a 2.5-mile red brick trail lining the middle of the sidewalk, takes you to various spots in downtown Boston of historical significance.
Almost every guidebook will recommend the Freedom Trail when you visit Boston and there’s good reason. It’s one of the must-do’s to learn about everything that happened from the time the Plymouth sailed across the ocean to the fight for freedom from the British monarchy.
Many monumental events that defined the formation of the U.S. took place in Boston. You can learn about these through fascinating stories at the stops along 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 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
- 54th Regiment Memorial. This impressive bronze piece lies across from the new 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).
- Old Granary Burial Ground. Famous cemetery with graves of Paul Revere, John Hancock, Samuel Adams, and other important figures. Interesting stories of this cemetery are told during the walking tours.
- Old Corner Bookstore. Now a Chipotle, this original building was built in 1718 as an apothecary and became a literary center for famous authors to publish their manuscripts.
Although you can grab a map and walk the trails on your own, I recommend a walking tour with a tour guide. The experience is even better when the guide is in full costume (ours was dressed as Mother Goose)! Walking the Freedom Trail and Black Heritage Trail is more entertaining with a guide and will keep kids engaged with interesting stories and facts about the sites and key historical figures.
Although there are free walking tours available, 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 everything that has taken place there.
2. Attend one of Boston’s special events or a cultural festival
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 is loud and proud about its city and it really shows during a special occasion. 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.
There’s no better way to experience the vibrant culture 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.
3. Watch a 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 just 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”!
4. 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!
5. 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 original clam bar is a fixture on the waterfront. Landmark in the historic Fort Point Channel, a gateway to the Seaport District. A memorable meal under a tent lined with picnic tables, you can have a lobster rolls, fried clams, steamers, mussels, and crab cakes.
- 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
6. 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.
7. Ride the Swan Boat 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.
8. 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.
9. 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.
10. Kayak along the Charles River between Boston and Cambridge
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).
11. 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.
12. 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.
13. 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.
14. 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
Suitable 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, the building is reminiscent of a 15th century Venetian palace. Also, a daring art theft happened here in 1990 – you can read more about it here.
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).
19. 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!
20. 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!
21. 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.
22. Go on a Duck Tour
The ubiquitous amphibious vehicle will be seen (and heard) 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”. 🙂
23. 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 area worthy of a couple of hours. Quincy Market has many options for food, including Boston staples such as clam chowder, baked beans, and raw oysters. My kids love the New England clam chowder served in a bread bowl.
Faneuil Hall was an old market building built in 1742. The second floor was the site of many town meetings where Sam Adams and others protested 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.
24. 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.
25. 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.
26. Visit the Mapparium at the Mary Baker Eddy library
Here at the Worldly Girl Guide, I highly recommend visiting any place that gives you a glimpse of the world! At the Mary Baker Eddy Library, the Christian Science Library located in the Back Bay near the Symphony T line, there is an exhibit called “How Do You See the World?”. This interactive experience has several exhibits including its iconic Mapparium globe room. The stained glass globe room is awe-inspiring and the building itself is in a 1930s neoclassical building.
We did not have a chance to visit during our 5-day stay last summer, but we will put this on the list for our next visit!
27. 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:
Downtown Boston
Omni Parker House Hotel ended up being the cheapest choice downtown, so we ended up staying there. The historic hotel is very convenient to the major sights. 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). However, my husband and I liked the historic aspect of the hotel.
Seaport District
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 and 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.
Cape Cod
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.
Martha’s Vineyard
Famous for the Kennedy’s home place, Martha’s Vineyard is a taste of history in a relaxing and beautiful island.
Salem, Massachusetts
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 like in the olden days. This attraction has costumed staff who will play the part in pretending that they are living in the 19th century when everything had to be done by hand. You can observe the blacksmiths working, as well as the pottery kilns and sawmills operating. Carriage rides are available.
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