Heading to Boston soon? Your family is in for a real treat! There are so many things to do in Boston perfect for a family vacation. Boston is one of my favorite cities in the United States and places I’ve lived in the world.
With this 5-day Boston itinerary, you’ll have the perfect amount of time to get a feel of the city, and explore its beauty, cultural diversity, and history!
Located right on the harbor, Boston has a plenty of water in the form of the Atlantic Ocean and the Charles River (we are always seeking water on our vacation as Arizona desert dwellers!).
In addition, Boston has plenty of green spaces in the form of parks and squares, and gorgeous historic brownstones. In my opinion, Boston is one of the most beautiful cities in the United States!
Boston is a walkable city, with many sights clustered together close to the downtown area. The capital of Massachusetts has more of a neighborhood feel, but is rich in interesting history, variety of culture, warm and welcoming people, unique sights, and fascinating stories.
Boston is a great destination for families. I highly recommend that you visit when the kids are just old enough to learn and appreciate the history. It would be even better if they are learning American History at school. The 5-day itinerary will reinforce their history lessons!
“Beantown” will always have a special place in my heart. I had lived in Boston in my college and post-college years and have many good memories of my time there. When I visited for the first time in many years with my family last summer, it brought me joy and life. Even now, I miss the city and thinking about when I can go back. Not many cities in the world have this kind of pull on me!
How do you get around Boston?
Boston is best explored by foot, especially in the downtown area where the streets are a big jumbled mess. It is said that the streets were originally cow paths, which explains why they are the way they are (just take a peek at a map of the downtown area to see what I mean)!
Driving is not recommended unless you plan to leave the city for day trips. If it’s your family’s first time and want to explore the historical sights, then it’s best to stick to walking. Other options for exploring outside the downtown area include taking public transportation (the T), renting bikes through the bike sharing program Blue Bikes, or ride sharing apps like Lyft and Uber.
Day 1: Walk the Freedom Trail, stop at Faneuil Hall & Quincy Market, visit the U.S.S. Constitution, and go to the North End (Little Italy) for local eats
You cannot visit Boston without learning about its history and the city’s role in the founding of the United States. Many pivotal events happened in Revolutionary Boston in the 1700s, including the Boston Tea Party, the Boston Massacre, the famous ride by Paul Revere, and the Battle of Bunker Hill.
To start off your 1st full day in Boston, get your walking shoes ready and be prepared for full-on history lessons, key sights in the American Revolution, and local eats!
Have a quick breakfast at Bakey, a European/Israeli bakery selling babkas, burekas, and other baked goods.
Next, cross the street to the Boston Common visitors center, where you can shop for gifts and buy tickets for the next
Guided walking tour of the Freedom Trail.
You can also buy tickets ahead of time here. Make sure the tour guide is costumed, especially if you have kids with you. It’s a great way to lend some fun and imagination to history, get the kids more engaged, and bring you back to that time period.
The Freedom Trail guided tour will take you through Boston Common and along a red brick trail around the downtown area. Stops include:
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.
Omni Parker House Hotel. This historic hotel across from the Old Granary Burial Ground has been around since 1855 and is where the Boston Creme Pie was invented. Many famous people stayed here (and Malcolm X worked in the kitchen). It’s also one of the focal points of the fun Boston ghost tour.
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 apothecary and became a literary center for famous authors to publish their manuscripts.
The walking tour ends near Faneuil Hall.
Visit Faneuil Hall and Quincy Market
This is a good spot to spend a couple of hours, grab a bite to eat, and learn more history before continuing on the Freedom Trail.
You can continue the history lesson by visiting the second floor of Fanieul Hall. Town meetings led by Samuel Adams were held here between 1764 to 1774 to protest taxes imposed on the colonies by the British. Later on, this became an important meeting place for African Americans in their fight for freedom, with Frederick Douglass and William Lloyd Garrison speaking here.
Take a stroll through Quincy Market, the famous marketplace for all sorts of eats.
Walk down the aisles to find various food and gift vendors. You’ll find delicious goodies that you’ve been craving, from clam chowder, sandwiches, ice cream, lobster rolls, pizza, and a lot more.
If you want a sit-down place to eat, head over to the Union Oyster House, the oldest restaurant in America, to immerse yourself in the history of Boston.
After lunch, skip over the Freedom Trail that goes through the North End (you’ll come back here for dinner) and continue on the Freedom Trail by taking an Uber or walking across the bridge from Fanieul Hall to
Visit the Bunker Hill Monument.
The tall obelisk commemorates one of the first important revolutionary battles that took place there – the Battle of Bunker Hill. An audio tour takes you around the obelisk to tells the story of how the community, including blacks living in the neighborhood, rallied together to fight the British. Ultimately the British won this battle, but they faced heavy losses and instigated more military action against the colonists.
To learn more about the history, you can visit the museum across the street. You can also climb up the stairs in the obelisk and get views of the surrounding area (it was closed for maintenance when we visited).
Next, head to the Charlestown Navy Yard to see the
U.S.S. Constitution Battleship and Museum
“Old Ironsides” is the oldest commissioned warship afloat in the world. Walk around the ship and go below deck to check out the cannons. To check out more ships, head to the USS Cassin Young.
After looking around the ships, check out the U.S.S. Constitution museum. This is a fantastic interactive museum and tells the story of life on the ship, how the U.S.S. Constitution was made, and its historical significance. Kids will love the hands-on exhibits, and surprisingly I learned a lot and thoroughly enjoyed this museum!
Head back to the North End (Little Italy) for more of the Freedom Trail and an authentic Italian dinner
There’s still some more sights on the Freedom Trail to see in the North End, including the Paul Revere House and Copp’s Hill Burying Ground.
You can also view the narrowest house and Paul Revere Square. After visiting these sites, pick a place to eat for an authentic Italian meal in Little Italy. There are several choices on Hanover and Salem Streets. Pick one that looks good and is in your price range!
After dinner, walk around LIttle Italy to the small shops selling bread, cookies, and other Italian delicacies.
Buy some bread and spread for tomorrow morning’s breakfast. For a sweet treat:
Grab a cannoli at a bakery in the North End
You and your family have done a ton of walking today, so reward yourself with a cannoli! This famous Italian dessert with a creamy cheese-filled center surrounded by a crispy cover is found all over the North End.
The most famous place to grab a cannoli is at Mike’s Pastry. At Modern Pastry, you can build your own cannoli. Bova’s bakery is a place where you can get a cannoli and baked goods for tomorrow morning’s breakfast!
It has been a long day! Go back to your hotel to relax in the pool or hot tub or rest up at your Airbnb. You have more walking to go tomorrow!
Day 2: Black Heritage Trail, Acorn Street, Boston Common and Boston Public Garden
Continue the U.S. history lessons on the Black Heritage Trail. This 1.6-mile trail around the Beacon Hill neighborhood showcases the homes, businesses, schools, and churches of African-Americans during the formation of the United States. Black Bostonians were free from slavery, yet they still struggled for equality and freedom during a time that America’s early documents promised liberty.
The first stop is the stunning 54th Regiment Memorial on the corner of Park and Beacon Street.
Located across from the gold-topped new Massachusetts State House, this impressive bronze memorial depicts the first black regiment that fought in the Civil War.
The National Park Service offers tours, and it’s best to hear from a park ranger/tour guide the story of Col. Robert Gould Shaw, the 54th Regiment, and the artist Augustus Saint-Gaudens.
Other stops on the Black Heritage Trail include the Abie School and the African Meeting House.
While you are in this area of Beacon Hill, admire the amazing brownstones and imagine all the history that took place in this neighborhood. Next,
Take photos on Acorn Street
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!
Stop in Cheers for refreshments and nostalgia
If you are in need of a drink, bar food, and a dose of 80s nostalgia, stop in Cheers. This place is pretty touristy, but it’s also family-friendly and fun for people who grew up watching the show on an actual television!
Walk through the Boston Common & the Boston Public Garden
It’s time to enjoy these historic and beautiful parks right in the middle of the Boston. These two parks have it all – history, tall trees, green grass, a pond, walking bridge, and wildlife (birds and squirrels). Definitely take a couple of hours to walk around both parks, sit on the benches and enjoy watching the swan boats.
Start off at the Public Garden, America’s oldest botanical garden, where you can cross the bridge and admire the George Washington statue, Make Way for Ducklings bronze statues (based on the popular children’s book) and the bench during the scene in “Good Will Hunting” where Robin Williams’ character gives Will an earful about life.
If you have small children, then go on the
Swan Boat Ride
The non-mechanized boats has been running as a family business since 1877. It’s a calming and soothing ride and a Boston tradition that takes you back to an era of the early days of Boston.
Head to the Boston Commons, the bigger park of the two, so that the kids can play in the Frog Pond (used as a splash pad in the summer and ice skating rink in the winter) and the nearby playground.
After spending some time in the parks, head east toward Downtown Crossing to
Browse the Brattle Book Shop
Boston has a few historic bookstores and Brattle Book Shop is one that everyone in your family can enjoy. As the largest and oldest used bookstore in the United States, all sort of books and gifts are sold for discounted prices.
Have a bite to eat in Chinatown
A few blocks away from the Brattle Book Shop is the Chinese friendship gate, welcoming you into Boston’s Chinatown. Here you can get some cheap eats, herbs, fun trinkets, and delicious baked goods.
Stop in the Bao Bao bakery and cafe for coffee and dessert. You’ll find all sorts of goodies here such as pineapple buns, matcha roll cake, macaroons, and ube desserts. Grab some goodies for breakfast tomorrow.
Did you know that Boston’s mayor is Chinese? Her picture is featured prominently in Chinatown, as well as other colorful murals.
See a show in the Theatre District
It’s time to wind down the busy day. You can see a show in the nearby Theatre District close to downtown and Chinatown.
Day 3: Museum Day, enjoy the water, seafood, and the Seaport District
Boston has many first-rate museums that are great for kids and families alike! At least one museum should be on your itinerary during your vacation, especially with kids.
There are 3 different options for your itinerary depending on what your family wants to see.
Option A: New England Aquarium & Boston City Harbor Cruise
The aquarium features a giant glass tank with a multi-level walkway. The highlight are the penguins, in which you can spend hours watching their antics. The aquarium also has seals and sea lions.
Right next door to the aquarium is where the Boston Harbor City cruise departs from.
Option B: Museum of Science and Duck Tour
The Museum of Science is a massive structure housing several interactive exhibits that will keep your family entertained for hours. A T-Rex stands out front for dinosaur fans, plus the museum has an IMAX theatre and is connected to the planetarium.
The Boston Duck Tour departs in front of the Museum of Science, so you can conveniently hop onboard the amphibious vehicle that goes around the downtown Boston area and then goes into the water either at the Charles River or the bay.
Option C: Children’s Museum & Boston Tea Party Ships & Museum
These two smaller museums can be done together, starting with the education/history museum first.
At the Boston Tea Party Ship and Museum, character actors reenact the events leading up to the Boston Tea Party. The highlight for most kids is throwing fake tea over in the same body of water where the Boston Tea Party took place in 1773.
After spending an hour at the Boston Tea Party museum, walk across the bridge to the Children’s Museum. This museum for children 10 years and under offers 4 floors and several rooms of interactive and hands-on play. Kids can do arts and crafts, play in a ball pit, climb obstacles, and much more.
If you want to go to multiple museums, get a CityPass and T pass to save some money.
After the museum, it’s time for more seafood. The aquarium, Children’s Museum, and Boston Tea Party museum are all close to:
The Barking Crab restaurant
This place has been here for decades, and offers open-air seafood dining right on the harbor. It can be a tourist trap (i.e. overpriced), but it’s fun, has a great ambiance, and offers all sorts of mouthwatering seafood. You can get lobster rolls, lobster mac n’ cheese, steamers, oysters, clam chowder, fried clams, etc. Washed down by a refreshing Sam Adams beer, the experience can’t be beat and will be one of your more memorable meals in Boston!
If you didn’t ride a boat after the museum, it’s time to do it now. There are many options between the Boston Duck Tour, Boston Harbor City cruise, a water taxi, or the MBTA public transportation ferry. https://www.mbta.com/guides/ferry-guide#
Explore the Seaport District Harborside
The newest development in Boston, this area was not around when I lived here! But what was formerly an industrial dead zone has morphed into the premier entertainment district with hotels, restaurants, parks, the Institute of Contemporary Art and live entertainment.
The kids will enjoy the light up swings at the Lawn on D. You can also play ping pong and bocce ball while you relax on the grounds.
If you want to continue the day with more activities, then go on a ghost tour. Ghost tours are offered as walking tours or on a trolley. But first,
Eat Boston Cream Pie at the Omni Parker House Hotel
The hotel kitchen is the place where the Boston Cream Pie was invented. Eat a slice of pie at the hotel before the ghost tour starts!
Day 4: Culture and Activity Day: Rent bikes and ride along the Esplanade by the Charles River, Back Bay Area, Isabella Gardner museum, Copley Square
This day will be spent seeing the beauty and diversity of Boston. Start by
Renting blue bikes, the public sharing bike service with stations around Boston.
Ride along the Esplanade and path to see the Charles River.
Next, head over to the Back Bay area. This used to be my favorite place to ride bikes.
Ride along the trails along the Back Bay Fens
This park has a bike and walking path that goes along the river way. It’s a scenic area of Boston with beautiful flora, ponds, bridges, and greenery. The highlight of the park are the Victory Gardens, Rose Gardens, community gardens and war memorials. They also have playgrounds and ball fields.
Park your bike at the stop and visit the Isabella Stewart Gardner Museum – one of the most unique and beautiful art museums in U.S.. Aside from the Italian Renaissance art, the building is reminiscent of a Venetian palace with an amazing courtyard. I recommend the audio tour from your phone, where you can hear the story of the daring theft in 1990 when 13 paintings were stolen.
You’ve worked up an appetite, so grab a bite to eat at the many restaurants in the area, from pho to shawarma to more seafood.
If you want to see more art:
head to the Museum of Fine Arts.
stop in the Mary Baker Eddy Library to check out the stained glass globe room.
Walk toward Copley Square where you can see the impressive Trinity Church with its high ceilings and beautiful stained glass.
The Boston Public Library, the first municipal library in the U.S.
Established in 1848, the Boston Public Library in Copley Square is huge with beautiful architecture. There are art and architecture tours offered for free in the library.
Walk down Newbury Street to window shop the various boutiques and fancy restaurants.
Time to take a food tour through Live Like a Local.
This black-owned tour company highlights neighborhoods and businesses of color. The tour features food and drink from Roxbury’s Nubian Square, Dorchester’s Uham’s corner (Cape Verdean community), and Jamaica Plain’s Hyde Square (Latin Quarter). You will sample cuisine from Jamaica, Trinidad, Nigeria, Cape Verde, and Cuba.
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 summertime.
Examples include the Caribbean American Heritage Festival, Portuguese Festival, Ukrainian Festival, Hong Kong Dragon Boat Festival, African Festival, Puerto Rican Festival, and so much more. Ask your tour guide which festivals are offered during your vacation.
Day 5: Cambridge, Charles River
It’s time to cross the bridge to the other side of the Charles River into Cambridge. Ride the T on the red line to Harvard Square and Central Square to get an eclectic and diverse vibe. Eat at the Veggie Galaxy, a vegetarian diner with an old-style diner feel and funky decor.
Check out Harvard University
Some parents may take their kids to visit Harvard University to live out their dream, but in reality the campus is beautiful. As the oldest university in the United States, it has a lovely campus with green grass, enormous leafy trees and brick buildings.
While you are here, check out the statue of John Harvard (touch the feet for good luck) and practice your Boston accent (by saying “I pahked my cah in Hah-vahd Yahd”).
A free tour of the Harvard University campus is available by college students themselves. After the tour, head into
Harvard University’s Museum of Natural History
This is a good museum to take kids to explore animals, gems, insects, and more.
After touring the Harvard University campus, check out Harvard Square for its quirky shops and ethnic eats. Highlights for shopping are Newbury Comics for records and gifts and the Harvard University bookstore.
Cambridge is home to many international people, so here you will find food from around the world. Ramen joints, Vietnamese, Mediterranean, Indian, Mexican, and Venezuelan cuisine can all be found near Harvard Square.
Kayaking along the Charles River
It’s time to spend some more time IN the Charles River, by doing some kayaking. Cross over the Charles River to get to the Allston/Brighton area to do some kayaking or canoeing at https://paddleboston.com/. They have paddle boarding, kayaking, canoeing, and more activities on the Charles River. They also have other locations around Boston.
Grab some Korean food in Allston along Harvard Avenue
My old neighborhood formerly made up of bars, clubs, and casual eats has morphed into a mini Koreatown over the past several years. After working up an appetite from kayaking, stroll along this area to sample Korean cuisine. Everything from black bean noodles (ja-jang-myun), to spicy rice cakes to Korean fried chicken, to oxtail soup and soft tofu stew can be found in this area. You can also get boba tea, mochi donuts, and shaved ice desserts along this strip.
Ride the green line T into Kenmore Square to:
Watch a Boston Red Sox baseball game in Fenway Park
For your last night in Boston, your family definitely need to go to Fenway Park to watch a Red Sox baseball game. Even if you don’t particularly enjoy baseball, being in the stadium (oldest baseball stadium in the country) and feeling the Boston vibes.
There’s no better way to end the day or spend a summer evening than sitting in the ballpark with a view of the Citgo sign and watching baseball. Get ready to stand up for the wave and the sing-a-long to “Sweet Caroline”!
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 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.
Hope you and your family love Boston as much as I do! This itinerary packs a lot in, but there’s so much to see and do in this wonderfully historic and beautiful city.
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