There’s a specific moment that I always come back to when I think about our first trip to Boston.
My son had just turned one and we spent a fall afternoon wandering through the Public Garden. The weather was cool, it was a little overcast, and we were just back from an authentic Italian lunch in the North End.
It was in that moment that I realized what an incredible city Boston is for families. It’s exactly why I visited again when my son was four, and why I put together this 3-day Boston with kids itinerary.
On our second trip, we were really able to enjoy all that Boston has to offer (sans nap schedules). It’s a beautiful city with tons of history, amazing restaurants, and so much to do for families.
For both trips, we stayed for a long weekend. Three days is the sweet spot to hit Boston’s top attractions, enjoy a bowl of clam chowder or two, and still have time to let the kids run loose in the parks.
My 3-day Boston itinerary below is a blend of what we did on both of those trips.
I’m covering where we stayed, the can’t-miss stops like the Boston Children’s Museum and the New England Aquarium, the parks where my son ran off the most energy, and the restaurants we loved — including a few you’ll recognize from my Boston restaurant guide.
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Day 1
Check in at either The Bostonian or Fairmont Copley Plaza. Both hotels are great options for visiting Boston with kids. They’re in different neighborhoods and have different experiences depending on what you’re looking for.
After a long travel day with kids, a quick meal is always a good idea. Stop at Quincy Market for a quick lunch and Faneuil Hall to grab souvenirs.
Quincy Market is the largest and oldest food hall in the country, so you’ll get your first dose of history here!
More practically, there are tons of food options for the whole family (even picky eaters!). In my opinion, you need to welcome yourself to Boston with a bowl of chowda’!
Next, head to the waterfront and pick up the Old Town Trolley tour.
The Old Town Trolley is one of our favorite things to do on the first day of a Boston trip with kids. You get a lay of the land and can map out sites you may not have planned for.
It’s an especially good way to see the city with kids if you don’t want to hear them complain about getting tired or having to walk too far.
The Boston Old Town Trolley tour stops at iconic spots like Boston Common, Cheers Bar, The Freedom Trail, and other landmarks. Throughout the tour, your driver will share historical information about the city, and give local pro tips and recommendations in terms of dining and activities.
It’s a hop on-hop off tour, so my recommendation is to ride the entire tour through once (which takes about an hour and a half). Then, on your second loop, stop at the locations you have energy for on your first day and make a note for yourself to visit additional locations on a different day.
End the day with dinner at Joe’s Waterfront, which is a quick walk from stop 1 on the trolley tour.
Joe’s is a mid-range restaurant, it’s not too casual and it’s not too fancy. Their menu is filled with local and fresh ingredients, including seafood options. I’d recommend starting with the crispy Brussels sprouts for the sauce alone!
They also have a great kids menu with staples like chicken tenders and pasta, or more adventurous options like cheeseburger spring rolls. Kids meals come with a dessert sundae, which was a great motivator in getting my son to finish his food!
Maybe the best part of Joe’s is that it has an awesome view of Boston Harbor. If the weather is nice, I’d recommend sitting on the patio and timing your dinner to sunset. You won’t regret it!
And if your kids need to burn off some post-dinner energy, Christopher Columbus Playground is right across the street and a good pit stop before returning to your hotel.
Day 2
Head to the Fort Point/Seaport neighborhood and start your day at the Boston Children’s Museum.
The Boston Children’s Museum is a three-story STEAM-focused children’s museum with exhibits that range from space exploration to construction. There’s even a climbing gym in the entrance that goes all three floors up. Plan to spend AT LEAST two hours here, but I’d recommend a half day.
General admission tickets are $24 for ages 1 and up, but visiting on Sunday afternoons can be a great way to experience Boston with kids on a budget, as admission is just $1.
Read more about our experience at the Boston Children’s Museum.
Then, grab lunch at The Barking Crab. It’s a casual restaurant just a few minutes walk down the Fort Point Channel from the Boston Children’s Museum.
The Barking Crab is on Boston Harbor, so the views are great. It’s a very casual restaurant with a lively vibe, so kids fit right in.
If you like seafood, it’s a great restaurant to order a few apps for the table as your meal (get a margarita, too!). The ceviche was super flavorful, and you can’t go wrong with the hot crab dip.
They also offered a kids menu, and my hot dog-loving four-year-old was delighted that they serve two at a time.
After lunch, spend the afternoon exploring Boston Common and Boston Public Garden.
There’s tons of room at both for kids to run around and play. Boston Common has a playground and carousel, and summer splash pad/winter skating rink. And the Boston Public Garden is a great spot for a stroll and to admire some very well manicured gardens.
Cheers Bar is across the street from Boston Common, so pop in for an iconic photo (and a beer) while you’re in the area.
Finally, have dinner at Bell In Hand, which is America’s oldest tavern. It has been around since 1795!
Hundreds of years ago, it was a gathering place for everyone from sailors to politicians. The interior somehow still maintains that historical vibe!
Today, you can enjoy a fresh lobster roll in the same spot where some pretty famous people in history once dined.
Day 3
If you’re staying at the Fairmont Copley Plaza, grab a quick breakfast at Finagle a Bagel. They have incredible breakfast sandwiches (which just happen to be one of my favorite foods!).
If you’re staying at The Bostonian, grab breakfast at North 26 (the in-hotel restaurant). If you’re looking for something quicker, there’s a Starbucks in the North Market Building of Faneuil Hall. (Sorry, even in Boston I’m not a Dunkin girl.)
Then, before heading out of town, spend the morning at the New England Aquarium.
Highlights include stingray touch tanks right near the entrance, a massive penguin exhibit in the middle of the building and sea lion shows outside in the back by the harbor.
The New England Aquarium also has a giant ocean tank in the center. It holds 200,000 gallons of saltwater and the whole aquarium basically surrounds it! Make sure to visit the top to say hi to Myrtle the green sea turtle. They estimate she is between 70-90 years old!
And if the weather is nice and you’re not one to want your trip to end (like me), head to The Landing at Long Wharf. It’s close to the aquarium, and you can grab a final beverage before heading home. It’s my favorite way to end a few days of Boston travel with kids.
