With Kids! 
“Every city looks the same.” That’s what they say of U.S. cities. The big hole in that theory is really old cities: like Boston.
We fell in love with accessible Boston because its old city charm is alive and thriving, even as it’s full of hip new stores, culinary delights, and endless play options.
The historic landmarks of the city are close enough together that you can cover the major highlights in a short trip, or take your time to discover both old and new over a longer stay.
When to Go
“I’ve never been to Boston in the fall!” Anyone else singing?? This is an unfortunate truth for both the pirates who don’t do anything and myself. Apparently that’s the best time – for weather, for crowds, and for foliage.
Boston is also far enough north that summer temps aren’t usually miserable (though it did hit 94 degrees while we were there). Summer also brings crowds – especially on weekends. We visited during the week, in July, and crowds were minimal.
Getting Around
Boston has a mostly accessible public transportation system. A lot of people find it easier to park outside the city and take public transportation. If you’re staying in town, your hotel could be charging as much as $40 per night to park, so you may want to consider ditching your car and sticking with the bus. You can find cheap parking outside the city here.
Since we stayed outside the city, our hotel parking was free. Parking in any metered space in Massachusetts is free with a handicap placard, so we opted to drive in and park. We were able to find handicap parking near most of our destinations. When we couldn’t, we put the placard up and claimed a regular metered space (still free).
There is no public parking in North End.
What to Do
Boston is full of history and contemporary fun. While I’m a big fan of both, if you’re short on time you should focus on the stories behind our freedom.
The Freedom Trail
The Freedom Trail is a 2.5 mile brick-marked trail that connects each of the historic sites. While the highlights of the trail are a must, I don’t actually recommend walking it in its entirety. Parts of the trail are uneven, and you’d need to take small detours at parts to avoid steps. You can see most of these stops from an Old Town Trolley tour.
Paul Revere’s House
Paul Revere is probably the first historic figure that comes to mind when you think of Boston… even if he never really shouted “The British are coming!” As the home of the midnight rider who called the rebels to action, it’s a neat place to see and holds a lot of history. We thought the house was still closed because of Covid, but apparently it’s just closed on Tuesdays. Oops! We enjoyed what we were able to see from outside and from the gift shop, so please let me know how the rest of the tour is, ok?
Oh, also, the Paul Revere House is now fully accessible!
Boston Tea Party Ship
If you only do one thing with your time in Boston, this should be the thing. The tour guides managed to show the weight and significance of Boston’s role in the Revolutionary War, while keeping it light, engaging, and appropriate for kids. Don’t even ask me how. It was impressive.
We learned a lot, we threw tea overboard, and we left feeling patriotic. What more could you want??
Only one of the ships is wheelchair accessible, which means your tour runs every 30 minutes instead of 15. We weren’t able to go below deck, but the bulk of the tour takes place on the main deck. If you really want to see what the lower deck looks like, there is video available, but I don’t think we’re missing much.
Boston Common and Public Garden
The Boston Common is where you can see the famous “Make Way for Ducklings” sculpture, based off of the book. It’s also where you can ride the Swan Boats that have been in operation since 1877 – always under the same family (the Swan Boats do require you to transfer from your wheelchair). It’s the nation’s first public park and public garden. It’s like the Central Park of Boston and it’s a great place to unwind and enjoy the scenery.
Faneuil Hall
It was a marketplace then, and it’s a market place now. Faneuil Hall is a unique opportunity to see where the earliest conversations on our freedom took place… and to indulge in some tasty treats. It’s a neat place to take a walking tour and soak in the history… or to grab some lunch.
USS Constitution
The USS Constitution is the oldest commissioned ship in the United States Navy, and is still used for service. The boat is historic and has extremely limited accessibility. We didn’t go in, but it’s still neat to go look at. Admission is by donation, so there’s no loss to just do a roll-by. While you’re out there, you can visit the neighboring USS Constitution Museum.
USS Constitution Museum
This is the wheelchair accessible way to experience the history of the USS Constitution. The USS Constitution Museum has interactive exhibits to walk you through every part of the ship’s history – from building, to battle, to the people that have served on board. The kids enjoyed playing a different kind of battle ship and pulling up the rigging.
Admission is by donation and the facility is wheelchair friendly.
Boston Children’s Museum
I’m all about doing things unique to the city you’re in, so I don’t usually include children’s museums or science factories. That said, the Boston Children’s Museum is right on the waterfront, in the center of all the action, it’s $2 with your disability ACCESS card, and the kids had an absolute blast. In fact, if you don’t want to go in, they’re also running free outdoor programs right in front of the museum. My kids spent two hours building their own mini-golf course out of recycling… after we paid for the inside portion of the museum. Check out this calendar of fun things to do without even going in!
The museum was easily accessible (minus the one climbing structure that descends the height of the building).
All Abilities Play
We’re always on the lookout for good playgrounds when we travel. Boston had playgrounds around every corner, and they actually have several wheelchair accessible playgrounds and splashpads. The Shipyard Playground is right by the water and near all the action.
Old Town Trolley
The above were some of our favorite accessible Boston highlights, but there’s a lot to cover! We started our trip with an Old Town Trolley tour to get an overview of the city and decide what we wanted to spend more time on. That’s right, we did 0 planning ahead of time and put the fate of our entire trip in the hands of Old Town Trolley (with some bonus tips for meals and kid-activities from GoWhee). We had already done their tours in both Nashville and St. Augustine, so we knew we could trust them for both accessibility and a brilliant tour.
The tour includes a map of stops and city highlights. That makes it easy to plan your trip while you tour. The hop-on/hop-off capability makes it easy to spend time in the places you want to, and do the drive-by tour for the things that don’t require you to get out and wander. We booked for two days this time, so that we could use Day 1 for an overview and some quick stops, and use Day 2 for basic transportation to the areas that had captured our attention.
Anything that I missed in my city highlights above is included in the tour. If you know when you plan to start the tour, I suggest calling in advance (617-269-7150) so they can have an accessible trolley ready for you. Not all of the trolleys have wheelchair lifts, but they can be pretty accommodating with scheduling, as long as you communicate – even with hop-on/hop-off capabilities.
Where to Eat
Oh. My. Word. Who knew Boston was a foodie paradise? Even if I had seen enough of the city, I’d be planning a return visit just for the food.
North End
This is Little Italy and the place for all things Italian – it’s a destination of its own. While there are gems in all of the alleys and backstreets, start with Hanover Street to get a feel for the area and what’s available.
Mike’s Pastry
Mike’s Pastry is a North End tradition with Mike’s one of a kind cannoli. Not a cannoli fan? I’ll be nice and not ask what’s wrong with you, also let you know that there are plenty of other home-made pastries to meet your needs.
Ristorante Saraceno
I’ve visited 34 countries and countless restaurants, and this little place in Boston is the best restaurant experience I’ve ever had (NOT a hosted visit – we just loved it that much!). Ristorante Saraceno has deliciously authentic Italian food, great lunch specials, and the kind of service that will make you think you’re visiting family in Italy. They specially made meals for my kids’ weird requests, taught them how to twirl their pasta, and helped them tuck their napkins into their shirts.
We tried a couple of dishes to share, and they were all phenomenal.
The restrooms are a little tricky because of the doors, but the restaurant itself is easily accessible.
Flour Bakery
Flour Bakery is a Boston chain with baked goods, coffee drinks, and basic café items. Good for breakfast, lunch, or a pick-me-up any time. Nothing here is not delicious. And they didn’t throw us out when we broke their giant flower pot…
Friendly Toast
With menu items like “Thick cut English muffin, Local NH North Country smoked ham, rice crispy coated chicken breast, VT cheddar cheese sauce, poached eggs, Hollandaise & Sriracha glaze,” you can see why The Friendly Toast made my list.
Endless Yum
We didn’t have time to eat it all, but you should make food a priority in this city. There’s also a Bartaco right behind the children’s museum. Yankee Lobster, a short walk from all the action, made an excellent choice for local seafood. GoWhee had a kid-friendly jazz bar listed, but we didn’t have time to check it out.
Where to Stay
Boston is a big city with all of your favorite chains. We didn’t find any unique options with wheelchair accessibility. There are some wheelchair accessible HomeExchange options, but we weren’t able to make any work with our availability.
We typically travel on points, so we chose to stay outside of the city to double our value. I will advise you that the Fairfied Inn Boston Dedham is not worth the points. It’s old, the rooms are tiny, and the staff are overworked. The Four Points by Sheraton Norwood, just down the road, however, was spectacular. The rooms were spacious, the staff was accommodating, the facilities were beautiful, and the pool was just what we needed to unwind at the end of the day.
That being said, there are also several options in the center of the city!
In summary, eat, play, throw tea, and take the trolley! You won’t be sorry!