A Boston city break with kids: family travel guide

Last updated: May 2026.

Boston was a big deal, being our ‘first’ of many with R: our first long-haul flight with a baby, our first time in the US together, and our first proper road trip as a family. And honestly, it’s been my favourite trip of the year so far for several reasons. Not only was it easy to visit Boston with kids, but the following the road trip was planned around R’s nap times and car journey tolerance levels, plus it also felt like a real adventure for us. I also loved travelling with R at this age (7-months-old), as it felt like we were witnessing it all through his eyes. And that felt pretty magical.

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Boston was the first stop on our road trip, and being as honest as I always am, it wasn’t my favourite US city. I expected to love it, and while it was compact, full of history, and a good mix of city landscape, water, and greenery, I wasn’t wowed by anything. And maybe that’s ok, especially as I loved some of the destinations that followed it (like Montreal, Vermont and Cape Cod). For context on this comment: last year I was wowed by Chicago’s architecture; I’ll never forget the country soul of Nashville; San Francisco was just so much fun; and who doesn’t love the bustle of New York? Boston was lovely but just felt a bit… forgettable.

Things to do in Boston with kids: quick overview

• Best activities: Freedom Trail walk (free, 2.5 miles), Harvard campus, Charles River Esplanade, Fenway Park
• Best for babies (0-12m): Outdoors activities, Boston Common, food halls (easy feeding)
• Best for toddlers (1-3): Boston Aquarium, Duck Tours, Boston Children’s Museum
• Best for older kids (4+): Freedom Trail, USS Constitution, Museum of Science
• Day trips: Salem (witches), Cape Cod (beaches), Vermont (mountains)
• Getting around: Very pram-friendly, compact city, good subway (some stations lack lifts)

Here’s how our family-friendly Boston itinerary played out:

We landed in the early evening, so we didn’t do much after checking into our Airbnb and grabbing some groceries, as it was already dark. R was suitably tired from a long day of travelling (it was well into the night by UK time), so we followed his usual bedtime routine and were pleasantly surprised that he slept through to 5:30am Boston time – I’m sure in part due to my jet lag strategy that I followed the week before we flew.

Things to do in Boston with kids: day 1 – Freedom Trail and Harvard

After an early start and a relatively chilled first wake window, we headed straight for Boston Common on the subway (see this handy subway map) and began the famous Freedom Trail. At 2.5 miles end to end, the whole route can feel ambitious with a pram, so we brought along our trusty Ergobaby carrier too for when he inevitably got sick of the stroller. The trail takes you past 16 historic landmarks – some of which are very cool and some less so – following this guide to learn about the significance of each stop. We walked as far as Copp’s Hill before getting the subway home for a pit stop back at our Airbnb.

In the afternoon, we took the subway to Harvard. The campus is stroller-friendly and lush, so it was enjoyable to simply wander around. It was a low-key outing that fit nicely into one of his longer wake windows. On the way back, we got off at North Station and walked along the Charles River Esplanade (which was really gorgeous in the sunshine) while R napped in his pram – even managing to walk all the way home.

This was the perfect first-day activity: outdoors (as I mentioned in my jet lag blog, daylight is crucial), flexible, and something you can shorten if the little ones get tired.

Things to do in Boston with kids: day 2 – a walk around Boston’s main sights

Another early start, and we took the subway all the way to the Bunker Hill monument (we didn’t go up it, given we had R’s pram with us) and explored the neighbourhood on our walk towards the USS Constitution. From there, we walked to Quincy Market for a pretty decent takeout-style lunch (with lots of options to suit all tastebuds!), before heading back to Boston Common and spending a bit more time looking at the various duck homages.

We then walked up Boylston Street, popping into the city’s huge public library (which had baby changing station) before a rest at our Airbnb. And then in the final wake window, we walked to the magnificent Fenway Park (and saw the aftermath buzz of an earlier game), which was pretty cool, despite not being baseball fans. You can do a stadium tour, which could have been fun, had we had more time.

Things to do in Boston with kids: day 3 – daytrip to Salem and Rockport

After two very busy days of walking, we fancied a change of scene (not to mention needing to find somewhere new to park the car, given that most of the streets seemed to have free parking only on weekends). So, we decided to see whether Salem was worth the hype (it wasn’t) and went on to explore a small coastal town that had been recommended to us, called Bearskin Neck, on Cape Ann.

We drove to Salem – famous for its witch trial history – while R took his first nap, which worked well for him but not so much for us, as it was pretty quiet there, despite it being around 9:30 a.m. We realised most of Salem’s shops and tours open after 10am, but even as we were leaving it felt empty – and there wasn’t really much to look at beyond a lot of tourist traps. I found it sobering to walk around the memorial park, but I was expecting a bit more in the way of visible history. They had a walking trail on the ground (much like Boston’s Freedom Trail), but it wasn’t very interesting. We parked at the train station, which was very easy.

From Salem, we continued on to Rockport and Bearskin Neck. This seaside town turned out to be a gem: colourful wooden houses, cute shops, and a peaceful harbour. We strolled along the waterfront and treated ourselves to an ice cream from Gifford’s (the s’mores one was delicious!).

We left Boston the next day and, regrettably, missed seeing the Boston Tea Party ship, which I’d suggest squeezing in if you can. We chose not to visit the aquarium after hearing locals say it wasn’t worth the money, knowing we would probably visit Montreal’s biodome, which offered R something similar. The only other thing I’d have liked to have done was a sunset harbour boat trip, but we didn’t want to jeopardise R’s bedtime. I also was recommended the duck tour boat, but didn’t feel it was that safe with such a young baby – but it would fun with older kids!

Where to stay in Boston with a baby or toddler

We stayed in a historic brownstone apartment in Boston’s South End, about a 30-minute walk or a short subway ride from Boston Common. The area felt safe, with coffee shops and restaurants nearby, and we stayed in a lovely old building with all the amenities we needed, including laundry facilities and a decent balcony/terrace. The downside was a little bit of car noise from the busy street outside (only an issue if someone was sleeping in the lounge), and we missed having a second bedroom for R to sleep in.

For families travelling with a baby, an aparthotel or Airbnb is often a great choice, especially if you want a lounge area to relax in after bedtime or space for little ones to roll around and play. That said, if you’re planning to be out exploring Boston most of the day, a family-friendly hotel can work just as well. Many Boston hotels now offer baby cots/cribs upon request, along with extras such as blackout curtains and mini-fridges. While not personal recommendations, some that have been suggested to me include the 4 star Marriott Long Wharf or the one at Navy Yard, and the 5 star Whitney Hotel.

Other popular areas to stay in Boston with kids include:

• Back Bay: Central, walkable, and close to the Public Garden. A great choice if you want to be in the heart of the action.
• Waterfront / Seaport district: Modern hotels with larger rooms and great harbour views. Close to the Aquarium and ferries, which makes outings with kids easier.
• Cambridge (near Harvard): A little quieter, with a leafy, studenty vibe. Still very well connected by subway and a nice option if you prefer a more relaxed base.

Browse a range of family-friendly hotels in Boston.

Where to eat in Boston with kids

When travelling with a baby, we find that food halls and takeaway spots are far easier than longer sit-down meals. In Boston, it worked brilliantly with R’s nap schedule and meant we could eat quickly (but well) without worrying about disturbing others. Boston has plenty of casual, family-friendly restaurants and markets that make eating out with kids stress-free.

Our recommendations for family-friendly places to eat in Boston include:

• Omni Parker House: Famous for inventing the Boston Cream Pie, this hotel bakery was on our must-try list. We picked up a takeaway slice while walking by on the Freedom Trail, and it was well worth the price – rich, indulgent, and perfect for sharing.

• Chilacates: A local favourite for Mexican food, with several locations across Boston. Their burritos and tacos are fresh and flavourful. It was easy to get delivery, so we had a tasty dinner back at the Airbnb while R slept.
• Crazy Good Kitchen: A brilliant burger spot with a couple of Boston sites, plus one in Salem if you’re out on a day trip. Great for a casual family lunch, but we had takeout.
• Boston Pocket & Deli: A neighbourhood gem near where we stayed. Their made-to-order bagels, subs, and sandwiches were great.
• Honeygrow: While not unique to Boston (you’ll find them all over the East Coast), this build-your-own noodle and salad bar is a good option for families, especially if you want something fresh and customisable.
• Quincy Market (Quincy Food Hall): One of the best food halls in Boston, and particularly good for families. There’s something for everyone, from clam chowder to pizza, but it’s especially good for lobster rolls. It’s not the cheapest given the plastic cutlery, but it’s convenient and fun.
• Boston Public Market: Smaller than Quincy but still great for a casual bite. Plenty of shops offering local food and other goodies.

Must-try Boston foods with kids

Boston has some iconic dishes that are worth sampling, even when travelling with little ones. Luckily, many of them are available in casual, family-friendly spots:

• Lobster rolls: You’ll find these everywhere, but Quincy Market is a good place to try one without committing to a full sit-down restaurant.
• Clam chowder: Creamy, warming, and easy to share a spoonful with kids if they’re adventurous eaters.
• Boston cream pie: Not a pie at all, but a sponge cake layered with custard and topped with chocolate. The one from Omni Parker House is the original and apparently the best.
• JP Licks: multiple ice cream shops around Boston and very tasty.
• Gifford’s in Rockport and other locations: Delicious homemade ice cream – my campfire s’mores flavour was one the best we had on our trip.

Supermarkets in Boston

Having a supermarket nearby makes travelling with a baby so much easier. We mainly used a nearby Whole Foods Market for breakfasts, but there are plenty of other options too. Trader Joe’s (like Lidl in the UK) is good for affordable snacks and frozen bits, and Stop & Shop works well if you need to do a bigger weekly shop or baby essentials like nappies (we used them throughout our stay in Cape Cod).

Family destinations near Boston: where to combine with your city trip

One of the best things about visiting Boston is how many family-friendly destinations are within easy reach, making it a solid starting point for a New England road trip with kids. On this trip, we combined our Boston city break with a road trip through Vermont up to Montreal, and then a week in Cape Cod. These were all very different but equally brilliant stops for families (destination guides coming soon!). Cape Cod is all about beaches, bike trails, and charming seaside towns, while Vermont offers mountains, lakes, and endless outdoor adventures. Montreal was a surprise – it felt arty and distinctly European in many ways, and we really enjoyed our three nights there.

Some of the other options we considered (and are contemplating doing next summer) include:

• Rhode Island, less than two hours away by car, is renowned for its sandy beaches and historic mansions in Newport.
• Bar Harbor in Maine, a little further away, is the gateway to Acadia National Park, which is perfect for families who love hiking and coastal scenery.
• New York City, just a four-hour drive away, could be a good option for combining a much bigger, bustling city experience with Boston’s walkable charm.

Boston as a family-friendly destination

Is Boston a good city to visit with kids? After a few days exploring with our 7-month-old, here’s our honest take on how it stacks up as a family-friendly destination, scored against our four key factors.

1. Getting there – ⭐️⭐️⭐️⭐️

Direct flights from London to Boston take just over 7 hours, although our outbound took only 6 hours and 20 minutes. Logan Airport is only 20 minutes from downtown Boston, and we didn’t need a car for our stay in the city, but it was cheap enough to get one for the whole fortnight road trip. Parking requires some consideration and can be expensive if you have to use a parking lot for the entire stay, but there’s plenty of free street parking between Friday PM and Monday AM. If you’re hiring a car for your road trip, we’d recommend searching with Discover Cars to compare the best rates.

The flight itself was actually much better than expected (I think we were nervous given it was our first long-haul), and this was largely thanks to the CoziGo creating a dark nap pod for R during his naps. I can’t recommend this enough, and it was equally brilliant on our pram when we were trying to protect R from the sun’s rays, or ensure a decent on-the-go nap.

2. Pramability – ⭐️⭐️⭐️⭐️

Boston is generally stroller-friendly, though there are some cobbles along the Freedom Trail, and some subway stations don’t have lifts. Luckily, our travel pram is lightweight (read our review here), and we could carry it down the stairs when needed. Plus, we made the most of our new LittleLife backpack carrier, which R loved sitting in (see our full carrier round-up for how it compares to others).

3. Adult fun factor – ⭐️⭐️⭐️

We enjoyed the mix of history, seafood, and easy walking routes, with plenty of museums to go to for adults and kids alike, should you have more time than we did. Had we not had a baby with us, we might have done a harbour boat trip and gone to a Fenway game, so there’s some compromise.

4. Cost – ⭐️⭐️⭐️

Boston isn’t cheap, especially for accommodation and tourist attractions. That said, many highlights are free, and it was easy to walk everywhere.

Overall, Boston made for a good city break with a baby. We loved how compact and walkable it was, spending plenty of time outside, and we could see how it would work well with older kids. Skip Salem if you aren’t too fussed on a guided tour, but don’t spend too long in the city – New England has so much to offer, and Boston, for us, really was just the start of an epic road trip.

Things to do in Boston with kids: FAQs

As always – keep up the adventure!
Allie, Jack & R x

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