36 Hours in Boston with Kids: The Perfect Family Stopover Itinerary
Every summer we head up to Cape Cod to visit my husband’s family and it’s become one of our favorite traditions. Cape Cod is such a beautiful place with amazing food, beaches and plenty to do with kids. But this year to save money on flights we needed to leave super early from Boston so we decided to add a day onto our vacation and explore Boston. Personally I love Boston! I’ve been a few times and always say if it wasn’t for the winters, I’d live there in a heartbeat. But this was our first time bringing the kids and I was amazed at how family friendly it is.
We spent 36 hours exploring and jam packed it with lots of fun. I can’t wait to spend more time there but if you are looking for a quick family getaway or have a long layover before flying out of Logan Airport, here's exactly how we spent a day and a half in Boston.
The swan boats in Boston Public Garden are an iconic site.
Where We Stayed
We stayed at the Hilton Boston Logan Airport because we had an early flight the next morning, and it couldn't have been more convenient. Being just minutes from Logan Airport meant we didn't have to stress about traffic or a long morning commute. It also gave us plenty of time to squeeze in one last swim before bed—a highlight for our kids after a full day of exploring.
Our kids always love a hotel swimming pool!
What We Did
Breakfast at Flour Bakery: Our first stop was breakfast at Flour Bakery + Café. It was the perfect location next to the Boston Children’s Museum and had both savory and sweet options for the kids and adults.
Boston Children's Museum: If you're traveling with younger kids, put the Boston Children's Museum at the top of your list.
We easily could have spent half a day here. Between the climbing structures, interactive exhibits, construction zone, and hands-on activities, our boys never wanted to leave. It's engaging for a wide range of ages and a great place to burn off some energy before heading back out into the city. Cost: Adults: $24, Children (1 – 15): $24, Infants (under 12 months): FREE
Walk Along the Harbor & See the Tea Party Ships: Just outside the museum, take a walk along the waterfront to see the historic Boston Tea Party Ships. Even if you don't take the full tour, it's a fun stop to admire the ships and soak in the harbor views. It's an easy addition to your day since it's only steps from the museum.
Boston Public Garden: This ended up being one of the most memorable parts of our trip. Our boys have been reading Make Way for Ducklings, so riding the famous Swan Boats was non-negotiable. They loved seeing all the ducks and naming them from the book.
Of course, we also had to stop by the beloved duckling statues, where plenty of families were taking photos and climbing alongside Mrs. Mallard and her ducklings. If your kids know the book, this stop feels a little magical. It’s also a great place to burn some energy! The park is huge and beautiful.
Stroll Newbury Street: After the park, we wandered down Newbury Street. It's one of Boston's prettiest streets, lined with brownstones, boutiques, cafés, and plenty of shopping. There are tons of sidewalk cafes. We grabbed a drink and a nibble at Faccia a Faccia since we were planning an early dinner.
Dinner in the North End: No visit to Boston feels complete without dinner in the North End.
We ate at LoConte's Italian Restaurant, and even though it wasn’t our first choice (make reservations if you can at places or plan to wait for a long time) it was incredible. The portions were large, the lobster ravioli was incredible and the atmosphere was exactly what you'd hope for in Boston's Little Italy.
After dinner, we joined the crowd heading to Mike's Pastry for cannolis.
One tip: Bring cash. The line moves quickly, but you'll want to be prepared so you don't miss out on one of Boston's most iconic desserts.
Delicious breakfast and coffee at Flour Bakery
The Boston Children’s Museum is so interactive and perfect for a family-friendly trip!
Nothing like stumbling on a street festival in Boston’s North End!
I’m still dreaming about this lobster ravioli.
Parking & Getting Around Boston with Kids
One thing we wish we had planned a little better? Parking.
We rented a car since we were flying out early the next morning, and while it gave us flexibility, parking around Boston was much more expensive than we expected. Between garages near attractions and parking in the city, it easily became one of the biggest expenses of our quick trip.
Boston's subway system (the "T") is usually one of the easiest and most affordable ways to get around the city, especially if you're staying downtown. During our visit, however, part of the subway was temporarily shut down for maintenance. With only 36 hours to explore and two young kids in tow, we decided it wasn't worth trying to navigate service changes and transfers.
If the subway had been running normally, I think we would have happily skipped the rental car altogether and relied on public transportation or rideshares. But given our tight schedule, having the car—even with the pricey parking—helped us maximize our time.
Our advice: If you're spending several days in Boston, consider skipping the rental car until you're ready to leave the city. If you do have a car, be sure to budget for parking because those costs can add up quickly.
If you're debating whether Boston is worth a quick family trip, the answer is an easy yes. We packed a lot into 36 hours, and somehow it still felt like we barely scratched the surface. What would you add to this itinerary?
