Where to eat, what to see and how to make the most of vacationing with kids in Boston. All the details about our family trip to this beautiful, historic city.
We just got back from the most incredible trip to Boston with our four kids (ages 9-14), and I couldn’t wait to share everything we did!
Boston has always had a special place in our hearts! We lived in Cambridge years ago while my husband, Brandon, went to business school and while I worked at the school he attended. Our oldest, Baker, was actually born in Boston just before we moved away, so this trip was the perfect blend of nostalgia and family adventure.
I planned the trip by breaking the city into sections each day so we could explore efficiently without feeling rushed, and it worked beautifully. Boston is so walkable, full of history and great food, and packed with fun things to do for every age. Here’s how we spent 5 perfect days (really 4 full days and 2 half days) in one of our favorite cities:
Day 1: Evening Arrival & Late Dinner
- Arrived late evening
- Checked in to the Four Seasons Place which is right across from the Boston Public Garden and Boston Common. Highly recommend this hotel for location, comfort, and family-friendly service!
- Late-night dinner at Contessa on Newbury Street. This restaurant had the most stunning views of the city lit up at night and a deliciously creative Italian menu. It was probably our favorite meal of the trip (loved every dish!) – and we had several incredible meals. Perfect way to kick off the trip!
Day 2: History & The North End
- Breakfast at Thinking Cup
- Walked through Boston Common
- Started The Freedom Trail using a $3 map from the Visitor Center – great way to go at our own pace! We had the kids take turns reading the history and significance of each stop on the trail.
- Quick stop at the Omni Parker House hotel for the iconic Original Boston Cream Pie and Parker House Rolls in the Parker’s Bar
- Lunch at Union Oyster House – the oldest continuously operating restaurant in America. Had to get the clam chowder and Boston Cream Pie!
- Apple Cider Slushies and mini cider donuts at Red Apple Farm inside Boston Public Market
- Shopping and exploring Quincy Market and Faneuil Hall
- Walked through Beacon Hill to shop and stop at the charming Beacon Hill Books & Cafe
- Walked through Boston Public Garden to see the Make Way for Ducklings statues and watch the Swan Boats
- Rest time at the hotel before getting ready for dinner and exploring the North End
- Evening in the North End – playtime at Langone Park, dinner at Antico Forno (great pizza, pastas, and takes reservations!), and our traditional stop at Mike’s Pastry (still our favorite cannoli!)
Day 3: Cambridge + Lobster & Memories
- Grabbed pastries at Flour Bakery in Boston Common and took the T to Harvard Square
- Explored Harvard and Harvard Square, stopped at The COOP and Harvard Book Store (they had my cookbook, Brilliant Bites, in stock!)
- Burger lunch at the quirky and classic Mr. Bartley’s Burger Cottage
- Ice cream at JP Lick’s – still just as good as we remembered!
- Crossed the Charles River to see Harvard’s historic football stadium and Harvard’s Basketball Pavilion – the boys loved this!
- Walked around Harvard Business School – had so much fun showing the kids around our old stomping grounds and recreating baby photos with our son Baker in front of Baker Library (which he was named after!), and even visited Brandon’s old classroom.
- Walked by our old home on Hingham Street in Cambridge, complete with its 1854 charm and the speakeasy-turned-laundry-room in the basement.
- Afternoon snack at Alive & Kicking Lobsters – their lobster sandwich is a delicious gem! So simple yet so sweet and succulent.
- Met a dear friend from HBS for cocktails at Brick & Mortar (amazing drinks and bar vibe!)
- Dinner at Basta Pasta – order the homemade fusilli Bolognese and pizza! This used to be our go-to neighborhood restaurant and it was just as delicious as we remembered.
- Ice cream stop at Christina’s (nostalgic, but JP Lick’s wins this round)
Day 4: Fenway & Views
- Slept in and headed to Fenway Park for the Red Sox vs. Astros game. Fenway hot dogs, ice cream in souvenir helmets, and a chance for the kids to run the bases = perfect quintessential family baseball experience!
- Walked across Harvard Bridge to look around MIT and then strolled along the Charles River (closed to cars on Sundays!)
- Explored Newbury Street, the Boston Public Library, and went up to View Boston at the Prudential Center – stunning panoramic views of the city!
- Fun Duck Boat Tour from the Prudential Center – the kids loved driving the boat when we went into the Charles River!
- Dinner at Saltie Girl – the chowder and lobster roll were our favorites of the trip!
- Ice cream (again!) at JP Lick’s on Newbury Street – top flavors: peanut butter cookies & creme, mint cookies & creme, coffee cookies & creme, and brownie brownie batter. Yum!
Day 5: History, Sports & Waterfront Fun
- Morning pastries at Tatte Bakery – lots of locations around Boston and an amazing assortment of pastries and breakfast foods to choose from!
- Morning at the USS Constitution Ship and Museum
- Noon tour of TD Garden plus a stop at CardVault sports card shop since the boys are obsessed with sports cards right now.
- Lunch options: Dim Sum at Dynasty in Chinatown OR James Hook & Co on the waterfront for fresh seafood
- Afternoon at the Boston Tea Party Ships & Museum – fun, educational, and the kids loved throwing tea overboard!
- Walked the waterfront and checked out the New England Aquarium
- Dinner at Giacomo’s – North End classic that we used to love! The service was great, but sadly, the food just wasn’t as good as it used to be. (cash only & no reservations)
- Dessert showdown: enjoyed Modern Pastry and Bova’s, but Mike’s Pastry cannoli still wins our hearts!
Day 6: Last Hurrah
- Final stroll (and shopping) along Newbury Street
- Brunch at Stephanie’s on Newbury – we got a beautiful table on the patio where we could people-watch while we ate. The food was way better than we remembered – loved the mezza platter, lobster roll and turkey club sandwich.
- More JP Lick’s (of course!)
- One last walk through Boston Public Garden
- Off to the airport
Tips for Visiting Boston with Kids
- Break the city into regions each day to maximize efficiency.
- I added Google Maps links for each location to our itinerary so we could easily just click the link to get directions and learn more. I’ve added the links to our itinerary above so hopefully this helps y’all too!
- I also added our detailed itinerary with all the Google Maps links to a shared Notes on my phone and shared it with Brandon so we could both easily navigate, if needed. I also shared it with the boys and they LOVED being able to see the plan, where we were going next, and even navigate us from place to place. By the second day, they were leading the way and pretty much telling us what we were doing next. I really do think this was a “trip changer” as far as how amazingly smooth it all went since kids usually thrive when they have a schedule and know the plan.
- We also didn’t have strict times on everything we did so it was nice to not have to rush from place to place. We kept a pulse on the kids and whenever we felt they needed a break from walking or absorbing history, we would let them stop at a park or basketball court to play around or we’d find a treat to sit and share.
- Walk when you can (we averaged over 20,000 steps per day!), but it didn’t feel like it because there is something to do and see each step of the way.
- Take the T for fun and convenience. It’s so easy and clean to use.
- Don’t skip the cannoli, lobster rolls, clam chowder, Boston cream pie, all the Italian foods, or ice cream at JP Lick’s, of course! 😉
Questions?
If you have any questions I didn’t cover above, leave a comment below and I’d be happy to fill you in more from our experience. You can also check out my Boston Instagram Story Highlight for all the behind the scenes fun during our trip!
This trip exceeded all our expectations – it was a perfect mix of nostalgia, food, fun, and history. Boston is such a walkable, clean, and family-friendly city, and we loved seeing it through our kids’ eyes. The memories we made, especially sharing our old stomping grounds in Cambridge and HBS, were truly priceless.
xoxo,
