We started a new family tradition this year, and I already know it’s going to be one of my favorites. When each of our kids turns 12, we’ll take them on a one-on-one mom and dad trip. Just the three of us. We borrowed the idea from friends here in Utah who do milestone trips with their grandkids, and we adapted it into our own thing, like we do with most things in life. Our son just turned 12, and we decided on Boston, mostly because there was a World Cup game happening while we were there and he is obsessed with soccer. The timing and the players lined up perfectly. We watched Norway play France and it was phenomenal. The energy in Boston right now is unreal!
That game ended up being one of our favorite things we did, but obviously that’s not on the calendar for everyone planning what to do in Boston, so I wanted to share the rest: the food and the activities that felt kid-friendly and hit a good mix of history and fun. I would highly, HIGHLY encourage you to find any way you can to take your kids one-on-one, just you and your spouse, because we had so much fun and I know none of us will ever forget it.
One tip that genuinely saved us so much planning time: before the trip, I gave ChatGPT our itinerary, told it who was traveling and what we already had scheduled (like the World Cup game and the Red Sox game). I asked it to help map out where to eat and what else to do around those spots each day. It brought up all the places we already wanted to go and told us exactly when to visit them. Total game-changer for making the most of a short trip!
Good eating is the most important part of any vacation in my opinion, so let’s start here.
NORTH STREET GRILLE
North Street Grill was recommended to us a couple different times for brunch, and it blew our socks off! We got there around noon on a late morning, later than the early crowd, and the wait wasn’t bad, but I’ve heard mornings can get busy, so get there early or make a reservation. I got the sweet and salty sandwich and I still think about it every single day.
CARMELINA’S
Carmelina’s in the North End, Boston’s Little Italy, is fantastic. I got the lobster ravioli and my husband Chad got a lobster dish that was just as good. The one thing we never managed to snag in Boston was a lobster roll. We regret it; every place we tried was completely packed. A lot of these spots are small, so know you might wait a little, or call ahead for a reservation.
PINOCCHIO’S PIZZA
Pinocchio’s Pizza in Harvard Square is a tiny little pizza joint that tons of famous people have visited over the years. The service was great, it’s old school in the best way, and the pizza is top notch.
MIKE’S PASTRY
The line at Mike’s Pastry at 9 pm was longer than you can imagine, but the cannolis are worth it. I didn’t even know I liked cannolis before this trip, and we went back twice because they’re that good. There’s a busy location in the North End and a quieter one near Tom Brady’s store.
REGINA PIZZERIA
Regina Pizzeria is known for seafood and pizza like a lot of Boston is. We grabbed it to go and ate in Faneuil Hall Marketplace, and it was the perfect quick bite in between exploring.
FENWAY PARK TOUR
Besides the World Cup game, my favorite thing we did was the Fenway Park tour. It was so fun! Our tour guide was an older guy who clearly loved the Red Sox, funny and endearing the whole way through. We went to a game right after. If you’re buying tickets, skip the Groupon-style resellers – it’s cheapest straight from the MLB website – and buy early because things sell out fast. If you’re in Boston while the Red Sox are playing, go. The energy is unbeatable.
USS CONSTITUTION
I personally loved the USS Constitution, a giant ship that never sank. We toured it on our own since there are plenty of signs to read along the way, so it’s easy to self guide.
DUCK TOUR
The Duck Tour was another favorite – you ride out on the water in an actual duck boat, they let you drive it for a minute and snap a picture, and you learn a good chunk of history without sitting through a five-hour tour, which none of us wanted anyway.
FREEDOM TRAIL
We also did the Freedom Trail, though not the guided version. We picked the stops that interested us most and worked them into the trip as we went, rather than doing the whole thing start to finish. We actually talked to a couple who did the full guided tour and they said they left early because they got bored. Picking and choosing worked great for us.
HARVARD SQUARE
Harvard Square and Harvard itself are right next to each other and are both worth wandering. My husband was fascinated by it, our son liked it too, and the gift shop is really cute. We even learned some fun facts about Legally Blonde while we were there. This is also where we grabbed that Pinocchio’s pizza, and there are so many cute little shops tucked around the square.
QUINCY MARKET
Quincy Market is the spot for souvenirs, food, and shopping, and it’s where we picked up most of our Boston keepsakes. Heads up that a lot of vendors are cash-only. We walked through twice during our trip, mostly to eat, but also just to soak it in. There are street performers everywhere and cobblestone streets that make the whole area feel so charming.
BOSTON MASSACHUSETTS TEMPLE
If you have the chance, go visit the Boston Temple, whether or not you’re a member of the Church of Jesus Christ of Latter-day Saints. It’s tucked in a quieter part of the city you wouldn’t stumble into just wandering around, and it’s beautiful. We went and did baptisms for the dead with our son, and the font there is unlike any other I’ve seen – you actually get to sit around it closely. There was such a wide range of people there that day, and it was a genuinely amazing experience! Even if you just want to walk the grounds, it’s worth the trip.
WHERE TO STAY (AND HOW TO GET AROUND)
We stayed just outside the city, and honestly, I wouldn’t do that again. Both Chad and I agreed that next time we would stay closer to the harbor, in the North End, since that’s where we ended up spending most of our time anyway. There are a few Marriotts right around the harbor that looked lovely and put you within walking distance of everything.
My other tip is to ride the subway. We rode it a lot on purpose because we wanted our son to experience it, and we even let him navigate us around a couple of times. It was such an easy way to get around, and it became part of the fun of the trip, not just a way to get from point A to point B.
+++
Boston ended up being equal parts busy and laid back, and every single person we met was kind. The charm of the old houses and the tiny restaurants that have been serving the same recipes for decades is real, and the Boston spirit is real too. I loved it, I want to go back as soon as possible, and I would put it at the top of your next trip list!
If you liked this post…
View Comments +