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A Family Guide To Exploring Boston

Hands down, our favorite thing to do as a family is travel. Living in New York City, there are plenty of places that we reach within a couple of hours by car, but since the world has reopened, it seems that traffic is worse than ever. So when it came time for another family trip to Boston, we left the truck parked in the garage, and hopped an Amtrak train to New England. And real quick,  if you’ve never been to Boston, you’re missing out. The city is packed with plenty of culture and activities, especially for families. The itinerary I share today is only a fraction of the wonderful things you can explore while you’re in this historic city. 
We set out for Boston from the new Moynihan Hall, located right in Penn Station, on the Northeast Regional, taking in the views and relaxing. As I sat abroad looking out the window, I was relieved that we weren’t stuck in the car, with the kids likely arguing with one another. This was our second Amtrak trip to Boston, so the kids were old pros making their way to the bar car for snacks and water. While they relaxed in their seats, I used the time to get some work done. Thank goodness for free wi-fi on board!


We left early in the morning, so we pulled into Boston before Noon. Our hotel for the stay was the Hotel Indigo, which is conveniently located across the street from the Boston Garden, in Boston’s Bulfinch Triangle Historic District. Once you’ve experienced it, you’ll learn that Boston is a walking city, so our hotel was about 15 minutes from the majority of activities on our agenda.

For me, the number one activity to do with your family when in Boston is Fenway Park for a baseball game! I know you may not expect to hear this coming from a New Yorker, but there’s something about the intimacy and old school charm of that ballpark. Unfortunately the Red Sox were down in Florida for spring training during our trip, but definitely make sure to add this to your list of activities. Even if the Sox aren’t in town when you are, the stadium offers tours of the facility, which are tons of fun for the kids.

Our first afternoon in town, we headed for lunch at an oldie but goodie, Regina Pizzeria (originally called Pizzeria Regina). Founded in 1926 by Luigi D’Auria in Boston’s North End neighborhood, Regina is now a regional pizza chain throughout New England. This pizza spot is always our go-today when in town.

After some pie, we made our way to Cambridge to visit the Harvard Museum of Natural History. We used our CityPASS for access, which allow discounts on attractions throughout the city, including free admission to four attractions. The museum is located on campus of Harvard University, and definitely a highlight of my kids trip. I loved that while there was a lot to see, the exhibits are not overwhelming. We especially enjoyed exploring the animal exhibitions as this is what my daughter is studying at school at the moment. Following the museum, we took advantage of the glorious spring weather, and strolled around Cambridge Common and John Fitzgerald Park. Such a cool playground area for kids, and an adorable little park for a picnic!

After a full day of travel and exploring, we stopped back at the hotel to change for dinner. That evening. we dined at Limoncello, a delicious Italian restaurant, less than a 10 minute walk from our hotel. The North End has no shortage of Italian restaurants and this one did not disappoint. The kids said it was one of their favorite pasta dishes they’ve ever had!

From there, we needed to fill the sweet tooth, so it was over to Bova’s Bakery, a few blocks away. From cream and jam-filled treats to cakes and chocolate, they literally had everything you could imagine in a bakery. The cannolis were absolutely spectacular, and we loved how the staff was filling the shells with fresh creme right in front of us. Sure, we may have waited on line stretched around the store and out the door, but the pay off is worth it! And Bova’s can satisfy a craving any time of day, because they are open 24 hours!

The next morning, we walked over to Tatte Bakery & Cafe for some breakfast. The bakery had a great little dining area outside and a wonderful welcoming feel inside space. They had some great coffee and absolutely delicious breakfast treats to choose from. From omelettes to croissant sandwiches, I think my family ordered most of the menu. Another great food joint, less than a 10 minute stroll from our hotel.

From there, we walked over to the harbor for a city cruise with Historic Harbor Cruise. If you really want to see some breathtaking views of the city, Historic Harbor Cruise is the way to go. In addition to the sites, the staff guides on board offer up some very interesting information about some of its iconic landmarks like the USS Constitution, Old North Church, Boston Light, the Boston Tea Party ships, and the Boston Museum. The weather didn’t cooperate for our voyage, but some of the clouds managed to break before we made it back to shore.

After the cruise, it was over to the New England Aquarium, with admission covered by my Boston CityPASS. Their coral reef exhibit features over 1,000 marine animals, a tidepool touch tank, a penguin habitat, a pet sea star, and so much more. With four levels, you can spend an entire afternoon walking around watching and reading about its incredible tenants.

After that, it was on to Sam LaGrassa’s for lunch. Yum! They serve up a huge variety of sandwiches like their world famous Rumanian Pastrami, classic sides like coleslaw, and and some of the fattest tastiest fries I’ve ever had. Don’t worry, if you’re vegetarian, they have you covered with meatless options – maybe a buffalo mozzarella sandwich or a veggie wrap.

After lunch, it was raining so we rode over to the Museum of Science to see what it had to offer. Again, our CityPASS came in handy for entry, and not reservations were required. The thing I really loved about this museum is that I could do more than just look at exhibits. These 700 exhibits were actually interactive, which makes it so much more interesting. They also have the Charles Hayden Planetarium and the Mugar Omni Theater, so if you have time for one their many scheduled shows, you can make an entire day out of a single museum visit. With the only domed IMAX screen in all of New England, it is quite a special place!

Back at the hotel, we changed our wet clothes and rested our feet, before walking over to Ma Maison for dinner. This restaurant features high-class French cuisine with a relaxed atmosphere that we really enjoyed. They have all kinds of delicious options from seafood to steak, so there’s something for everyone. It was a cozy spot that will now always be on our list for when in Boston. I mean you cant go wrong with mussels and steak frites!

The next day was our last in Boston, so we had to make it count. The morning started with a walk to South Street Diner to enjoy some rib sticking breakfast to power us through the day. South Street Diner, formerly the Blue Diner, was built in 1947, and over the years, the Diner has become a local landmark, and a staple in Boston’s after-hours scene. We had a breakFEAST, including some amazing pancakes, omelets, and home fries. Good ole fashion diner food at its best!

The weather broke, so we couldn’t leave town without taking in the epic park of Boston Commons and the boutiques of Newberry Street. Boston Commons which is bustling with life, even in the morning hours. Last time we were in Boston, the kids took the cutest photo on the Make Way for Ducklings statues in the Commons, so I was excited to recreate the pose years later. And on Newberry Street, I couldn’t resist dipping into some of my favorite shops.

And finally, it was time to jam in one last bit of sight seeing before we left, on Boston’s North End Pizza & History Walking Tour. It’s exactly what it sounds like. You embark on a walking tour of Boston while stopping to eat pizza at three of the town’s favorite pizza spots! It doesn’t get much better than that. The tour took us along the Freedom Trial where our guide preached about historic sites like Old North Church and Paul Revere’s House. As if the pizza wasn’t enough, and at the end of the tour guests were treated to some cannolis from Modern Pastry Shop. Come on!!!

After finally, it was time to head back home. We grabbed our bags and headed back to South Station, for our afternoon Amtrak Northeastern Regional train. Since we had a fun filled day and action packed weekend, the soothing motion and sounds of train allowed us all to take a much needed nap. After all that, I couldn’t have imagined 4-6 hours stuck behind the wheel in traffic. Visiting Boston was an absolute blast! Amtrak made it a breeze to get to and fro, and CityPASS granted us access to plenty of cool places to explore!

This post was originally published April 26th, 2022*

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16 thoughts on “A Family Guide To Exploring Boston”

  1. I need to make a return trip to Boston. The last time I was there was in 1999! My favorite thing about the city is its history. Even if you only a casual history buff, there is so much to see and learn about.

  2. Being from Massachusetts, this is something I do very often! I love the New England aquarium. It’s one of my favorite places to visit. Awesome pictures, thanks for sharing!

  3. Jennifer Prince

    Ah!! It looks like you had such an amazing time. I haven’t been to Boston (or New England) in forever. I need to head back!

  4. Haven’t been to Boston and hopefully I can be able to visit it too. I really love to see family traveling together. This is my dream when I already have my own family.

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