family travel

Exploring Boston with Kids: Family-Friendly Fun

/ Melissa (I Crashed the Web) / Leave a comment

I love Boston! It’s a city full of history, with plenty to do, and easy to get around. Plus, Boston holds a special place in my heart — it’s where B and I met while at Boston College! I love the city, and we recently went back with our kids for the first time. I hadn’t been back since I was pregnant with FW in 2016 and found that the city is still incredibly walkable, packed with history, and surprisingly kid-friendly.

Spending time in Boston looked a little different from it did when I was in my 20s – but there were still so many fun things to do! Whether you’re visiting for the first time or returning with little ones in tow, here are some of our favorite ways to enjoy Boston as a family.

Getting Around

Boston’s public transportation system (the “T”) is easy to navigate and a fun adventure for kids. Ours loved riding the train—and bonus: kids ride free! We just purchased a week-long adult pass and we were good to go for our 7-day stay.

Where to Eat with Kids

The North End (Little Italy)

Whether you’re with kids or not, this charming neighborhood is a must-visit. It’s packed with Italian restaurants, and most are kid-friendly, especially if you dine out for dinner early. A few favorites:

  • Mike’s Pastry – Iconic cannoli tourist spot. It’s cash only, but worth it! We tried other cannoli places in the North End but this still came out on top.
  • Pizzeria Regina – Famous Boston pizza with a location in the North End.
  • Lucia’s – A cozy spot we’ve enjoyed in the past (reservations available).
  • Nando’s – Great for families! They even made off-menu spaghetti and meatballs for our kids. They also take reservations.

Prudential Center

  • The food court – Options for even your pickiest eaters.
  • Legal Sea Foods – I’m not saying this is THE PLACE to go for the best seafood in Boston. Yes, it’s a chain, but it’s a Boston staple with a kids’ menu. They have several spots, but went to the one in the Prudential Center, which is easy to reach by T.

Quincy Market at Faneuil Hall

This is bustling food hall where everyone can find something they love, or at least everyone in our family did. From orange chicken to acai bowls to hot dogs to clam chowder, there really is a great selection here. Warning – if you go on weekends it’s BUSY and hard to find a seat, but weekdays are less packed and more manageable, especially with hangry kids. There are often free samples in the market and street performers outside too!

Ice Cream

We went in the summer, so yes, ice cream deserves a category of its own. Here are a few local spots:

  • JP Licks – A local ice cream favorite with spots throughout the city.
  • Gelato in the North End – Always a hit after dinner, if you end up not stopping at Mike’s (or even if you do!).
  • Jamie’s Ice Cream – Smaller place with outdoor seating in Brookline but right off the T. Their flavors are so good, I love “Dump Him” the most!
  • White Mountain Creamery – A staple if you’re near BC

Fun Things to Do with Kids

Boston Duck Tour

A land-and-water tour with a pirate guide and lots of quacking. Super touristy, but the kids loved it. Look for early morning discounts or combo tickets with other attractions. We took the 9:30 a.m. tour to snag the early-duck discount. This was one of the highlights of the trip for sure! The kids loved “driving” the boat when it went off the land and into the water.

Boston Public Garden

Ride the swan boats and visit the Make Way for Ducklings statues. A peaceful, picturesque spot for a stroll.

Freedom Trail

Follow the red line through historic sites like Paul Revere’s house. Great for older kids or history buffs. We only did some of this with our kids, since the 3-year-old couldn’t care less – but I’m hopeful my older kids will remember some of what we saw when they learn more about the American Revolution!

Boston Common

America’s oldest public park, and it’s perfect for running around or relaxing.

Newbury Street

Upscale shopping and dining but there are fun kid-friendly stops like a Harry Potter store and Ben & Jerry’s. Beautiful for just walking down on your way to the Boston Public Garden.

Faneuil Hall & Quincy Market

Shops, food, and entertainment all in one place. We got souvenirs, lunch, and walked around a few times. Our kids loved the street performers (and yes, there was some breakdancing involved by my oldest, too!).

Sports!

Our kids enjoy watching professional sports teams, and Boston has plenty to choose from. Since we went in the summer, we caught a baseball game at Fenway and it was great for the kids to see some ball in America’s oldest ballpark. (See a pattern? Lots of OLD things in Boston!)

Playground & Splash Pad

There are playgrounds throughout the city, but one that we frequented a few times was right outside the Government Center T stop and made for a quick break on our way to and from the T.

Rainy/Hot Day Options

  • New England Aquarium – A highlight of our trip! Penguins, sea turtles, and touch tanks. Our 3-year-old still talks about touching a sting ray and watching the penguins eat.
  • Museum of Science – A bit harder to get to, but worth it if you have time.
  • Boston Public Library – Beautiful and right near the Boston Marathon finish line, which is worth checking out, as well as the memorial.
  • The Prudential Center – A big, air-conditioned mall with food and shops (mentioned above also).

Bonus: Visit Boston College

If you’re near Chestnut Hill, consider a visit to Boston College! It’s where our story began! Stop by Cleveland Circle for a bite to eat at Pino’s Pizza and let me know if you want other food or coffee recs nearby.

Final Tips

Boston is a city best explored on foot or by T. We’ve driven and parked in our hotel before, but this time we flew into the city and took the T from the airport to our hotel. We also discovered a VERY affordable bus to and from downtown to the airport (Logan Express is FREE to downtown and just $3 to the airport). From Fenway to the North End, everything is accessible and easy to get to! And if you do make it to Mike’s Pastry, grab an extra cannoli for us, it’s now FW’s new favorite dessert!

Here’s some more inspiration from my recent Instagram reel:

A Few Days in Ithaca

/ Melissa (I Crashed the Web) / 1 Comment

And just like that, the vacation that I have been looking forward to for several months is over. Earlier in the year, we had planned a short getaway with my parents and brother. We had decided to check out the Finger Lakes, finding an AirBNB in Ithaca that would host us for the few days. My brother flew in from Berlin, my parents drove in from Albany and we all stayed together.


The trip was great. It was so wonderful to be able to spend time with my family, and LM and FW loved all the “Nonna, Grandpa, Sweetie and Uncle Greg” time. We also had a good time checking out the city and some nearby sites. Some of the highlights included:

Grabbing dinner and ice cream around Ithaca Commons.

Hiking to and splashing around Taughannock Falls.

Lunching and wine tasting at Thirsty Owl Winery.

Exploring the area – I went running along their waterfront path one day and my family and I took walks as well.

It’s always hard to finish vacation, but this one is especially hard because of the great family time we had.  I don’t know when my parents, brother and I will be all together again!

Some questions for you:

  • Have you been to Ithaca?
  • Do you vacation with your family?

Visiting Annapolis with a Toddler

/ Melissa (I Crashed the Web) / Leave a comment

A few weeks ago, B, FW and I took our third vacation as a family of three. (The first was a weekend in Columbus when FW was 2 months old, the second was a trip to Atlanta/Cincy/Asheville when FW was 8 months old) After our time in New York seeing my family and friends, we hit the road for another car trip – this time, to Annapolis.

I had never been to the city before, and in our few days there, I really liked it. I would definitely visit again and recommend it if you are traveling with a baby/toddler. (Side note: Is FW really a toddler? It’s hard for me to believe, but at 14 months, he sure is close to being one if he isn’t already.)

Here are some ways to pass the time if you go:

Walk down Main Street and check out the water. View the boats, get a bite to eat, and take photos of the water. We did this each day we were there. With FW we watched the ducks in the water, “woofed” at the many dogs that were walking by, pointed at the many boats and read the historical markers along the way.

Tour the Naval Academy. Most of this tour was pretty toddler friendly – it was a lot of outdoors, walking (or strolling) around, and FW was able to walk or sit and be somewhat loud (he’s at the age where he likes babbling AND shrieking) while we got the scoop. The only parts that were difficult? The chapel and John Paul Jones tomb – both were not places that were built for running/shrieking babies. 

A highlight of the tour? The noon formation. All of the students (or midshipmen as they are called) line up and do roll call at noon before lunch and the band plays some music as well. FW and I enjoyed this part very much!

Take a walking tour. While this tour was a great way to get an understanding of the history of the area, it wasn’t FW’s favorite. In full disclosure, I wouldn’t necessarily call this a toddler-friendly activity, especially if you have a toddler who likes to walk, talk, run and touch every single thing. The constraints of the walking tour (walking when the guide was walking, not touching the historical exhibits, etc.) were a little too much for FW. The tour was also 2+ hours, something that most toddlers may have a hard time following.

Going out to eat. And by out I mean OUTSIDE. We lucked out with the weather while we were in town and got to enjoy a few meals outdoors. I find patios much more FW-friendly (we can get up, walk, be loud, etc.) and Annapolis had quite a few of those. My favorite restaurant while we were there was The Iron Rooster- we actually ended up going there twice – once for brunch and once for lunch – and they even had a kids menu and crayons for FW to color with.

Get ice cream. I made it a goal to get ice cream nightly, and FW enjoyed sharing cones and cups with us. He enjoyed my peanut butter ice cream and B’s chocolate.

Find a playground. Let’s face it – most of the activities we did weren’t made for FW. They were baby-friendly activities, but they weren’t necessarily things he would enjoy doing. So, we made sure that we did find some ways for him to have fun and one of the things we did was find a playground. The playground at the Annapolis Elementary School was perfect! It had kiddie swings, little slides and plenty of area for him to play and run around. We went there before dinner one night and he got so tired out he slept for the first part of our meal, which as any parent knows, is great!

Some questions for you:

  • Have you been on a vacation with a toddler recently? What activities do you recommend?
  • Have you been to Annapolis?