Boston Vacation with Kids: Historical, Fun + Delicious!

Boston makes a great kid-friendly vacation destination, especially if your family includes some history buffs. Plus, it’s an easy drive from either the Catskills or NYC. Since we live in Brooklyn and are used to walking everywhere, our top priority was to stay right on the Freedom Trail and explore the city by foot. And since I’m a food writer, I wanted to plan for some delicious meals along the way.

We visited Boston last summer with our 10-year-old son and 7-year-old daughter (back when we were still wearing masks outside) and wanted to share our hotel recommendation, the historical highlights, fun finds for younger kids, and the tastiest things we ate.

Will kids have fun on Boston’s Freedom Trail? That really depends on the kid. Our 10-year-old is deeply interested in the Revolutionary War and has lots of walking energy. Our 7-year-old? Note the sulking in the photo above.

WHERE TO STAY WITH KIDS IN BOSTON:

We stayed at the Bostonian, which we found to be the perfect location. It’s right next to Faneuil Hall (with lots of street-performers and shopping—Ramona bought many Jibbitz at the Crocs shop and went wild in the IT’SUGAR candy store). It’s right on the Freedom Trail (Archer’s ultimate walking path, with 16 historical sites along its 2.5-mile span). It’s steps from the Boston Public Market (where you can get a really solid breakfast every day). It’s also a quick walk through the Rose Kennedy Greenway (a fountain-filled, very kid-friendly park) to Boston’s North End, a fun and busy Italian neighborhood, filled with great restaurants and renowned pastry shops.

At the Boston Tea Party Museum, guests are invited to fling a weighted “box of tea” over the side of the ship.

WHAT TO DO WITH KIDS IN BOSTON:

If you only do one historical thing with your kiddos in Boston, make it a trip to the Boston Tea Party Museum. Get your tickets in advance—you really don’t want to miss this. Our guides were in full-costume and fully in-character. The exhibits are truly magical. (I won’t give anything away but museums were definitely not this cool when I was a kid!) And then, to top it all off you get to board a full-scale replica of the Boston Tea Party ship and fling a faux box of tea off the side. After immersing ourselves in the realities of Boston circa 1773, I have to admit that this felt pretty exhilarating.

Aboard Boston’s U.S.S. Constitution, every cannon has a name, like Brother Jonathan, True Blue, Mad Anthony, and Raging Eagle.

If you can handle a little more history, get on board the U.S.S. Constitution, a.k.a. Old Ironsides. At 220 years of age, she (yes, we’re calling the ship “she”!) is one of the 6 original ships of the United States Navy and the “oldest commissioned warship afloat in the world.” Her crew of active-duty U.S. Navy sailors seemed delighted by our kids’ questions, and there were good vibes all around, even for those of us (me!) who get very upset by war movies and don’t usually like to spend vacation days surrounded by cannons. Wear comfortable shoes here and be prepared to climb up and down some steep stairs/ladders to see the whole ship.

Boston’s Greenway Carousel, featuring a menagerie of hand-carved animals and mythical creatures, was our 7-year-olds favorite part of the trip.

Got a kid who just wants to eat candy, shop, and play? Our 7-year-old, Ramona, was able to handle a whole lot of historical sites because she knew she’d get a ride on the gorgeous Greenway Carousel when we were done. We made multiply visits, hopping on as many hand-carved animals and mythical creatures as we could. The whole Rose Kennedy Greenway is a fun place to explore, and it’s a great place to splash around in fountains with local kids on a hot summer day.

The Popover Lady’s cinnamon sugar popover is deliciousness itself. Pairs perfectly with a cup of coffee and a stroll long the Freedom Trail.

WHAT TO EAT WITH KIDS IN BOSTON:

If I could only eat one bite of food in Boston, I’d go back for this giant cinnamon-popover from The Popover Lady kiosk in Boston Public Market. It was seriously the best $3.50 I’ve spent in years. The market opens at 8am Monday through Saturday (but not until 10am on Sundays), so you can pop in for an early cup of coffee and a bite to take on the road. Also, your Boston vacation isn’t complete until you’ve tried a Boston cream donut from Union Square Donuts. Both the popovers and donuts are big enough to share.

We just scratched the surface on all the deliciousness Boston has to offer, but our favorite family meal was at The Daily Catch, which has several locations around town. We couldn’t snag a reservation at their Waterfront spot, so we ended up at the original North End location, where I got a tangle of homemade black pasta with fresh scallops, earthy mushrooms, sweet peppers and onions, doused with olive oil and anchovy butter. The kids got linguine with white sauce and ate so much they nearly burst.

I also loved Neptune Oyster, a tiny, high-end, walk-in-only seafood spot in the North End. There’s no kids’ menu here, and I don’t really recommend it for most children, but mine fell in love with the Fried Ipswich Clams, which were the most airy, crispy, sweet and juicy fried clams I’ve ever had.

All in all, it was the perfect way to spent a couple of delicious summer days learning about American history and making memories together.