Boston: A Family-Friendly Travel Guide For All Seasons

Vanessa and her girls on the Freedom Trail, and a sign for Boston Commons
Walking Boston’s Freedom Trail.

A couple of months ago, my family and I took a trip to Boston and surrounding towns of New England. With two young girls in tow, we had to make sure we were choosing family-friendly activities that we could all enjoy — and what a great time we had!

America’s Walking City

If you’re a history lover, strap in because there’s lots of it in Boston. It is one of the oldest cities in the country and where the American Revolution began. This was our second time in Boston, and we love how walkable the city is, but we also liked having the option of hopping on and off the Old Town Trolley. It’s a wonderful way to get around the city while sightseeing along the way. Then, you can hop off and explore by foot whenever something catches your eye.

Speaking of walking, take a stroll down the famed Freedom Trail, a 2.5-mile red-brick trail that takes you through Boston’s historic sites. It begins at Boston Common and ends at Bunker Hill Monument. Along the way, you can visit King’s Chapel, Faneuil Hall, Paul Revere’s house, and other interesting sites. 

All aboard the U.S.S. Constitution! Along the Freedom Trail, you’ll also find one of the six original ships of the U.S. Navy, built over 220 years ago. You can hop aboard and explore this magnificent historical site next door to the U.S.S. Constitution Museum. Here, you can also view the U.S.S. Cassin Young in the museum’s Navy Yard. The museum itself is filled with interactive exhibits and hands-on programs that are fun for all ages.

Boston has a few notable parks. One of the most renowned is Boston Common, the oldest public park in the country. This gem nestled within the city of Boston was founded in 1634. We loved exploring this beautiful park, and I remember visiting during the fall when it was even more impressive because of the vibrantly colored leaves amongst all the trees.

The Boston Public Garden was the first public botanical garden in America. You can walk the meandering paths of this Victorian-era park and discover the lagoon, monuments, fountains, and plenty of flora. Visit during the springtime to admire the brightly colored blooms.

For another trip back in time, be sure to visit the Boston Tea Party Ships & Museum. Learn all about the Boston Tea Party and take part in a reenactment of the “Destruction of the Tea.” Then, after all the fun, head to Abigail’s Tea Room & Terrace to enjoy some waterfront views of the city while sipping tea and enjoying some delicious treats from the bakery. My girls loved this experience because they got to toss the tea into the water, taste various teas and the gift shop was a big hit!

Shop at Faneuil Hall and Quincy Market while indulging in global cuisine at one of the many restaurants and pubs. Then, walk the promenade and enjoy some of the best street performances in town.

We did a self-guided walking tour through Harvard University in Cambridge, but you can also enjoy a student-led public tour to learn mysterious facts, hidden gems, and famous traditions. After walking the campus, we had lunch at Tatte’s. They have so many yummy sandwiches and sweet treats. I highly recommend the fig and prosciutto panini.

No Boston trip is complete without a visit to America’s most beloved ballpark and home of the Red Sox, Fenway Park. Take in the view from the Green Monster, formerly known as “The Wall,” which stands at 37 feet high.

A street view of one of Boston's main streets
Admiring Boston’s architecture at sundown.

On the last night of our stay, we hopped aboard the Old Town Trolley and went on the Ghosts and Gravestones Tour. We were treated to an evening of spooky stories and a tour of some of the city’s most haunted sites. One of my daughters was a bit hesitant, but we read the reviews and it seemed like a family-friendly tour. It turned out to be quite fun, and it was a great way to end our family vacation.

Best Bets for Food in Boston

Our favorite restaurant of the entire trip was Regina Pizzeria. It was recommended to me by a friend, and I’m so glad I listened. My youngest daughter usually has one slice of pizza, but she scarfed down three whole slices and then asked when we were coming back for more. There are a few Regina Pizzerias around the city, but make sure you visit the original on Thacher Street in the North End. It’s hands down the best pizza in town! If you’re in a hurry and just want a grab-and-go meal, then you can stop by one of their other locations.

If you prefer a more formal dining experience, reserve a table at Ocean Prime in the Seaport District. It’s a great place for surf and turf and a great walking neighborhood, too. I ordered the pork chops and lobster bisque and shared some of it with my daughter.

For an after-dinner treat, you must try the delicious Italian pastries in Boston. After stopping by a couple different places, we loved Bova’s Bakery in the North End. It’s open 24 hours and everything was fresh and delicious. This award-winning bakery has been family-owned and operated since 1926, and you can taste the love they put into every pastry and how they value their customers. Plus, it’s open 24 hours! Try the traditional Sicilian Cannolis, classic Tiramisu, and Lobster Tails. But I’m warning you: You’ll want to return before your trip is over.

Vanessa's family enjoying the snow
The girls’ first time in the snow!

Day Trips From Boston

I love how easily you can hop from one state to another in the New England region. If you’re planning to stay in Boston, it makes it easy to rent a car and take day trips to neighboring cities.

Vanessa's daughters in Kennebunkport, ME
The beautiful town of Kennebunkport.

Kennebunkport, Maine

I knew I wanted to return to Kennebunkport because I remember what a special place this was. It honestly feels like it’s straight out of a Hallmark movie. We passed picturesque towns on the way there, so the drive alone was worth it. Have your camera ready!

We spent the day strolling through town, sightseeing, shopping, and enjoying a lobster roll and lobster bisque at Alisson’s. If you’re a seafood fan, you can’t visit Maine and not have lobster!

Since we were there during winter, my girls got to see snow for the first time and were absolutely delighted to play in it and throw their first snowballs. We spent some time playing in the snow at a neighborhood park and then visited the Nubble Lighthouse in York before heading back to Boston for the night.

Vanessa and her daughters enjoying the winter weather
Snow tubing in Pats Peak.

Henniker, New Hampshire

Just an hour and a half away from Boston, you’ll find Pats Peak Ski Area in Henniker. The drive there is beautiful, and in the winter, you’ll see frozen lakes, snow-covered driveways, and icy roads. Drive safe! It was quite an adventure, but we reached Pats Peak and spent the afternoon snow tubing. It was amazing! We had an absolute blast, and we can’t wait to do it again. Now the girls want to take a skiing class!

We enjoyed a tasty seafood and prime rib dinner at Country Spirit Restaurant & Tavern in town before heading back to Boston. Reservations are recommended because the restaurant fills up quickly.

Cape Cod, Massachusetts

We also drove to Cape Cod. We visited Hyannis and saw the beaches, the Judah Baker Windmill, JFK Memorial, and had a late lunch at Captain Parker’s. Try their award-winning clam chowder!

We didn’t make it to the JFK Museum and the Whydah Pirate Museum, but they both look cool, so add those to your list.

These are just some of the highlights of our trip. We visited during the winter since we were in search of snow, but we’ve also been there in the fall and it’s breathtaking.

Happy travels!

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