Boston is fondly known as America’s biggest small town, and it’s easy to see why: charming, cobblestone streets, flowering green spaces, and a thriving food scene that stretches far beyond downtown have helped turn this quiet New England city into a travel-worthy destination.
For the best views of Boston, take a ferry out to the Boston Harbor Islands. Here, you can explore a Civil War-era fortress and snap postcard-worthy shots of downtown Boston’s skyline.
Later, check out the highly underrated Isabella Stewart Gardner Museum. The beautiful, 15th-century Venetian-style house-turned-museum boasts galleries (containing John Singer Sargent, Rembrandt, and Fra Angelico, to name a few) and a flowering courtyard.
The museum isn’t far from Fenway Park, one of the most recognizable Boston landmarks. It’s been the home of the Red Sox since 1912, and even non-baseball fans will enjoy a game or a guided tour. Toast the home team later at The Hawthorne bar, tucked beneath the Hotel Commonwealth, or marvel at the impressive in-house wine collection at Deuxave.
Fun things to do in Boston continue on the other side of the Charles River. Take the Red Line T to Harvard Square, a bustling part of Cambridge that features many shops and restaurants, as well as the namesake university. The manicured grounds are perfect for sunset strolls.
Harvard Square also has a lively jazz scene: catch a show at Regattabar, in the Charles Hotel. It’s not uncommon to hear a Jobim tribute.
What to do in Boston if you want to stretch your legs? Take a walk, run, or bike ride along the three-mile Charles River Esplanade. The green space is full of marshes and playgrounds, and is the perfect spot to rent a sailboat on a balmy summer day.
Don’t confine yourself just to downtown. Some of the best Boston attractions can be found in artsy Jamaica Plain, where restaurants served cuisine from around the world. Think: Cuban, Scottish, and Cambodian fare. And for the best Italian food outside of Italy? Try the North End.