Best Things to Do in Boston, From Local of 18 Years

When in Boston, I recommend doing as the Bostonians do and finding an Irish pub to nurse a pint or two in.

There’s no shortage of options, but some of my go-to’s are Mr. Dooley’s, where lots of Irish transplants post up for a Guinness that tastes like home, and J.J. Foley’s, Boston’s oldest Irish pub.

The city’s North End is largely considered Boston’s Little Italy. Most tourists usually flock to Regina Pizzeria, which has a great pie. However, I actually prefer the pizza at Quattro, which is right around the corner.

This contemporary pizzeria serves Neopolitan-style pies cooked in an authentic wood-burning oven from Naples, Italy.

When I took an Italian friend there, they were impressed by the fresh, high-quality ingredients and the nice char on the crispy yet tender crust.

When most people think of Boston beer, the first brand that probably comes to mind is Sam Adams. In my mind, though, since Sam Adams brews are available at bars all over the country, you’re better off trying something you can’t find back home.

Instead, I recommend checking out Aeronaut Brewing Company, located in nearby Somerville, Massachusetts. You can easily spend a whole night playing arcade games, listening to live music, and sipping tasty drinks.

If beer’s not your thing, don’t sleep on the distilleries. Boston may be known for its beer, but there are also lots of really impressive spirits producers, including GrandTen Distilling and Bully Boy Distillers.

Most tourists make it a point to get a bowl of chowder while they’re in town, and although there’s nothing wrong with this move, I think oysters should be on everyone’s itinerary.

In my opinion, even if you’ve tried them before and couldn’t get on board, you can’t say you’re not a fan until you’ve tried some freshly shucked local oysters.

Honestly, I used to think they were gross until I gave them another shot at Row 34. The restaurant has an unparalleled raw bar with a variety of local oysters to choose from — not to mention killer wine and beer pairings and some crave-worthy fried seafood to boot.

If you’re visiting Boston in the warmer months, I highly recommend grabbing some takeout and having a picnic along the Charles River Esplanade.

This green space offers a beautiful view of Cambridge, the Longfellow Bridge, and, if you’re lucky, a few sailboats.

Berklee College of Music is considered one of the best music schools in the world. So, it should come as no surprise that Boston is brimming with talented musicians.

I love checking out local talent at places like The Red Room at Cafe 939, Loretta’s Last Call, and The Beehive.

If you’re a big music fan, consider planning your trip in May during the Boston Calling music festival. It may not get as much hype as Coachella or Lollapalooza, but it’s attracted some major acts in recent years — from Ed Sheeran and The Killers to Chappell Roan and Noah Kahan.

A library might not be the most obvious pitstop when you’re on vacation, but trust me — the Boston Public Library is worth a visit.

Visit the stunning open-air courtyard, peruse the ever-changing art and history exhibits, take a tour, or have a drink in the elegant Courtyard Tea Room.

This story was originally published on February 21, 2025, and most recently updated on June 9, 2025.