Curator’s statement
Boston is a lifestyle, not just a destination. When I arrive in Boston, I feel like a completely different person—in the best way possible. The neighborhoods, the food, the sports—this city is a vibe in itself. I love Boston because it’s full of history, architecture, and cobbled streets—and it’s right on the water. It has everything you could want in a city.
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Things to do in Boston
Catch a game at Fenway Park.
Head to Fenway Park for a game—or at least the Bleacher Bar for a cocktail, some history, and the most amazing views.
Wander Little Italy and the North End. I always find the best Italian bakeries and coffee shops here.
For us history nerds, walking the Freedom Trail is a must. The Trail starts in Boston Common—make sure to hit the Paul Revere House, too. If you have the time to walk the 2.5 miles. You’ll see historic houses, museums, and churches—there’s nothing else quite like it.
I’m also a book enthusiast, so when I make my way to Boston, I love stopping by the Boston Library—it’s so beautiful. On a nice fall day, I can’t help but grab a coffee, wander the grounds of Harvard, and stop at Brattle Book Shop or Beacon Hill Books & Cafe on my way to lunch.
The Isabella Stewart Gardner Museum is a work of art all its own, especially the courtyard and gardens. The museum has seasonal exhibits, so any time of year, you’ll be sure to see something new. If you want to get out on the water, you should jump on a catamaran and go whale-watching or get in a kayak and see the city from a different perspective.
If you’re in Boston in the fall, you should join a Fall Foliage Brunch Cruise with Classic Harbor Line Boston. Cruise out to the Boston Harbor and take in the skyline, nature, and colors—it’s a fall dream. Enjoy a beautiful brunch buffet afterward, complete with apple cider mimosas or an “Apple-rol Spritz.” Enjoy the festive decor in the most relaxing atmosphere.
Places to eat & drink in Boston
Don't miss a lobster roll while in New England!
Faneuil Hall Market is a must. If you’ve never been, it’s a historic building with so much charm. You’ll find grocers, bakeries, food stalls, restaurants, and shops.
Omni Parker House for the best Boston cream pie (where it originated) or Union Square Donuts for the perfect donut version.
Bricco Panetteria for fresh sfogliatelle and Italian sandwiches. Be sure to look through their grocery store and snag some must-have Italian olive oil, cheeses, vinegars, red sauce, and salami that’s hung from the ceiling.
Thinking Cup or Polcari’s Coffee for a great cup of joe! Like I said, grab a cup to go and wander Beacon Hill in the crisp air, or stay and take in the old-school charm of the buildings—you can’t go wrong with either.
Stillwater Boston for reimagined comfort food, especially when you need to warm up and feel cozy.
1928 Boston for classy, speakeasy vibes in the picturesque Beacon Hill neighborhood. It serves classic but high-end American fare.
Mare Oyster Bar with its back patio, fire pits, and extensive seafood menu—and of course the oysters!
Luke’s Lobster at Boston Harbor for a classic lobster roll done Luke’s way: with a bit of mayo and a spritz of lemon butter.
Need to know
Best time to visit: the actual truth
Fall is king. September through mid-October is pure magic—perfect weather, foliage, and no snow slush in the streets.
Avoid March. It’s a dirty, gray, frozen slush pile. We call it “fake spring”—don’t fall for it.
Winter holidays are worth it if you can handle the cold. Beacon Hill, with its wreaths and gas lamps, is straight out of a movie.
Photo ops locals actually approve of
Acorn Street in the early morning before it’s swarmed.
The Charles River Esplanade at golden hour.
The Boston Public Library courtyard—especially if it’s raining.
Insider tips for passing as a local
Rooftop at Legal Harborside in the Seaport for sunset drinks.
If you want cheap Fenway tickets, buy “standing room only” and move into empty seats after the third inning.
You can walk the Freedom Trail, but break it up into two days so you can eat and wander without rushing.
The best view of the city is actually free. Take the elevator up to the Cambridge Marriott lobby, then sneak up to the higher floors for skyline photos.
Travel Advisor
Alexana Rotunda
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