Boston: A Local's Travel Guide
I lived in Boston for nine years, in Somerville, Cambridge, Waltham, and Back Bay, so this one is close to my heart. It is a walkable, red-brick city of history, harbor views, and college energy, and here is the Boston I actually know.
Where to stay
For a weekend, I would stay in the North End, Boston’s Little Italy, all charm and incredible food, or in Back Bay, elegant, central, and walkable to almost everything.
History and the classics on foot
Walk the Freedom Trail (you can do it yourself, just download the app for the history), stroll the Public Garden to find the Make Way for Ducklings statues, walk the Charles River Esplanade, and do the classic Duck Boat tour. For a fun afternoon, tour the Harpoon Brewery, one of many great microbreweries in the city.
The museums
My most-repeated were the Isabella Stewart Gardner Museum and the Museum of Fine Arts. The Museum of Science has amazing rotating exhibits, and I loved the New England Aquarium, especially its after-hours cocktail evenings. There is a lot here, so see my Boston museums guide.
Where I actually eat
Boston’s food scene is seriously good. My top three anywhere are Yvonne’s, Sorellina, and Trattoria Il Panino. Downtown: Yvonne’s and Mooo. North End: Trattoria Il Panino. Back Bay: Sorellina, Contessa, Lolita, and Abe & Louie’s. Seaport: Empire and the Envoy rooftop (drinks). South End: Barcelona (there is one in Brookline too). Near Harvard: Beat Brasserie. And Tatte Bakery is everywhere and always worth it.
Day trips and when to go
Boston is the gateway to New England. Build in a day trip, Cape Cod, Martha’s Vineyard, Provincetown, or Salem, in my Boston day trips guide. Fall is spectacular for the foliage; spring and summer are lovely on the water. I plan it all, in English or Español.
Here is where Boston gets tricky. The tables worth traveling for book weeks out, and the whole city tightens around the marathon, graduation season, and peak foliage weekends, when rooms are scarce and rates jump. Booking it blind is how a good trip turns into a scramble, so I lock the reservations and the timing so your days actually flow.