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Boston is a city rich with more than 250 years of American history, but it is no place for reverence. The anti-British spy networks that helped spark a revolution here were radicals and resisters, and today their city remains boldly alive with ideas and activity. Some destinations are for unplugging; this one is for plugging in.
The harborfront city is beautiful, safe, and packed with sports and concerts all year, but the warmer summer and fall months are an ideal time to visit, with Sail Boston’s tall ships, Fenway Park concerts, the North End Feasts, the Boston Film Festival, and October’s Head of the Charles Regatta filling the calendar this year. Ariana Grande, Kacey Musgraves, and Charli XCX are all headed to TD Garden, just a few minutes’ walk from the revolutionary epicenter in the North End.
I visited recently with my family over a long weekend of exploring, shopping, and college scouting. Our base at Four Seasons Hotel Boston had an address facing the Boston Public Garden, so our first stop was a nostalgic pilgrimage to see the Swan Boats and ducklings immortalized by children’s book author Robert McCloskey. Then it was on to the high-end shops of Newbury Street, brunch in Beacon Hill, and literal gallons of Dunkin’ iced coffee. Here are some of our recommendations for what to do and where to eat, drink, and stay on your own trip to Boston.
What to See
The Freedom Trail
Obvious but unmissable: a 2.5-mile walk on the Freedom Trail, with 16 historic points of interest beginning at grassy Boston Common and including Faneuil Hall, once the city’s leading public meeting hall and now the anchor of a busy marketplace and food hall. Learn about figures as disparate as John Hancock (the Patriots’ money guy), Sam Adams (master of political messaging), and Crispus Attucks, the dockworker of African and Native American ancestry who became one of the first martyrs to the Patriot cause. Hub Town Tours also offers walks through Back Bay, focused on the city’s role in the women’s suffrage movement, and along the Black Heritage Trail in Beacon Hill, which marks key sites in the fight to end legalized slavery.
Harvard Square
You don’t have to go to “a school just outside of Boston” to enjoy a day in this eclectic Cambridge neighborhood full of shops, cafés, and coffee houses near the campus of Harvard University. Literary types will want to browse the famed independent Harvard Book Store, Rodney’s for used books and posters, and Grolier Poetry—a poetry-only bookshop that will impress any date. And don’t overlook the Harvard Art Museums, where the collection is world class but admission is free. The café in its sunny center courtyard makes for a lovely coffee break.
SoWa Art + Design District
The once-empty warehouses of this neighborhood in Boston’s South End have gotten a glow-up in recent years thanks to local creatives. At the SoWa Open Market, Sundays from May through October, the streets fill with artists, vintage dealers, food trucks, and farmers. Come back on the first Friday of the month to browse galleries, meet artists in their studios, and shop for ceramics, jewelry, and artwork directly from the people who made them.
Where to Eat
Contessa
Conceived in maximalist fashion by Ken Fulk, this rooftop trattoria has been one of Boston’s toughest reservations since opening in 2021. The Northern Italian menu is as decadent as the décor, including spicy lobster capellini and a Tuscan bistecca Fiorentina meant for sharing. Overlooking Back Bay and the Boston Public Garden, Contessa is also an appealing option for brunch or a late-night glass of Super Tuscan.
1928 Beacon Hill
Owner Kristin Jenkins, an antiques dealer, poured her sense of style and of history into this clubby, locally beloved restaurant. Choose from four themed dining rooms (The Library is a favorite) serving truffle deviled eggs, New England seafood, and an elite burger. A sister restaurant, 1928 Rowes Wharf, has a waterfront patio overlooking Boston Harbor.
Saltie Girl
You’re in New England—don’t leave without having a lobster roll. Enjoy one at Saltie Girl along with oysters and caviar from the raw bar and a cold glass of champagne. For sardine heads, this restaurant also has one of the largest tinned-fish collections in the country. Follow up with shopping on Newbury Street for a picture-perfect Boston afternoon.
Where to Drink
Lou’s
Our family loved Lou’s, a 1-year-old Cambridge jazz club where you can hear live music of many genres, including R&B, reggae, and Latin swing. For a subterranean room filled with velvet booths and low lighting, the service is surprisingly neighborhood-friendly, and the bar concocts fun mocktails like the Figgie Smalls, a mix of salted fig cordial, lemon, and ginger beer. After 10 P.M., the crowd is restricted to 21-plus.
Courtyard Tea Room
For one of the city’s most elegant tea services, head to the Boston Public Library’s main branch on Copley Square. Wear your garden-party finest to enjoy bites like lemon poppy seed scones with lemon curd, blueberry jam, and Devonshire cream. Sipping in the stacks is a tradition in bookish Boston: Folio, the lounge in the Boston Athenaeum library and museum, and Beacon Hill Books & Café, a bookstagrammer’s dream of a coffee spot, are also well worth a visit.
89 Charles
With its brick sidewalks and glowing gas lamps, Beacon Hill becomes wildly romantic after dark. End your evening with a nightcap at this speakeasy, down a few steps and behind a barely marked door. Opened in September 2025, the Gatsby-esque cocktail bar specializes in an array of playful martinis, from lychee to hot ’n’ filthy.
Where to Stay
Four Seasons Hotel Boston
We knew we were in great hands at the Four Seasons Hotel Boston when the reception desk staff welcomed our dog by name as she—er, we—checked in. Convivial service and thoughtful touches continued throughout our stay; we looked forward to dropping by the complimentary barista bar each morning and drinking our lattes on a walk around the Public Garden. The lobby-level areas—reimagined by Ken Fulk to evoke the residential salons of Back Bay and Beacon Hill row houses—may be the prettiest in Boston. And though the Royal Suite is pictured here, our Garden-View Executive Suite was exceedingly comfortable, with cozy couches and treetop views. Families will feel spoiled by the pantries stocked with free candy and snacks, an indoor pool on the eighth floor, private college tours for teens, and unlimited treats for your fur baby.
The Charles Hotel
If Boston is the Hub of the Universe, The Charles might be its center of gravity. A stately but not snobby presence on Harvard Square, the hotel has long hosted visiting professors, families of students, and dignitaries like the Dalai Lama (not to mention Boston royalty Ben Affleck). Music fans pack the resident jazz club, Regattabar, and there’s an array of new suites, some with fireplaces and four-poster beds. You’ll know you’re in Massachusetts by the Shaker furniture, leather wing chairs, and framed quilts lining the lobby walls.
Mandarin Oriental, Boston
The spa’s the draw at this luxurious hotel in Back Bay. Its therapists are skilled in a long list of holistic treatments informed by traditional Chinese medicine; the signature Time Ritual allows you to book a 110-minute slot for the spa to customize a therapy to your needs. The hotel rooms share the serene, tasteful vibes Mandarin Oriental is known for, and the location—near the Prudential Center and Copley Square—is central to just about everything.
