The Perfect Three-Day Weekend in Boston
Travel + Leisure is exploring America one three-day weekend at a time. Here’s what to do on a short trip to Boston.
You can spend your entire life exploring Boston, one of New England’s most charming waterfront cities. But thanks to its compact—and completely walkable—downtown, it’s easy to see the highlights in a long weekend. This historic city has been reinventing its dining and hotel scene, with creative new restaurants and contemporary accommodations. Some of the best Bean Town attractions, like the gas-lit streets and Federal-style row homes, will never change. Before planning a vacation in Boston, check out this comprehensive itinerary.
Flying into Logan International Airport is the best way to get the lay of the land—and it’s only a $20 taxi ride from the Godfrey Hotel. This hotel recently opened in two meticulously restored landmark buildings just three minutes from Boston Common, in the Theater District.
Drop your bags off and take in the view from the floor-to-ceiling windows before heading to the Fort Point neighborhood less than a mile and a half away. Stop into Trillium Brewing Company to see what limited-edition beer they are offering that day. For dinner, dine on deviled crab toast, lettuce cups with crispy oysters, and a warm buttered lobster roll at Row 34.
Directly across the street is Barbara Lynch’s bar (appropriately-named Drink), where there is no cocktail menu. Tell the bartenders about your beverage preferences (think: herbal or sweet, cucumber or citrus) and let them flex their creative muscle while you nosh on the world’s most elegant crudité.
Related: Things to do in Boston
Jumpstart your day with a cup of cold brew and avocado toast (while now ubiquitous, this version is worth ordering) from George Howell Coffee located inside the Godfrey’s lobby.
Only a few blocks from your hotel is Brattle Street Bookshop, where you can browse vintage and rare books spread across three cozy floors. Owner Ken Gloss’ constantly changing collection includes gems like 100-year-old Baedeker travel guides.
For lunch, visit chef and owner Matthew Jennings’ meat-centric Townsman. Highlights include the braised pork shank and the BBQ duck leg, best paired with a rotating cocktail on tap. After your afternoon in Downtown Crossing, stroll through Boston Common: the oldest city park in the country. The Common opens up into the Public Garden, where Swan Boats have pedaled across the willow-fringed lagoon since 1877. If you need something a bit more intense, Boston abounds with local fitness studios. You can easily squeeze in a 45-minute spin class at Recycle on Newbury Street, which is just beyond the Garden.
Finish the day with dirty martinis and serious cuts of meat at the intimate Bogey’s Place, a hidden room inside J.M Curley with a distinct Prohibition-era feeling. When you’re ready to bed down, you’ll happily find yourself around the corner from the Godfrey.
Grab an almond croissant at Tatte Bakery in Beacon Hill (only a 10-minute walk through Boston Common) before hopping into a cab for the 5.5-mile ride to one of the city’s lesser-known attractions: the 265-acre Arnold Arboretum of Harvard University, designed by Frederick Law Olmsted. The all-season park offers paved paths for easy walking, forested areas for light hiking, and vast seasonal gardens. Come October, enjoy a free, guided walking tour on weekends and learn all about the vibrant foliage.
On the way back from the Arboretum, stop by new Greek concept Saloniki, which sits in the shadow of Fenway Park. Pitas like The Herc with braised pork shoulder, or The Despena with zucchini-feta fritters, will keep you full until dinner. Afterward, take a comprehensive, hour-long tour of Fenway Park (tickets only available at the box office, $18) or stop by the Isabella Stewart Gardner Museum for a look at Renaissance paintings in an Italianate home (the courtyard alone is worth the $15 ticket price). For dinner, don’t miss Chef Jody Adams' Mediterranean restaurant, Porto, in the Back Bay. Her fans were devastated when Adams closed her beloved spot, Rialto, in Cambridge, but rejoiced when she opened a new kitchen across the Charles River. Order the tomato salad with yogurt and honey and the squid ink bucatini.
End the evening—and your perfect Boston trip—at Yvonne’s, the swanky lounge and restaurant in the space of the former Locke-Ober (where President Kennedy was known to entertain foreign heads of state). There’s no better place to nurse a nightcap than at the original mahogany bar, carved on site in 1886. If you’re still hungry, order the cognac and espresso soaked “twinkie” filled with ricotta cannoli filling and covered in a hard chocolate shell.
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