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Jetsetter Guides

What to Do in Boston: The Perfect 3-Day Itinerary

Small town charm meets big city hustle in this New England capital. Boston is choc-a-block with historic landmarks, killer Italian eateries, topnotch shopping, and quaint cobblestoned streets. Here’s your ultimate weekend guide.

FRIDAY

Welcome to Beantown! Before you officially kick off the weekend, drop your bags at your hotel. There’s the brand-new Envoy, a cool-kid stay in the Seaport Innovation District, or the Fairmont Copley Plaza, an elegant grand dame across from Copley Square and Trinity Church. The former is best for those wanting a more modern design and incredible waterfront views (especially at the rooftop, which overlooks Boston Harbor), while the latter is a 1912 landmark that has hosted New England’s elite as well as a handful of U.S. Presidents in its gilded halls.

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Next stop: shopping. Browse the cute boutiques and gourmet grocery stores along Charles Street in Beacon Hill (while you’re here, peak down the picturesque old cobblestoned alleys), or flex that plastic at the upscale designer shops lining Back Bay’s Newbury Street. And when you need a pick-me-up, the Wired Puppy cafe is a local favorite. End the afternoon at Bodega, a hidden gem (literally). At first glance, the shop looks like your average convenience store—but if you step on a tile in front of the old Snapple machine in the back, a secret door will lead to a high-end shop selling sneakers and threads.

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In the evening, catch an al fresco show on one of the public lawns. We love the Free Friday Flicks, a summer event where you can pack a picnic and watch a free movie at the Hatch Shell amphitheater on the Charles River Esplanade. (Come early to see the sunset behind the sailboats and stone bridges.) Theater more your thing? Soak up some Shakespeare at a free performance at the Parkman Bandstand on Boston Common. This season, the play is the famous Romeo and Juliet (playing in July and August).

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Photo courtesy of Commonwealth Shakespeare Company

When hunger strikes, Publico is sure to satisfy. Don’t get discouraged by its location in “Southie” (formerly called South Boston, not to be confused with its adjacent neighborhood, the South End); this funky new restaurant sits on a super-safe stretch, just a 10-minute drive from the Envoy hotel. Opened earlier this spring, Publico has quickly gained a following for its charming courtyard garden, which has fire pits, a heated floor and a killer cocktail bar (order the French Ninja with Toki Japanese Whiskey, C. Drouin Calvados, Grenadine and Aguardiente Mist). Plus, the casual menu features snacks, small plates (the bacalao fritters are a must) and entrees that ring in under $20 each. Score!

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Photos by Brian Samuels

SATURDAY

Start the morning with a little sightseeing—because you can’t come all the way to Boston and not visit Faneuil Hall, the Paul Revere House and the Freedom Trail. The 2.5-mile walk starts in the North End (just follow the red brick path) and retraces the route of Paul Revere’s famous 1775 ride. Along the way, you’ll pass 16 landmarks, including the Bunker Hill Monument, Quincy Market, and the famous site of the Boston Massacre.

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And while you’re in the North End, we’d be remiss not to mention the neighborhood’s famous Italian restaurants and pastry places. Skip the line at Mike’s, and instead make a beeline for Bova’s Bakery. The family-run shop has been in business for three generations, making homemade cakes, cannolis, and cookies since 1932. Or, if you’re wanting more than just a tasty treat, take a cooking class at Christopher Kimball’s Milk Street—a multi-use venue that houses their magazine, culinary school and TV/radio studios, which you can also tour. Learn to whip up international plates (like the upcoming Thailand themed-course), take a wine-tasting lesson, and even master the art of recipe writing.

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Photos courtesy of CPK Media

There’s no better way to end the day than with some booze and views. Take a ferry from Seaport, Downtown or Charleston to ReelHouse, a just-opened waterfront restaurant in East Boston. Here, you’ll tuck into platters of fresh seafood (think: blackened swordfish tacos, a New England-style clam bake, Maine char-grilled lobster) while taking in the sweeping skyline.

SUNDAY

It’s Sunday, and you know what that means: brunch time, baby. The most epic spread can be found at Row 34, in the up-and-coming Seaport area. While it used to be known for its counter service, the restaurant has just released a full menu in 2017—and it’s to die for. We’re talking lemon and ricotta pancakes, smoked bluefish paté on a nori bagel, and the city’s best cup of clam chowder (IOHO).

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Photos courtesy of Row 34

Once you’re all fueled up, spend the afternoon getting cultured at two of Boston’s most impressive institutions. The Museum of Fine Arts (MFA, for short) is always packed with interesting exhibits, and this season is no different. Don’t miss Matisse in the Studio, which displays 36 paintings, 26 drawings, 11 bronzes and more by artist Henri Matisse alongside 39 works from his personal collection. Meanwhile, the more under-the-radar Isabella Stewart Gardner Museum is gorgeous not only because of its rare art and objects, but also for its striking architecture. Resembling a 15th-century Venetian Palace, the building centers around a tranquil open-air courtyard that feels like an oasis in the heart of the city.

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Top three photos (left ro right): Courtesy of Museom of Fine Arts, Boston and Musee Matisse/Museom of Fine Arts, Boston; Bottom photo courtesy of Isabella Stewart Gardner Museum

If sports are more your style, you’re in the right town. You won’t find a more devoted following than Boston Red Sox fans (sorry, Yankees!). Although most visitors will just snag tickets to the game, it’s worth it to go early—when you can see the players up close and personal. Three hours before the first pitch, you can take a batting practice tour that gives you behind-the-scenes access to Fenway Park and the Green Monster. Talk about bragging rights.

Toast to the end of your weekend at Terra. This restaurant is the latest addition to Eataly, the mega Italian market that debuted last year at the Prudential Center (lovingly called The Pru by locals). The sun-splashed space looks more like a greenhouse than a traditional trattoria, where plants line the walls and dangle from the massive glass ceiling. Plus, the food is just as ‘grammable as the decor. The menu focuses on barrel-aged beers and wood-fired Italian cuisine, including ricotta bruschette, housemade rabbit agnolotti pasta, and grilled quail with balsamic and honey.

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Photos courtesy of Eataly

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