Canada & New England · Destinations
July 24, 2020 Words: Frances Thomas

3 Days in Boston

Lovers of American history will do well to put Boston very high on their to-visit list. Here’s how to enjoy its most iconic spots — and a few hidden gems, too — in 72 hours.


Founded nearly four centuries ago by Puritans from England, Boston is one of the oldest cities in America. Home to the nation’s first public park, public school, municipal library, and subway system, it is widely regarded as “the cradle of modern America,” a cornerstone of U.S. patriotic identity, and a mecca for history buffs. But there is more to Boston than its historical status, from a thriving culinary scene to a panoply of cultural sites, shopping destinations, and urban architecture. Compact and easily navigable by foot, the city is perfectly laid out for a long weekend of sightseeing.

Day One – Freedom Trail, Back Bay, and North End

There’s no better way to start your trip than a walk along the Freedom Trail, the iconic 2.5-mile path through 16 historic national sites. Begin at Boston Common and make your way through a collection of legendary museums, churches, meeting houses, burial grounds, parks, and other landmarks dating to the American Revolution. Near the start of the trail, make sure to dip inside Brattle Book Shop, a sprawling used book store dating to 1825 with over 250,000 books, postcards, maps, and prints. When you get hungry, stop at Faneuil Hall, the site of America’s first Town Meeting and now a bustling marketplace with a food court, stand-alone kiosks, and sit-down restaurants.

After crossing the Freedom Trail finish line, meander over to Back Bay, a waterfront enclave known for dining, designer stores, and picturesque single-family brownstones. For shopping, explore Newbury Street, a glitzy boulevard dotted with upscale fashion boutiques and independent storefronts. If you’re itching for more history, head to Copley Square, a popular green space flanked by the Boston Public Library and Trinity Church, the city’s first feat of Romanesque architecture, dating to the 19th century. As the afternoon winds down, walk a few blocks northeast from Copley Square to Cheers, the real-life pub that inspired the NBC sitcom of the same name. Though the interior is a lot smaller than it appears in the show, the exterior facade — the establishing shot of every episode — is the exact same.

For dinner, make your way to the North End, also known as Boston’s Little Italy, to feast on pizza, pasta, and cannoli. Seafood fans should head to The Daily Catch, a Sicilian-style eatery famous for its calamari meatballs; for a more old-school Italian meal, you can’t go wrong with Prezza. No matter where you have dinner, dessert has to be at Mike’s Pastry, a veritable Boston institution known for its extra-large cannolis.

Day Two – Museum-Hopping and Fenway Park

Ask any Bostonian for art museum recommendations, and chances are, they’ll rattle off an impressive — and overwhelming — list of options. You can’t see them all over a long weekend, but luckily, two of the best are in walking distance of each other: the Isabella Stewart Gardner Museum and the Museum of Fine Arts (MFA). Start at the former, set inside a Venetian-inspired palazzo, to behold the personal collection of its eponymous founder, an eccentric socialite who dedicated her life to accumulating art by masters like Botticelli, Titian, and Raphael. After an hour or two, head to the MFA, a vast gallery with over 500,000 pieces from around the globe, including some of the country’s finest Japanese, Egyptian, and of course, American works. Pro tip: before you start exploring the wings, have lunch inside the museum at 465 Bar and Restaurant, one of the city’s top spots for seasonal New England fare.

After a morning (and likely afternoon) full of museum-hopping, switch gears and head to Fenway Park to celebrate America’s favorite pastime. If you’re visiting during the baseball season, make sure to see a Red Sox game; if not, the sprawling grounds of the park are worth exploring in their own right. Whether or not you book a guided tour, make sure to stroll down Jersey Street, famous for a two-block-long row of World Series Champion banners donning the Red Sox logo. For dinner, avoid the spots in the park crowded with tourists and walk a few minutes north to Island Creek Oyster Bar, a locals’ favorite for fresh-off-the-dock oysters and inventive small plates.

Day Three – Beacon Hill, Rose Kennedy Greenway, and Seaport District

Spend your final morning in Beacon Hill, arguably Boston’s most picturesque neighborhood. From the iconic cobblestones of Acorn Street to the Federal architecture of Louisburg Square, there is no shortage of quaint corners from a bygone past to explore. Window-shop on Charles Street, the city’s five-block epicenter for independent boutiques, and stop in one of the many cozy cafés for coffee and pastries.

Walk south along Charles Street until you hit Boston Public Garden, the first public botanical garden in America, at the base of Beacon Hill. If you’re visiting in the spring or summer, ride a foot-propelled Swan Boat in the lagoon; if it’s wintertime, ice skate along the frozen-over Frog Pond in nearby Boston Common.

After the garden, walk through Chinatown to the southern end of the Rose Kennedy Greenway, an urban park edging along 1.5 miles of the waterfront. Explore the public art installations, indulge in the local food trucks, and take a ride on the Greenway Carousel.

In the nearby Seaport District, don’t miss the Boston Tea Party Ships & Museum, a replica of one of the ships from which the Boston Tea Party protests took place in 1773. In this immersive floating museum, watch live actors reenact the monumental Tea Party events and toss tea into the barge alongside them.

Toast your 72 hours in Boston at Harpoon Brewery & Beer Hall, a famous craft brewery at the southern end of the Seaport District. Your trip wouldn’t be complete without a Boston lobster roll, so finish off the day at Yankee Lobster, a famed seafood shack right next to Harpoon with waterfront views.

Boston, Waterfront, Dusk, Skyline
Boston, Autumn, Foliage, Skyline
Boston, Foliage, Fall, Park


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