How to Actually Enjoy Your Boston Layover

Turn an indirect flight into a mini-vacation.

By Hannah Lott-Schwartz

Boston is New England’s crown jewel and is rich with a national heritage rooted in history, the arts and, of course, athletics. Thanks to the city’s relatively small size, these attractions are all within quick access of Boston Logan International Airport, the region’s busiest hub, making Boston ideal for a long layover. Compact, walkable and simple to navigate, the city has a central downtown bordered by distinct neighborhoods that celebrate a range of legacies. You can take the free Massport Route 66 bus from any terminal to the water-taxi dock. Rowes Wharf Water Transport has a special ticket that includes round-trip water taxi fare from and to the airport plus luggage storage for the day. If you’re traveling light, follow signs to hop the Blue Line subway into the city. From there, take an à la carte approach to your ground time—based on how long each activity takes—to design a layover as snackable as the city itself.

If you have one hour or less…

In the North End (home to Boston’s Little Italy), locals spend summer days chatting while relaxing in the spindly-legged chairs that take over all but the tiniest sidewalks. Here you’ll be called upon to settle an age-old debate: Whose cannoli is best? Tourists swarm Mike’s Pastry (300 Hanover St.; 617-742-3050; mikespastry.com; dessert for two, $8), where treats are handed over in the store’s signature white box, tied neatly with string. Others swear by the old-world Italian recipes at Modern Pastry (257 Hanover St.; 617-523-3722; modernpastry.com; dessert for two, $7), whose brightly colored butter cookies are priced by the pound.

Stroll off the sweets by heading southwest toward the gold-domed Massachusetts State House—before it was gilded, Paul Revere covered the roof in copper—and Boston Common (139 Tremont St.; boston.gov), the nation’s oldest park. The Common’s carousel, reflecting pool and gorgeous flowers compete with the Public Garden (4 Charles St.; boston.gov), America’s first public botanical garden, and its collection of bronze statues across the road.

Sports fans may prefer to visit Fenway Park (4 Yawkey Way; 617-297-2000; fenwayboxoffice.com; tickets, from $18), the oldest stadium in the country. On game days, the surrounding streets fill with the cheers of Red Sox fans and the smell of grilled onions and Fenway Franks. To get close to the action without a ticket, duck into The Bleacher Bar (82A Lansdowne St.; 617-262-2424; bleacherbarboston.com; lunch for two, $25*), just below the center-field bleachers. The sports bar is open year-round and features a coveted ground-level nook with a view that puts you right in the outfield.

For a different perspective, head to the Prudential Tower, where 52 floors above the streets of Back Bay lies Top of the Hub (800 Boylston St.; 617-536-1775; topofthehub.net; lunch for two, $50). The restaurant affords one of the best views of the city. You can sit at the bar for a preflight beverage as you look out on the skyline to the east and Fenway Park to the west, while the Red Line zips across the Charles River, carrying commuters to Cambridge.

If you have one to two hours…

Yes, the puns are plentiful on a Boston Duck Tour (617-267-3825; bostonducktours.com; tours, $40 a person), but it’s not uncommon for a Harvard-educated guide to lead the 80-minute excursion aboard a WWII-style amphibious landing vehicle. Board at the Prudential Center, Museum of Science or New England Aquarium to learn about more than 30 Boston landmarks that define the city’s past and present.

An architectural masterpiece, the central branch of the Boston Public Library (700 Boylston St.; 617-536-5400; bpl.org) holds contemporary and ancient tomes, which you can discover on a free hour-long tour. Don’t miss the entrance hall—where Siena marble lions flank symmetrical bronze-lined staircases—and Bates Hall, a study with a 50-foot-high barrel-vaulted ceiling that runs more than 200 feet along the entire length of Copley Plaza.

To do a little shopping, visit SoWa Open Market (530 Harrison Ave.; sowaboston.com), in the South End, where more than 150 vendors peddle craft goods and art outdoors during summer weekends. Just inside the abutting warehouse, a massive vintage bazaar unfolds year-round. Boston memorabilia and letterpress blocks are sold alongside antique maps, clothes and trinkets.

If you have three hours or more…

One of the most comprehensive art collections in this part of the world is on view at the Museum of Fine Arts (465 Huntington Ave.; 617-267-9300; mfa.org; admission, $25). You could spend an entire afternoon browsing some of the nearly 500,000 pieces in its permanent collection before dipping into its celebrated gift shop. A different sort of art history lives at the nearby Isabella Stewart Gardner Museum (25 Evans Way; 617-566-1401; gardnermuseum.org; admission, $15), home to works by Rembrandt, Michelangelo, Manet, Degas and Sargent. The three-story, 15th-century-Venetian-style palace and its storybook courtyard were the site of a major unsolved art heist in 1990, a mystery that remains almost as well-known—and talked about—as the artists represented there today.

  • *Estimated meal prices do not include drinks, tax or tip.
  • NOTE: Information may have changed since publication. Please confirm key details before planning your trip.
  • Published: June 2017