Quirky, under-the-radar highlights only a local could recommend.
Often missed by tourists and locals alike, Castle Island in South Boston is a great place to stroll along Boston Harbor. The site of an old armory, it is a 22-acre “land-bound” island (meaning it was connected to the mainland by a narrow strip of land in 1928) home to a paved walkway and a shoreline string of parks and beaches. Bring a picnic, or hit the snack bar that serves burgers, fries, clam strips, and ice cream.
BUNKER HILL MONUMENT
Boston is a city filled with landmarks, but one of the less touristy spots is this 221-foot-tall granite obelisk in Charlestown that marks the site of the first major battle of the American Revolution. While you can hoof the 294 steps to the top to see the unparalleled view of the city, locals prefer to sprawl out on the lush green lawn to soak up the sun with a picnic or dive into a book.
Roped off behind the bar of JM Curley in Downtown Crossing, this secluded, darkly lit 20-seat chophouse is marked only by a small gold placard that reads “Bogies” and the art deco signage that proclaims “Adults only. Please no cell phone use.” Inside, expect decadent cuts of steak, caviar service, and à la carte build-your-own martini menu.
One of Boston’s oldest restaurants, having opened in 1885, this local gem on a dead-end street in Downtown Crossing features a comfort food menu that takes cues from French, Italian, and straight-up New England. Locals swear its “Sunday Gravy” is the best pasta dish you’ll get in all of Boston.
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6 p.m. | Twirl around the Ice
If you want to feel like you're bringing a Currier & Ives print to life, head to the seasonal ice rink at Frog Pond on Boston Common, rent some ice skates, and twirl around the ice skating rink. A "life is good!" feeling will sweep over you. To try out Boston's newest skating venue, visit the huge ice skating path at City Hall Plaza. The whole area transforms into a winter paradise, complete with places to eat and drink, and even a European-style Holiday Market where vendors and artisans offer specialty products.
10 a.m. | Dinner at Beacon Hill Cheers
Originally founded as the Bull & Finch pub in 1969, this late-night restaurant has now adopted the name for the show it inspired back in the 1980s: Cheers. While the show itself wasn’t filmed here, the producers modeled its Hollywood version off it and showcased the iconic facade in the opening credits. Naturally, the menu pays tribute to the characters with names like Carla’s Meatballs & Linguini and the Norm Burger.
10 a.m. | Walk the Freedom Trail
Starting at Boston Common, the two-and-a-half-mile self-guided Freedom Trail wends its way through 16 Revolutionary Era sites, from the Boston Massacre in front of the Old State House to the Paul Revere House in the North End. The walk can take all day if you plan to stop and tour every site, so we suggest first perusing the full map and keeping your stroll focused to just your favorites.
1 p.m. | Lunch at the Butcher Shop
Inspired by the chef’s travels throughout France and Italy, this tribute to European boucheries in the South End is both a neighborhood wine bar and full-service butcher shop. Enjoy a glass of wine along with handmade charcuterie, antipasti, and bistro-inspired dishes.
3 p.m. | Isabella Stewart Gardner Museum
If you’re wearing Red Sox memorabilia, you receive discounted admission to this Fenway-Kenmore museum that houses philanthropist Isabella Gardner’s eccentric art collection. As you peruse the collection, note the handful of empty frames. It’s not a mistake but a sad reminder of the US’s biggest art heist that whisked away 13 masterpieces more than 25 years ago, including a Rembrandt, a Vermeer, and a Manet.
8 p.m. | Dinner at Lucky’s Lounge
Descending the stairs into this Frank Sinatra–themed bar is like stepping through a portal into a swinging hipster lounge straight out of the ’50s. Every Saturday night, from 7 to 10 p.m., a tribute jazz band covers the best of Old Blue Eyes.
10 a.m. | Brunch at Boston Chops
You might not think of a steak house when you think of brunch, but this South End restaurant will make you think twice. Expect steak house staples with a twist, like shank and grilled tongue hash, beef tournedo and eggs, and huevos rancheros with machaca beef cheeks.
12 p.m. | Visit the Museum of Fine Arts (MFA)
This venerable Boston institution is the fourth largest museum in the United States, containing more than 450,000 works of art, from ancient Egyptian to contemporary. On display through June 2017, you can see more than 50 works by Robert McCloskey, the beloved author and children’s book illustrator who penned the Boston-based Make Way for Ducklings.
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This South End gourmet food shop specializes in small-production artisan cheeses, charcuterie, handmade sweets, hard-to-find spices, and more. It also features culinary programs, from introductory cheese tastings to demonstrations with local chefs highlighting Formaggio products.
Come spring and summer, this behemoth of a farmers’ market pops up in the South End. Essentially, several markets – a farmers’ market, an arts market, a vintage market, and a food truck market – are all rolled into one in this Sunday event that draws thousands of visitors from across New England. To step things up in 2016, SoWa even premiered Boston’s only weekly beer and wine garden.
This little taste of genuine Italy is tucked away between a narrow alley in the North End. In addition to being a grocer of homemade pastas, breads, and imported goods, like mozzarella and other cured meats, it’s probably best known for its made-to-order sandwiches the size of your forearm. Try the panino – prosciutto and freshly made mozzarella with tons of olive oil on thick crusty bread.
This South Natick business is owned by a Cambridge School of Culinary Arts grad, who creates from-scratch flavors of gelato and sorbet with milk and cream from local dairies and fruit and nuts sourced locally when possible. While you can find the frozen treats in restaurants, like Strega Waterfront, be on the lookout for a frozen dessert truck one day.
Open May through November on Tuesdays and Fridays, Boston’s biggest and busiest farmers’ market is in the heart of Back Bay’s commercial and cultural hub. More than two dozen Massachusetts farmers offer a vibrant selection of local and delicious products, selling fresh-baked bread, cheese, pasta, hummus, fresh-caught fish, and more.
When simply “seeing” a destination just won’t do.
One- and two-hour tours start at the State Street location, then wend through the center of the city, passing landmarks, like the Financial District, the Harborside, and R.F. Kennedy Greenway.
Rent kayaks, canoes, and stand-up paddleboards, and take on the nine-mile stretch of the Charles, which virtually has no current, allowing for painless round-trips. Home to the world’s largest rowing regatta, Head of the Charles, the river winds past scores of parkland, local colleges, like Harvard and MIT, and the Esplanade.
The 40,000-square-foot facility feels like a community center mated with a rock climbing gym. In addition to 28,000 square feet of climbing space, the space is adorned in local art and murals and features lounges and space for community events.