Boston is a city steeped in history.
It’s also one with prolific natural beauty, unwavering pride in its sports teams and a whole selection of renowned museums. Boston baked beans that once filled sailors and merchants may have earned the city the nickname Beantown, but these days you can expect much more on your plate. Here you’ll find a flourishing dining scene, where some of the best seafood in the US is served alongside enticing global dishes.
There’s an endless list of to-dos in the largest city of the Commonwealth of Massachusetts. Here are 11 of the very best experiences to help you plan your visit.
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The legendary USS Constitution has never gone down in battle © cdrin / Shutterstock
1. Walk the Freedom Trail with a guide or at your own pace
The Freedom Trail is a 2.5-mile walk through the city that leads past 16 colonial and revolutionary historical sites, and it’s one of the city’s most popular visitor attractions. Stops include the Boston Common (the city’s main green space), the golden-domed Massachusetts State House, Faneuil Hall, Paul Revere House, the warship USS Constitution and Bunker Hill Monument.
Planning tip: There are group tours that lead you along the Freedom Trail, with guides in 18th-century costumes. You can also do it yourself – just download a map from the Freedom Trail website and follow the bricks on the sidewalk. A self-guided tour allows you to go at your own pace, giving you the flexibility to stop at Faneuil Hall to munch through a few of the local food stalls, or to book a supplementary tour aboard the USS Constitution. You can even split the trail up over several days to make the most out of each of the Boston neighborhoods it winds through.
2. Surround yourself with culture at Boston’s Museums
There’s a museum for just about every taste in Boston. If fine arts is your jam, there are paintings, sculptures and tapestries at the Isabella Stewart Gardener, while the sprawling MFA features more than 450,000 works of art. For more targeted collections, there’s the Institute of Contemporary Art, the Museum of Science, the Boston Children’s Museum and the ever-popular fish-filled New England Aquarium.
Beacon Hill is a particularly charming Boston neighborhood to wander around © Albert Pego / Shutterstock
3. Explore Boston’s distinct neighborhoods
Each of Boston’s various neighborhoods displays its own personality and unique allure. There are technically 23 designated neighborhoods but a few of the most noteworthy include the South End, known for its brownstones and multitude of restaurants; Back Bay, where the long Commonwealth Avenue Mall is a year-round highlight of trees, park benches and statues; the newly developed Seaport where highrises are juxtaposed against the harborfront walk; and the North End, otherwise known as “Little Italy.” There’s also South Boston, which used to be known for its Irish-American culture but is now a young professional’s playground with lots of bars and restaurants; not to mention Fenway-Kenmore, Chinatown, the downtown financial and theater district, and charming Beacon Hill.
Planning tip: Dedicate a few mealtimes to the North End – there’s simply too much to eat and drink here for one visit. Hanover Street can be touristy but being part of the crowd is part of the experience to fully enjoy the authentic pizzerias, salumerias, coffeehouses and pastry shops (try the cannoli at both Mike’s Pastry and Modern’s to weigh-in on the longstanding local debate of who makes them better).
4. Drink a craft beer (or two)
In 1984, Samuel Adams revived the craft beer scene when it released its Boston Lager, “the full-flavored beer they deserved,” says the brand. Today, the local brewery still pours its iconic beer at two taprooms in the city, while also offering rotating seasonal brews and tasting flights. Use Samuel Adams as a starting point in a craft beer tour, then try some of the other local craft brands that have followed, like Night Shift, Trillium, Harpoon, Jack’s Abby and Cisco.
Local tip: If you’re visiting in the late spring, summer or early fall, look for popup beer gardens from the aforementioned brands that take advantage of Boston’s riverside, public gardens and harborfront. The scenery complements the signature and seasonal beers – sipping a fruity roast under the summer sun or enjoying an Oktoberfest among crunchy autumn leaves.
Share the local enthusiasm for sports by going to a game or watching one in a bar © Joy Brown / Shutterstock
5. Catch a game at Boston’s famed stadiums and parks
Boston is a sports city, and whether or not you’re a sports fan, the city’s commitment to its home teams is contagious. Fenway is a great place to start; opened in 1912, it’s the oldest ballpark in Major League Baseball. There’s also TD Garden, home to the Celtics, Bruins and mainstream concerts. Gillette Stadium is about 27 miles away, but worth the trip for a Sunday tailgate before watching the Patriots play.
Local tip: If you missed out on tickets, don’t sweat it! Pull up a bar seat at one of the many sports bars throughout the city – Bleacher Bar, Cask ‘n Flagon, Stats Bar & Grille, The Greatest Bar, Banners Kitchen and Tap or The Sporting Club will all provide a taste of the local sports dedication on game day.
6. Indulge in New England’s culinary traditions
Positioned at the heart of New England, Boston has premier access to some of the best seafood in the nation. Whether you’re at a casual waterside venue like James Hook & Co. or The Barking Crab, or settling into a settee at a more formal restaurant like Row 34 or B&G Oysters, pescatarians will be in heaven with the range of options and freshness. The most popular orders include oysters on the half shell, New England clam chowder, lobster rolls (both buttered and with mayonnaise) and steamed clams.
7. But also seek out regional rising stars of global cuisine
Though seafood is traditional in Boston, we’d be remiss not to mention some exciting spots for global eats. Xenia Greek Hospitality has Krasi and Bar Vlaha, while Yunnan Kitchen serves delicious Dian cuisine from southwest China. For Mexican eats, Borrachito Taqueria bring tacos to Boston via the original NYC outpost.
Boston’s Newbury Street is the perfect place for shoppers © Marcio Jose Bastos Silva / Shutterstock
8. Shop and gallery hop along Newbury Street
Multi-level brownstones line Newbury Street, Boston’s charming one-mile stretch of boutique shops, art galleries, established restaurants and cozy cafes. Of Newbury’s eight blocks, the first (between Arlington and Berkeley) is unofficially dedicated to high-end fashion, with designers like Tiffany’s, Chanel, Loro Piana and Cartier. The sidewalks swell on the weekends, especially in summer – on summer Sundays, the street is closed to vehicular traffic for a pedestrianized-only experience. In winter, storefronts sparkle with holiday displays and in spring, restaurants open their patios, which overflow with patrons sipping spritzers through summer and well into autumn, of which the season is extended by standing heaters and warm drinks.
Local tip: Some of the best shops and bars are not at street level, so look up to find places like Bar a vin 1855, a wine bar above popular French restaurant La Voile, and also down to restaurants like Puro Ceviche Bar.
9. Walk or cycle along the Esplanade
This three-mile path of green along the Charles River stretches from the Museum of Science to the Boston University Bridge. It’s a popular exercise route for locals but also a leisurely way for visitors to enjoy Boston’s natural beauty. Rent a bike and cycle your way along or opt for a stroll.
Join a cruise or sail yourself on the Charles River, an essential Boston experience © Marcio Jose Bastos Silva / Shutterstock
10. Get out on the water
Whether you’re interested in a sailing lesson on the Charles River or entrusting a local captain to do the work on a boat trip in the Harbor, there are plenty of opportunities to experience Boston by water. In addition to sailing lessons, there are outfitters along the Charles for kayaking, canoeing, rowing and stand-up paddleboarding. On the harbor, operators offer everything from hour-long tours, boats for day charter and leisurely sunset cruises. There are also Duck Boat Tours that traverse both land and water.
Planning tip: If you’re booking a harbor cruise at sunset, reserve a table at one of the Seaport’s popular restaurants to beat the crowds coming off your boat. Favorites include Woods Hill Pier 4, Nautilus, LoLa 42 and Strega.
11. Tack on a day trip to one of Boston’s coastal escapes
If you’re visiting during the summer and can add on some extra time to your vacation, consider a day trip to one of Boston’s coastal towns. You make a half-day trip to the North Shore to explore the quaint port towns of Gloucester and Newburyport, or venture down to the South Shore to beach towns like Duxbury and Cohasset. For a longer excursion, drive to Cape Cod (“the Cape,” as locals refer to it). Chatham, Dennis and Orleans are all within a two-hour drive and have one-street towns with bakeries and boutiques to spend the morning at before an afternoon lazing on the sands of the many nearby beaches. Further afield is Provincetown, which can be a long drive but there’s also a fast ferry that runs throughout the summer and which can pick you up from Long Wharf in the morning and whisk you to Ptown in 45 minutes for a day of eating and perusing its artsy streets.
Planning tip: If you opt for the mid-Cape on a summer weekend, leave extra time for traffic as back-up times on Friday evenings, Saturday mornings and Sunday afternoons can teeter on doubling your drive time. Opt for a weekday if possible.
