15 fun and unique things you can only do in Boston

The history, the food, the sports, the accents—Boston is one of the oldest, most distinctive, and most dynamic cities in the U.S. There's countless activities to do, so to help you narrow down your itinerary, we've found 15 incredible options for your next trip to Beantown.

The cobblestone streets and old-world charm of Boston’s oldest neighborhood and its Little Italy provide the perfect backdrop for an enclave of Italian restaurants, bakeries, and coffee bars. Grab a slice of Neapolitan pizza from the nearly century-old Regina Pizzeria, take a side in the great “who has the best cannoli” debate between Mike’s Pastry and Modern Pastry Shop, and perk up with an espresso at Caffé Vittoria before following the Freedom Trail, a 2.5-mile trek to 16 historic landmarks, including Paul Revere’s house, the Massachusetts State House, and the site of the Battle of Bunker Hill.

Boston’s historic waterfront is filled with ships to explore. Located at the end of the Freedom Trail, the USS Constitution is one of the U.S. Navy’s original warships and the oldest still afloat. A land-based museum details the three-mast ship’s history, but to truly appreciate its grandeur you should step aboard its wooden hull on a tour led by active U.S. Navy crew. If you’re visiting with kids, be sure to also stop by the Boston Tea Party Ships & Museum for an interactive lesson in Boston’s most famous event aboard a full-scale replica 1770s tea ship.

What better way to enjoy the nation’s oldest public park than with a little outdoor Shakespeare? Every summer the Commonwealth Shakespeare Company mounts a free production of a new play at the Parkman Bandstand. Alternatively, if you’re visiting in any other season, check the calendar to see when indoor performances are taking place. Or, visit the theater district to see touring Broadways shows like Hairspray (October 18-30) or Hamilton at the Boston Opera House (January 17-March 12, 2023).

Sure, you can catch a baseball game in most major cities, but the nation’s favorite pastime is a different experience entirely when you’re part of the rollicking chorus of 37,000 Red Sox fans at 110-year-old Fenway Park, the oldest stadium in the MLB. If you can’t catch a game, you can visit the Green Monster on a tour of Fenway Park—your guide will take you into the ballpark and the Fenway Park Living Museum while sharing insight into the team’s history and the park itself.

When you’re ready for a break from the urban exploration, hop on a ferry at Long Wharf to the Boston Harbor Islands, a national recreation area and state park made up of 12 islands where visitors can hike, camp, kayak, swim, and explore lighthouses just minutes from the city’s waterfront. The most popular stop is George’s Island, home to a Civil War-era fort that housed Confederate prisoners.

For a taste of a bygone era, head to the eminently charming Beacon Hill neighborhood to stroll down red brick sidewalks past picturesque Federal-style row houses, overflowing flower boxes, and gas-fired street lamps. Acorn Street will lend you the perfect photo op, and on Charles Street, you’ll find quaint clothing and home goods boutiques. Beacon Hill borders the Boston Public Garden, a lovely place to stop for a picnic under the famous weeping willows or take a ride on a swan boat.

Take a trip through the life and times of Boston’s favorite son at the John F. Kennedy Presidential Museum & Library, a striking waterfront building packed with riveting exhibits on the space program, the Cuban Missile Crisis, the Kennedy family, and more.

You’ll find riffs on the state’s official dessert all over town, but only the Omni Parker House serves up French chef Augustine François Anezin’s original Boston cream pie, created at the historic hotel in the mid-19th century.

The Mapparium is a brilliantly colorful, three-story stained glass globe located within the Mary Baker Eddy Library. Visitors walk on a glass bridge that cuts through the sphere’s center, gazing up above to see the north pole. The structure aims to show an undistorted model of the size and relation of the earth’s continents. For example, Africa is far larger than it appears on a standard classroom globe or map. Because the Mapparium’s globe was completed in 1935, the political boundaries of nations remain frozen in time—borders and labels of British colonies and the Soviet Union are depicted.

For one of the world’s most unique museum experiences, take a step back in time to the Isabella Stewart Gardner Museum. This museum is the former home of the legendary patron of the arts and socialite from the late 1800s, Isabella Stewart Gardner. It houses works by some of the world’s most well-known artists, including Matisse, Titian, Degas, Boticelli, and John Singer Sargent. In addition to the vast and eclectic collection of European, American, and Asian art, visitors will enjoy the beautiful courtyard decorated with perfectly kept landscaping. The Gardner was also the site of a mysterious 1990 art heist—the largest private property theft in history—in which $500 million worth of art was stolen. Today, empty frames hang in place of the lost paintings.

For more tranquility, and to get active, spend a morning at Blue Hills Reservation, less than 10 miles from downtown and accessible by car or bus. Blue Hills offers 125 miles of hiking trails and covers ground in the towns of Milton, Quincy, Braintree, Canton, Randolph, and Dedham. In the fall, you can see New England’s famous leaves turning. For an impressive skyline view, climb to the top of Great Blue Hill, a moderate hike that takes a little over an hour. If you’re traveling with little ones or are looking for something less strenuous, the state park offers a number of other easy hikes as well.

While a number of Massachusetts cities may come to mind when thinking of seafood, Boston is not to be missed. If you’re looking to treat yourself, look no further than Atlantic Fish Co, a Tripadvisor Travelers’ Choice Award winner. Go here for chilled oysters and a solid martini. Head to Boston Sail Loft Restaurant for a more casual feel; order the clam chowder—it was voted as the best in the city by Boston magazine. And if you’re craving a lobster roll, try Row 34—regulars swear by it.

The Arnold Arboretum is another place of beauty within the city. While America's oldest public arboretum is a popular destination among tourists and locals alike, you won’t feel crowded here. The 265 acres of sprawling trees, trails, shrubs, and vines will provide the breath of fresh air you were looking for.

Boston is a great place to grab a brew—and with so many breweries, you’ll have a number of choices. Head over to Harpoon to indulge in craft beer and experience their festive beer hall. Or head over to Sam Adams to take a tour and learn how they turn hops into your beverage of choice (and to sample some, of course). If you can’t decide on just one brewery, try a guided tour that makes multiple stops.

Right across the Charles River is Cambridge, which has its own distinct personality and is best-known for being home to Harvard. Start your day off at Harvard Square, where you’ll find a funky mix of restaurants, boutiques, and local color. In the center of the square, you can grab a walking tour map, which will lead you to landmarks such as Mount Auburn Cemetery, Tory Row, and the Longfellow National Historic Site. But before leaving the square, turn a corner down Modica Way to soak in a 16-foot-high, 120-foot-long covered alleyway where street artists paint their best work legally. The constantly evolving canvas has been called one of the Boston area’s most Instagrammable spots. Lastly, feel like an Ivy Leaguer and take a stroll around the historic Harvard campus with the guidance of a student-led tour.