Things to do in Boston
Freedom Trail Tours19 optionsMuseums9 optionsBoston City Tour10 optionsBoston Food Tour26 optionsBoston Airport Shuttle7 optionsBoston Ghost Tour13 optionsBoston Trolley Tour7 optionsBoat Tour Boston16 optionsBoston Walking Tour79 optionsNorth End Tours43 optionsConcord Tours8 optionsBike Tour Boston5 options
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Tall Ship Sailing Cruise Boston Harbor: Classic Wooden SchoonersA classic tall ship cruise in Boston Harbor aboard the Liberty Star or Fame, two wooden schooners offering 90-minute to two-hour day sails with views of the city skyline and harbor landmarks. No formal tour narration—the captain and crew share stories about local history and landmarks if you ask. You can bring your own snacks or bagged lunch, though coolers and outside beverages are not permitted. Arrive 15–20 minutes before departure.Is it for me?Choose the Pastries & Prosecco sail on Sunday mornings if you want a relaxed brunch experience on the water; pick a standard daysail if you prefer flexibility on timing and want to spend your time on deck without a set menu. Either way, the lack of formal narration means you're not locked into a script—you steer the conversation with the crew toward what interests you.
Boston & Salem: High-Speed Ferry with Skyline ViewsYou board at Boston's waterfront or Salem's dock, spend under an hour on a high-speed catamaran crossing the Massachusetts coast, and arrive refreshed at your destination without navigating traffic or arranging ground transport. The ferry includes restroom access, an onboard galley, and open-air decks for watching the skyline and coastline pass. Round-trip travel requires purchasing two separate one-way tickets.Is it for me?Book this if you're splitting time between Boston and Salem and want to skip the drive—the ferry is the fastest route between the two cities and arrives you refreshed instead of tired from traffic.
Boston Harbor: Sunset Cruise with Cannon Fire & LandmarksYou’ll board in Boston Harbor as evening falls, gliding past landmarks like Castle Island and the North End steeple while your captain shares stories. Watch sunset colors over the skyline and feel that jolt when the USS Constitution fires its cannon—a little piece of history echoing across the water. It’s relaxed, local, and leaves you seeing Boston differently.
Freedom Trail & Beacon Hill Walking Tour Boston: 2 HoursA two-hour guided walking tour of Boston covering the Freedom Trail, Beacon Hill, and Boston Common with a local English-speaking guide. The route includes stops at Faneuil Hall, Old State House, Massachusetts State House, and Boston Public Garden, ending in the city's first public park. Small groups keep the experience personal; children under 6 join free, and the tour runs in any weather.Is it for me?Choose the small group tour if you want to walk at a steady pace with other travelers and hear your guide's stories without arranging anything yourself. Pick the private tour if you'd rather set the rhythm, ask deeper questions, or explore at your own speed with just your group.
Boston: City Landmarks Bike Tour with Fenway & North EndYou’ll pedal through Boston’s North End with its tempting food scents, cruise past Fenway Park and Beacon Hill’s brick lanes, and catch river breezes on the Esplanade. With a local guide leading the way and plenty of stories en route, you’ll feel both Boston’s energy and quieter corners — plus there’s always talk of cannoli at the finish.
Boston Harbor: Day Sail Cruise on Classic Schooner BoatYou’ll feel Boston slip away as soon as the schooner leaves the dock — city sounds fade and it’s just wind, water, and stories from your local crew. Sail past Castle Island and Long Island Light, watch city landmarks drift by, bring your own picnic if you want. It’s simple but honest: sometimes there’s nothing better than seeing Boston from its harbor.
North End Boston Food Tour: Pizza, Pasta, PastriesThe North End Boston Food Tour is a guided walk through Boston's Little Italy led by a lifelong neighborhood resident, with six to eight tastings including pizza, pasta, an Italian sandwich, cannoli, sfogliatelle, espresso and a complimentary glass of wine and limoncello. The guide shares personal stories of growing up Italian in Boston and takes you to both historic institutions and under-the-radar spots locals know. The tour runs two to three hours and suits all fitness levels; let the guide know about food allergies when you book.Is it for me?Book this tour if you want to eat real food at real neighborhood spots instead of a restaurant built for tourists, and if hearing why each place matters—from someone who grew up eating there—changes how the meal tastes. The guide's personal connection to the North End is what sets this apart from a walking map with stops.
Boston Seafood Tour: Fish Pier tastings with local guideA small-group or private walking tour of Boston's Seaport District that includes behind-the-scenes access to the historic Fish Pier, tastings of local seafood (lobster roll, clam chowder, oysters, tuna hand rolls, and more), and a guide who shares the stories of Boston's fishing industry and maritime heritage. The tour covers roughly 2 miles at a relaxed pace with plenty of stops, and the tastings together equal a full meal.Is it for me?Book the small-group option to join other food travelers and hear stories from a local guide at their favorite eateries; choose the private tour if your group wants the same behind-the-scenes access and tastings without sharing the experience with others.
Boston North End Food Tour: Italian Regional Tastings & WineA three-hour food and wine walking tour of Boston's North End led by the owner, covering five stops that move from Sicily's arancini through Naples, the Amalfi coast and Emilia Romagna without leaving the neighborhood. You taste regional Italian foods tied to the local culture, visit an authentic market and a 160-year-old bakery, learn wine pairing from a certified Italian wine specialist at the oldest liquor store in Boston, and end at a local caffe for espresso, cannoli and gelato. The tour walks only three blocks but covers the whole story of how the North End became Italian.Is it for me?The owner leads every departure, which is why the tour holds together as a story instead of a checklist of stops—you learn how the North End became Italian while tasting the foods that made it happen, not just sampling them in sequence. Book this if you want a guide who knows the neighborhood's small businesses by name and can explain why each one matters to the community's history.
Sunset Sailing Cruise Boston Harbor: Classic Tall ShipA 2-hour sunset sailing cruise on Boston Harbor aboard a traditional tall ship, departing from Fan Pier Marina with sails raised and no formal narration — just the crew, the water, and the city glowing in twilight. Drinks are available for purchase onboard, including beers brewed locally and cocktails made with Boston-distilled spirits; bring your own snacks or bag lunch if you like. Arrive 15–20 minutes early to check in, and note that children must be accompanied by an adult.Is it for me?Book this cruise if you want to see Boston from the water at the moment the city lights come on, without a guide talking over the view — the sails go up, the skyline glows, and the rest is yours to take in at your own pace.
Boston: Freedom Trail, Beacon Hill & Back Bay Walking TourYou’ll walk Boston’s Freedom Trail from Faneuil Hall through Beacon Hill’s gas-lit lanes to Back Bay’s grand brownstones—all with a local guide who knows every story behind each brick. Expect laughter at quirky stops like Cheers or the duckling statues, plus quiet moments in leafy gardens. By Copley Square, you’ll feel both Boston’s weight of history and its everyday pulse.
Martha's Vineyard Day Trip from Boston with Ferry & Optional Island TourYou get picked up from your Boston hotel, driven to Woods Hole with live commentary about the region's history, and have thirty minutes to grab breakfast before boarding the 9:30am ferry. Once on Martha's Vineyard, you have six hours free to explore, with the option to join a three-hour guided van tour through all six towns. Round-trip ferry tickets, snacks, water, maps and a discount food card are included, and you're back in Boston by 6:30pm.Is it for me?A good fit if you want a full day on Martha's Vineyard without arranging your own transportation or ferry tickets from Boston. Plan to be out from early morning until around 6:30pm—that's what gives you the coach ride with commentary, breakfast time in Woods Hole, and six hours on the island all in one day.
Boston to Plymouth Day Trip: Mayflower II, Quincy & Plimoth PatuxetYou’ll travel from Boston through presidential Quincy and along New England’s coastal towns before exploring Plimoth Patuxet Museum and stepping aboard Mayflower II. Expect hands-on history, local stories (and accents), plus lunch by Plymouth Harbor—all with easy pickup and small group comfort.
80-Minute Historic Boston Trolley Tour: Freedom Trail SightseeingAn 80-minute narrated trolley tour of Boston covers 80 historic sites along the Freedom Trail, including the Old State House, USS Constitution, and Paul Revere's House. Departures run every 20 minutes between 9:30 a.m. and 4:30 p.m. from Atlantic Avenue at 255 State Street. The tour is fully narrated in English, family-friendly, and wheelchair accessible.Is it for me?Board at Atlantic Avenue near State Street without a car or hotel pickup—the trolley runs every 20 minutes, so timing your arrival is simpler than coordinating a tour departure, and you stay seated the entire 80 minutes instead of walking the 2.5-mile Freedom Trail on foot.
Lexington & Concord: Revolutionary War Trolley Tour 90 MinYou ride 90 minutes through Lexington and Concord's Revolutionary War sites in a climate-controlled trolley with a guide in authentic period dress. The tour covers the Battle of Lexington Green (April 19, 1775), the second battle location, and Colonial American history. Pickup and drop-off are included; the trolley is wheelchair accessible and suitable for all fitness levels.Is it for me?Book this if you want to see the April 19, 1775 battle sites without driving between them or navigating the route yourself — the trolley and fixed schedule handle both, leaving you free to listen and look.
Boston View Observation Deck: 360° City Views & Rooftop BarYou get timed entry to all three observatory floors, indoor and outdoor decks, access to the rooftop bar and bistro, and interactive exhibits that let you plan the rest of your Boston trip. Pick your entry window when you book, and the ticket is ready when you arrive at Prudential Tower.Is it for me?Book this if you want the clearest view of Boston's layout and landmarks without arranging your own transportation or timing — the timed entry means you skip the line and pick the hour that works for your schedule.
Boston Freedom Trail: 11 Historic Sites & Costumed GuideYou walk 11 of Boston's 16 Freedom Trail landmarks in 90 minutes with a costumed guide trained as both historian and actor. The route covers the Boston Massacre Site, Old State House, Granary Burying Ground, Old South Meeting House, and Faneuil Hall, with no navigation or planning required on your part. All fees are included, and the pace suits families, solo travelers, and anyone comfortable with a gentle, guided stroll through downtown Boston.Is it for me?Book this if you want Boston's Revolutionary history without the work of planning stops, reading maps, or arranging entry fees separately—the fixed route and costumed guide handle all three, leaving you free to listen and walk.
Boston North End: Dessert & Cocktail Walking Tour, Skip LinesYou’ll stroll through Boston’s North End sampling classic cannoli, gelato, and cocktails while skipping those long bakery lines. A local guide shares stories at spots like Paul Revere House and Old North Church. Expect laughter, new flavors, and small surprises along the way — plus a little powdered sugar on your shirt.
Boston to Newport: Breakers & Marble House Day TripYou get picked up at your Boston hotel and driven to Newport for a full day that includes entry to two of the grandest Vanderbilt mansions, a guided city tour hitting the historic sites, and free time to explore on your own. The small-group format keeps it under 20 people, and all transport, mansion admission, and a discount card for the Tennis Hall of Fame are included — you just show up ready to walk.Is it for me?Choose this if you want to see Newport's two most famous mansions without arranging your own transport or buying separate tickets — the fixed schedule and included pickups mean you leave your hotel and show up at The Breakers without any logistics to handle.
Boston Freedom Trail: GPS Walking Tour & USS ConstitutionYou walk the Freedom Trail from Boston Common through downtown, the North End, and across to Charlestown on your own schedule, guided by GPS and professional narration through the WalknTours app. The tour covers 16+ stops including Paul Revere's House, Bunker Hill, and USS Constitution, never expires, and works on two phones from a single purchase.Is it for me?Best for solo travelers and couples who want to explore Boston's Revolutionary history without booking a group or waiting for a guide—the app's GPS navigation and your own pace mean you stop as long as you want at each site and walk the full Freedom Trail in one day or split it across visits.
