Top Massachusetts Sightseeing Tours

Explore the best of Boston at your own pace on a hop-on hop-off trolley tour of the city. Choose from a 1- or 2-day pass and see Boston’s top attractions, including the USS Constitution, the original bar from TV show “Cheers,” and the Faneuil Hall Marketplace, to name a few. The pass includes discounted admission to the Boston Tea Party Ships and Museum, to enjoy during or after the tour.

See the landmarks and highlights of Boston from the water on this sightseeing cruise in Boston Harbor aboard a 1920s-style yacht. Snap photos and enjoy a unique perspective of the harbor, very different than a typical walking or driving tour through Boston. Highlights include the USS Constitution, Bunker Hill Monument, Old North Church, and the USS Cassin Young.

Learn about Salem’s mysterious past on this guided walking tour of the city. Follow your historian guide through Salem, listening to 400 years of history, and admire the old architecture that dates back to the early colonial period. Find out the truth about the 1692 Salem Witch Trial hysteria, which has influenced literature and pop culture. For a spookier experience, select the nighttime tour led by lantern light.

Learn about the Battle of Lexington and Concord at your own pace with this self-guided audio driving tour. Download the app and choose to start the tour whenever you are ready. Drive the route of the first battle and listen to the stories that queue up to play with your GPS.

Learn about Boston’s revolutionary history on a walking tour that emphasizes good storytelling. Enjoy personalized attention from your guide in your small group as you walk a curated route that includes the Freedom Trail. Visit well-known sites as well as more local places and develop an understanding of modern Boston along with its history.

Learn all about Salem's dark history and the witch trials at your own pace with this private, self-guided audio tour. Start and complete the tour whenever it suits you, enjoying offline capability and stories that play automatically via your phone’s GPS. Includes a full itinerary, tips, photos, and videos. Lifetime access lets you use the tour anytime, on any trip.

For anyone thinking of attending Harvard, or for those who simply want a glimpse of college life at the famous university, this tour is a must. Get an exclusive account from current Harvard students, who provide key insights into the life and times at Cambridge with a theatrical, humorous flair. Check out the old buildings at Harvard Yard and Harvard Square and learn about the school’s storied past. Illustrated map of Harvard Square included. Choose from several departure times throughout the day.

Experience Boston and Cambridge on a narrated morning or afternoon cruise. After boarding at Lechmere Canal Park, embark on a journey down the Charles River and check out Beacon Hill, Esplanade Park, the Back Bay, Boston University, Fenway Park, M.I.T., Harvard, and other important landmarks. Hear entertaining stories about the region from your captain and crew and enjoy a snack or drink on board.

Get the best chance of seeing whales off the coast of Gloucester, Massachusetts, by booking this half-day whale-watch cruise. Your experienced captain and crew know the whales’ feeding and swimming patterns and keep close tabs on where they’re hanging out. Spread out on the deck of the boat and enjoy being out in the open air while you find whales, then get ready to snap photos of breaching, spouts, and tail slaps.

Discover two of the USA's–and the world’s–most prestigious and historic colleges with exclusive access and a guided tour of each. Explore iconic campus buildings and statues, learn about whimsical traditions passed down through generations of students, visit key historic moments in both colleges’ histories, and hear about some of their most famous alumni.

End a day in Boston the right way with a sunset sightseeing cruise on Boston Harbor. See all of the harbor’s historic attractions as well as the city’s modern skyline, and witness the USS Constitution’s traditional sunset ritual: a ceremonial firing of the cannon of the oldest commissioned sailing ship in the US, and a lowering of her flag, signaling the end of the day.

Explore the best of Boston on this hop-on hop-off trolley tour. Board at one of the stops, then hop off wherever you like, explore independently, and get back onto the trolley when you’re ready. Alternatively, ride the 2-hour loop in one go, listening to the informative commentary. Tickets are valid for one or two days, and while admission tickets aren’t included, enjoy discounts to some top Boston attractions.

RideAway Adventures has been awarded the best tours on Cape Cod 12 years in a row. We have the only fully ACA certified guide staff on Cape Cod. Our tours stay at low numbers so that it is a fun and unique experience for every participant. Our equipment is always top of the line and this area is perfect for all levels of kayakers.

Explore Boston on a trolley tour that’s timed to catch sunset over the Charles River. Many Boston sites are illuminated—and uncrowded—at night, making this an ideal time to explore Boston Harbor, Cambridge, the Public Garden, and more. Live narration from an experienced guide showcases the stories and culture behind each place you visit, from stylish seaside neighborhoods to revolutionary war–era landmarks.

Explore Boston’s top 3 attractions on a small-group walking tour in just two hours. A longtime local guide shares insightful historical commentary of the famous sites along the way as well as fun photo tips to help you capture memorable photos of your tour experience. Discover the history behind Back Bay’s diverse architectural landmarks in Copley Square. Enjoy a scenic stroll through the Boston Public Garden to see colorful flowerbeds and the famous Swan Boats. For the grand finale, we'll visit Beacon Hill’s Acorn Street, known as known the most photographed street in Boston. Designed for history buffs, urban explorers, smartphone users, and casual photographers, this guided walking tour blends engaging historical commentary with photo tips. It is not a technical photography class.

Experience Boston like never before with Boston Sightseeing, where our double-decker open-top buses offer unparalleled views above the bustling streets. We're dedicated to delivering top-tier tour services, ensuring you see the city in style and comfort. Explore Boston at your own pace with our flexible hop-on, hop-off tour, featuring eight strategic stops along the route. Perfect for first-time visitors, it's a fantastic way to get acquainted with the city's layout and landmarks. Immerse yourself in live commentary from our knowledgeable guides, who share insider insights into Boston's rich history and vibrant culture. Known as the Cradle of Liberty, Boston is steeped in revolutionary stories and modern-day marvels. Don't miss out on the best of Boston, Join us and discover the city's charm and allure with Boston Sightseeing.

Taste your way through the heart of Cape Cod on a relaxed, flavor-packed food tour through Chatham’s most iconic streets and hidden gems. Led by a local expert, this 3-hour walking tour features multiple tasting stops with hand-picked seasonal bites from beloved local spots. It’s a delicious way to explore the area, whether it’s your first visit or your summer tradition. Along the way, hear the stories behind the food—tales of tradition, local legends, and the people who make Chatham so special.

Walk the Freedom Trail with a guide in historic costume on a tour from Boston Common to Faneuil Hall, a 1.2-mile route that covers important sites in the heart of Boston. This tour's shorter distance lets you follow in the footsteps of the founding fathers and American revolutionaries without making the more strenuous trek all the way across the Charles River, finishing in a spot that’s convenient to top Boston attractions.

Hop into a duck boat—s renovated World War II amphibious vehicle—for a comprehensive city sightseeing tour of Boston. Pass Boston Common, Quincy Market, the Celtics' home turf at TD Garden, and much more. Then splashdown into the Charles River for a view of the city by boat. Learn all about Boston's history and landmarks as you go.

If you want to explore Salem's haunted history without getting lost in the crowd, go at your own pace with an affordable, self-guided smartphone tour. Simply download the touring app to your phone, and start and stop the tour on your own schedule as the pre-recorded narrator shares the history of haunted locales like the Ropes Mansion, Salem Witch House, and Old Burying Point Cemetery, where many witch trial victims were laid to rest.

See more of Martha’s Vineyard without planning routes or navigating on your own on this all-island bus tour. Multiple scheduled stops let you step off to explore, take photos, and browse key areas, while onboard screens provide historical context for what you’re seeing. With guided narration and built-in free time, the tour balances orientation, learning, and independent exploration in one efficient experience.

Journey into early American history at the Plimoth Patuxet Museums, located near Boston in Plymouth, Massachusetts. Three outdoor exhibits reveal what daily life was like in the New England of the 1600s: Plimoth Patuxet, Mayflower II, and Plimoth Grist Mill. You can opt to visit one, two, or all three to learn about the Pilgrims and Native American Wampanoag in the colonial era.

Enrich your New England road trip with a private self-guided audio tour of Cape Ann that you can listen to as you drive. Filled with evocative tales and historic information, the tour leads you on a scenic loop between Gloucester and Rockport, highlighting the region’s top landmarks and attractions. The convenient app-based guide allows you to travel at your own pace and stop whenever you wish.