Top Massachusetts Sightseeing Tours in 2026

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.

Walk the quads of the campus that inspired astronauts, Nobel Peace Prize winners, and famed innovators in just about every discipline on a student-led tour of the Massachusetts Institute of Technology (MIT). Get an inside look on what it’s like to attend the prestigious university and hear real stories about what makes MIT special.

If you have limited time but still want to see all that Martha’s Vineyard has to offer, then book this private sightseeing tour. You’ll pass through the island towns and scenic landmarks with a local guide, who will tell you all about the area, and allow time for plenty of photo stops. You’ll also be driven from place to place in a comfortable, luxury minivan.

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.

Walk Salem’s dark past under moonlit streets and learn true stories of witch trials, haunted houses, and restless spirits. A clear, friendly voice leads you through historic places and shares tales that send chills. You start when you want. Pause to read old inscriptions, stand before haunted buildings, or peer down alleys where shadows linger. Visit The Witch House, the Old Burying Point Cemetery, The Custom House, and hidden corners locals whisper about. The guide also shows you secret paths others rarely walk. The tour works without internet. It gives you walking directions, spooky facts, and tips you’ll use again. The audio stays on your phone forever. Download the tour, put on your shoes, and explore Salem’s haunted history—step by step, story by story, at your own pace.

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.

Explore Boston at your own pace with this hop-on hop-off trolley tour. Visit landmarks like Faneuil Hall, the Boston Tea Party Ships and Museum, and the Prudential Center, while enjoying insights from engaging guides. With flexible routes, discounted attraction admissions, and trolleys departing regularly, this tour is the perfect way to experience Boston’s history and charm.

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.

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.

Delve into Salem’s past beyond the notorious witch trials on a walking tour that ties four centuries of history into the context of this modern Massachusetts town. Stop at important landmarks in the historic center and learn about Salem's seaport origins, early colonial culture, and illustrious former residents from a guide who knows all the details.

The Salem Witch Trials was a period in history that is easily misunderstood. On this walking tour of Salem, follow your guide to main sites such as the witchcraft memorial and courthouse, as you listen to true tales of paranormal activity, centuries-old murder & astounding history. Plus, this Salem walking tour starts in the late afternoon leaving you plenty of time to fill up the rest of your day with activities.

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.

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.

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.

Travel back in time to colonial New England on a historic walking tour. Your costumed and in-character guide gives you an immersive understanding of life during America’s infancy. Hear exclusive stories about the country’s Founding Fathers and discover iconic historical sites on this tour that covers approximately 1.2 miles (two kilometers).

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.

When night falls across Salem, it's the perfect time to explore the city’s spooky and sinister past on a haunted history tour. On this top-rated walk through one of America's most haunted places, follow a guide who is deep-rooted in the town's history and paranormal activities. Walk along lamplit streets while listening to legends and true tales of witchcraft, murder, mayhem, and more. Visit sites related to the infamous 17th-century Salem Witch Trials, and hear about the ghostly spirits said to still rattle through the town’s historic homes and graveyards.

Explore Boston’s must-see attractions in one tour. Walk along the picturesque streets of Beacon Hill, home to Acorn Street, the most photographed street in Boston. Discover the most scenic locations in the Boston Public Garden and Back Bay’s beautiful 19th-century residential neighborhood.

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.

See some of the top attractions in Boston from the waterfront on this narrated sightseeing cruise. Explore the world-famous Boston Harbor and see the city’s historic sites while listening to live commentary on board, from tales of the Revolutionary War to local legends. While you cruise, enjoy views of the city skyline as well as the Boston Harbor Islands, USS Constitution (“Old Ironsides”), and the Bunker Hill Monument.

Discover some of Boston’s deepest, darkest secrets that lots of tourists miss out on by joining this “frightseeing” tour aboard the Trolley of the Doomed, which roams around the haunted streets and burial grounds of Boston. Your costumed host provides illuminating insights into the history of the city's spookiest sights, such as Copp’s Hill Burying Ground.

The tryals have left a footprint on Salem, and the world, that still echo 334 years later. Join us on our 90min walking tour as we visit historic locations and lay the groundwork to explore and unpack what happened in Salem in 1692. Shedding light on how a community driven by fear and led by religious ideology and zealotus extremism, executed 20 innocent people. We invite you to be part of our story and Uncover the true history of Salem. -All tour guides are licensed by the City of Salem and are professional storytellers .

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.