Top Massachusetts Underground Tours

Boston is heaven for seafood lovers, thanks to iconic dishes such as lobster roll and clam chowder. On this walking tour, dive into the city's seafood delights punctuated with peeks at its colonial and revolutionary history—all with a guide for foodie insights and tips. Enjoy lobster roll and chowder, see Freedom Trail sites, roam the harborfront, and finish with a sweet treat in the North End.

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.

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.

Discover the thrilling history of Boston on this immersive walking tour of the Freedom Trail. Hear tales of Redcoats, smugglers, riots, and midnight riders while reliving the American Revolution as you explore all 16 official sites of the trail. Learn about Boston’s leadership in abolition, women’s rights, education, and immigration over its 400-year history. Explore downtown Boston, hearing stories of legendary figures such as Paul Revere, John Hancock, and lesser-known pioneers and patriots.

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.

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.

Boston is famous for its donuts and has numerous artisanal donut stores, some hidden away from its tourist areas. Instead of hunting them down independently, let a guide lead you there and introduce you to some top donut varieties, enabling you to try flavors and gain insight into the local donut scene you might otherwise miss. Between tastings, browse a market, eat a delicious bakery treat and explore historical neighborhoods such as North End before one final, scrumptious donut sampling.

Discover New Hampshire’s most striking natural wonders on a full-day escape from Boston. This curated tour brings you deep into the White Mountains for a choice between two unforgettable experiences: the adventurous Lost River Gorge or the scenic, nationally acclaimed Kancamagus Highway. Continue to the iconic Flume Gorge, where towering granite walls, waterfalls, and lush forest create a one-of-a-kind landscape. With plenty of time to explore, walk, and capture incredible photos, this tour delivers the perfect blend of nature, fresh air, and adventure—all in a single day.

Have some PRE-GAME Fun before the big game at TD Garden. This fun & unique walking tour is part Pizza & Axe Throwing, part History & Photography, and part Beer & Boston Sports! Discover Boston's oldest neighborhood during this exciting (we have the VERY BEST Tour Guides in Boston - check our reviews!) 2+ hour walk. See FOUR Freedom Trail sites, plus enjoy a slice from Boston’s oldest Pizzeria with a brick oven dating back to 1883. Learn about top Boston sports legebds like World Welterweight Champion, Tony DeMarco, and Bobby Orr. Your Tour Guide will also show you historical sites including the Paul Revere House, Old North Church, Bunker Hill Monument, USS Constitution, and Copp's Hill burying ground. Also look for our popular North End Pizza Tour, Historic Pub Lovers Tour and Boston Seafood Lovers Tour.

Discover Boston, Salem, and Cape Ann with maximum flexibility using this self-guided audio tour. Location-based narration shares colorful local history as you explore—it’s all at your own pace, which means you can stop and start the guide as you pause to take photos, eat lunch, or take breaks. Since the self-guided tour uses offline maps, it even works without cell service or WiFi.