Top Boston Underground Tours

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.

Take a deep dive into the history of the American Revolution on this walking tour of Boston. Your historian guide will focus on the years between 1760 and 1775, a tumultuous time with plenty to talk about. Stroll the Freedom Trail and ask your guide questions along the way to learn things most tourists miss.

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.

Discover some of Boston's most notable historic landmarks—and pair your sightseeing with a pizza crawl—on this time-saving, two-in-one walking tour. With just a guide and small group for company, stroll through the city’s oldest neighborhoods, including Little Italy on the North End. Walk along the Freedom Trail to sights including Paul Revere House and the USS Constitution, and head to local pizzerias for three full-size slices along the way.

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.

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.

Combine two attractions Boston has to offer—delicious food and rich history—on this walking tour that starts in the popular North End and continues along the Freedom Trail. Taste fresh bread, pizza, and a classic Italian deli sandwich at local stops in this historic Italian neighborhood. Then, walk the Freedom Trail to learn about the American Revolution, all while enjoying scenic views of Boston Harbor and the Rose Kennedy Greenway. Explore the charming architecture of Beacon Hill and experience the city's blend of old and new.

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.

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.

Explore Boston’s Freedom Trail as you wish with this self-guided audio tour. Download the iPhone or Android GPS app and start along the trail when it suits you. As you wander between the sites, dip in and out of their backstories, deep-dive into topics that grab your interest, and stop and resume the audio when you wish. The benefit? You’ll enjoy more flexibility than on a fixed-itinerary tour and have more information at your fingertips than if exploring alone.

Escape Boston for a full day in New Hampshire's White Mountains. During the summer route, explore the caves, waterfalls, bridges, and forest paths of Lost River Gorge; during the fall foliage period, travel the scenic Kancamagus Highway instead. Both routes continue to Flume Gorge for a walk through its dramatic granite walls and woodland scenery.

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.

Sample some of the tastiest bites that Boston’s North End has to offer—and enjoy a first-hand introduction to the area’s Italian heritage. Choose between our 3-hour or dynamic 2-hour express tour, and bring your appetite: Follow your guide to top-rated local businesses, and try everything from clam chowder and lobster rolls to cannoli. At the end, enjoy a secret dish revealed only on the day of the tour.

Cover the highlights of the Freedom Trail on this walking tour of Downtown Boston. A shorter route leading between Boston Common and Faneuil Hall Marketplace is ideal for travelers who don’t have the time or inclination to cover the full extended route. A costumed guide adds a theatrical touch to the experience.

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.

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).

Explore Boston’s Freedom Trail independently and on your own time with this audio walking tour. The tour never expires, so take your time to learn about Boston’s history and explore its center in the company of the audio guide. An easy-to-navigate app with GPS allows you to wander confidently throughout Boston.

Discover Boston’s rich past and vibrant present on this small-group (or private) walking tour—a relaxed and informative way to get your bearings if visiting the city for the first time. Gain valuable insight from local guide as you explore spots such as Boston Harbor, Faneuil Hall, Beacon Hill, and the Public Garden. As you wander, learn about the city’s Revolutionary roots, architectural gems, and cultural evolution—and get an understanding of what life is like for modern-day residents.

Travel back in time, to the early years of the United States of America, during this guided walking tour of Boston’s Freedom Trail and beyond. Relive the events of the American Revolution as you pass Faneuil Hall, see the Old and New State Houses, and visit the setting of the infamous Boston Massacre. Then head downtown past Boston Common and the modern John Hancock Tower, finishing in Copley Square.