Top Boston Walking Tours

While Boston is home to lots of different food tours, not many let you eat like a local on a trip around an Italian neighborhood filled with mom-and-pop shops. On this half-day guided culinary tour, enjoy rich coffee, cheesy pizza, loaded Italian subs, and much more as you explore Boston’s North End.

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.

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.

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.

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.

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.

Don’t waste time looking for the ideal place to eat as you walk the cobblestone streets of Boston’s North End. Join other passionate foodies to snack your way through the neighborhood’s hidden gems. Your guide directs you to a hidden Italian bakery, an authentic Italian salumeria, and a family-run pastry shop. Visit the Old North Church (or equivalent alternative) and enjoy a rich cappuccino or bold espresso with a pastry.

Many tours allow you to discover the Boston Freedom Trail, but few allow you to do so while accompanied by a guide in revolutionary dress. On this walking tour, learn about the foundation of the US, visiting historic locations such as the Massachusetts State House, Boston Common, the Boston Massacre Site, and much more.

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.

Cover the most important parts of Boston's Freedom Trail on this walking tour. Begin at Boston Common and follow your guide on a journey focused on early American history and the Revolutionary War. As you walk, stop at the top 11 sights, where you can skip the line, saving valuable vacation time.

It can be tough for visitors to know the best venues to experience Boston’s rich Italian culinary culture. On this guided food tour, head to the North End of Boston and learn about the region’s Italian immigrant history, which is kept alive today through the eateries serving pizza, pasta, cannoli, espresso, and much more.

When tracing the roots of American independence, the city of Boston is one of the most important epicenters in the country’s history. The Freedom Trail runs through downtown to Charlestown, taking you on a literal walk through the events that inspired and instigated the American Revolution. Join a local guide for a tour of the entire 2.8 mile (4km) trail which includes visits to Bunker Hill and the USS Constitution so you can hear the full historical tale.

Eat your way through Boston’s North End and learn about its history with this small-group tour. Explore the neighborhood’s Italian heritage in the company of a guide and stroll through the area’s scenic streets. Enjoy a local lunch at a North End eatery and hear stories about the neighborhood’s past.

Discover the best of Boston’s hops and history on a small-group pub crawl along the Freedom Trail. Offered at three separate times, you can easily start at a time that fits with your schedule. Purchase drinks as you please as you visit some of the city’s top pubs with your guide while passing iconic historical sites and learning about Boston's colonial and revolutionary past.

Explore Boston’s North End through its food on a guided walking tour that blends local history with tastings at long-established eateries. This experience offers insight into the neighborhood’s Italian-American roots while helping you navigate its most respected food spots without guesswork. With curated stops and storytelling throughout, it’s an efficient way to understand the area’s culture, avoid tourist traps, and sample classic flavors in a short time.

Boston has such a rich history that it can be tough to take it in by yourself. On this guided walking tour, learn the city’s story, from the Freedom Trail to tales of superstitious Puritans and the US Revolution. Includes the chance to hear about the influential heroes and villains that have called the city home.

Explore Boston’s top 3 attractions on a small-group walking tour in just two hours. A longtime local guide shares insightful historical commentary and fun photo tips to help you capture memorable photos of your adventure. Discover the history behind Back Bay's the iconic architectural landmarks in Copley Square. We’ll take a scenic stroll in the Boston Public Garden to see the colorful flowerbeds and the famous Swan Boats. And for the grand finale in Beacon Hill, find out why Acorn St. is 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.

Discover a whole new side of baseball history with the help of a guide on this tour of Fenway Park, one of baseball’s most beloved stadiums. Revisit the careers of Red Sox greats like Ted Williams, Babe Ruth, and Carl Yastrzemski, celebrate the club’s numerous World Series titles, and tour famous stadium locales like the ‘Green Monster,’ ‘Pesky’s Pole,’ and the Fenway Park Living Museum. It’s ideal for baseball fans, be they locals or tourists.

Go behind the scenes of Boston’s iconic seafood scene with a local guide on a tour that helps you explore the city like a local. Explore the oldest working fish pier in the US, visit family-run seafood shacks, and enjoy tastings of lobster rolls and clam chowder. Plus, learn about sustainable practices and Boston Harbor’s remarkable transformation.

Discover Boston’s North End—one of the city's most historic neighborhoods, and now home to its Little Italy—on a photography walking tour designed for small groups. Immerse yourself in the vibrant atmosphere, and visit many iconic Freedom Trail sights in one trip, including Paul Revere’s House, the Old North Church, and hidden gems off the beaten path. Bring your camera for expert photography tips, perfect for all skill levels.

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.

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.

Visit Martha’s Vineyard on a day trip from Boston to experience the island beauty without the hassle of booking ground and ferry transport. From hotel pickup and drop-off to included ferry tickets, snacks, water, and sightseeing maps, this Martha’s Vineyard excursion is designed for maximum time exploring, with the option to upgrade and include a guided tour of the entire island aboard a high-top, small-group van and explore all six towns on the island, indulge in lunch, and spend more time learning about scenic New England.