Top Boston Cultural Tours

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.

Traverse Boston and learn all about the city’s history while you sightsee on this group walking tour led by a father and son duo. See the Old North Church, the Paul Revere House, Old City Hall, and more, without worrying about getting lost or missing out on hearing the stories behind the sights. An expert guide leads the tour to bring Boston's history to life.

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.

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.

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.

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.

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.

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.

Learn more about the history of Lexington and Concord from the comfort of an air-conditioned trolley. Sit back, relax, and listen to the live commentary from your guide dressed in period costume as you pass Lexington and Concord’s heritage sites. This isn’t a hop-on, hop-off bus so you can remain on the trolley for the full 90 minutes. Gratuities are not included.

Eat your way through Boston’s North End and learn about its history with this 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 featuring arancini, pizza, Italian meats and cheeses, a pasta course, cannoli, and more, and hear stories about the neighborhood’s past.

Experience the Black Heritage Trail and get to know more about Civil War-era Boston on this small-group walking tour. In the company of a guide, head out into Beacon Hill and hear stories about the Underground Railroad, Boston Brahmins, and other historical facts. Enjoy a focus particularly on the Civil War years.

Get the true Boston experience with your 2-hour Segway tour! Starting with the same route as your 1-hour tour before gliding your way through the Longfellow Bridge and into Cambridge where the magnificent Boston skyline can be seen in all its beauty. From the sparkling river to the tall buildings stretching into the sky, the view is breathtaking and a memory that will last a lifetime! You will then loop back through Beacon Hill and back through Downtown Boston. Sites of the Freedom Trail that you see in the 2-hour tour include all of those in the 1-hour in addition to the Boston Common, King's Chapel, Boston Latin & Benjamin Franklin Statue, Old South Meeting House, New State House, and the Corner Bookstore. You will also get to see the most photographed street in America - Acorn Street and so much more! The 2-hour tour is truly a very comprehensive and exciting tour of the city and it's most important landmarks from both past and present.

Learn about the Boston Tea Party and Boston’s revolutionary history at your own pace with this private self-guided audio walking tour. Download the app to your phone and use it whenever you like, even offline. Follow the route and hear stories about Boston’s history and the sites along the way.

Walk in the footsteps of America’s revolutionaries with our immersive Boston Freedom Trail audio tour! Unlike crowded tours, this guide brings history to life at your pace, letting you explore iconic sites like Paul Revere’s House, the Old North Church, and Boston Common while uncovering hidden stories and bold personalities that shaped the nation. Hear expert insights, stop and start anytime, and skip the pricey tour guides—just download, plug in, and let history unfold in your ears. Join thousands of travelers who’ve rediscovered Boston’s past like never before—start your journey today! *Download the Shaka Guide app to access the purchased tours*

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.

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.

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.

Discover a history of resistance among Beacon Hill’s cobblestone streets with a self-guided smartphone tour of underground railroad sites. Vivid audio narration brings to life the stories behind landmarks from the Charles Street Meeting House to Boston’s first integrated school. You won’t be limited by a guided tour’s fixed schedule, so you can pause for photos, take breaks, and enjoy the experience at your own pace.

Relive one of the most important events leading up to the American Revolution and learn about a side of the story most tourists miss on this guided tour of the Boston Tea Party Ships and Museum. Explore authentically restored tea ships with the help of a guide as you get their insights into this pivotal event, and throw some of your own tea into Boston Harbor. It's an ideal experience for American history buffs, tourists, and locals alike.

Immerse yourself in the ghostly mysteries of Boston’s historic streets. History, heroism, and horror surround you on this walking tour of Boston’s strangest sites. You will see Boston Common through a new lens and explore the sites of pivotal moments in America’s birth while listening to tales of death both heroic and senseless.

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.

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.

Enjoy a more personalized way to explore Boston’s Beacon Hill—and benefit from plenty of in-depth commentary along the way—on this small-group walking tour of the popular neighborhood. Be sure to bring your smartphone or camera along: Your guide leads you straight to many of the neighborhood's most photogenic sights, including Acorn Street: the most photographed street in Boston.