Top Boston Private Sightseeing Tours

Discover the best of Boston and see the sights that interest you most on this half-day tour. Board your private vehicle along with your group and explore key landmarks in the comfort of an air-conditioned vehicle. See Harvard University, Fenway Park, the Boston Public Library, Beacon Hill, and much more while listening to commentary from your driver about Boston’s history.

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.

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.

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.

This tour is the perfect way to orientate yourself to Boston, to see not just the historic sites, but the entire city. On this tour we'll take you into all the city neighborhoods and along the sites of the Freedom Trail. We'll share the history and legends of the city, keep it topical with current day fun facts and light hearted stories. All guides are fully licensed and approved Boston tour guides, driving luxury and livery insured vehicles.

Explore the best that Boston has to offer on this hop-on hop-off tour of the city. See Boston’s top attractions—like the USS ‘Constitution’ and the Boston Tea Party Ships and Museum, to name a few—on the loop. Enjoy discounted admission to attractions like the Boston Tea Party Ships and Museum with the purchase of your tour.

See some of the top attractions in Boston from the waterfront on this narrated sightseeing cruise. Explore Boston Harbor and see the city’s historic sites while listening to live commentary on board. Pass landmarks like the Boston Tea Party ships, USS Constitution, and Boston Light—the oldest continuously manned lighthouse in the United States.

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.

Revel in the history of Fenway Park, one of baseball’s most beloved stadiums, during this guided tour. 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.

Discover some of Boston’s deepest, darkest secrets on a “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.

Enjoy some of the best pizza in Boston on this walking food tour. Stroll through the city’s oldest neighborhoods, including, appropriately, Little Italy on the North End. Walk along the Freedom Trail that leads to 16 historically significant sites, like Paul Revere House, Old North Church, and the USS ‘Constitution,’ to name a few. Visit some of Boston's best pizzerias and enjoy a slice at each. It’s a fun and flavorful way to get to know Boston.

Experience the best of New England’s marine wildlife on this guided whale-watching cruise around the Stellwagen Bank National Marine Sanctuary. Hop on a high-speed catamaran that gets to and from the whales in the least amount of time possible. See humpback and fin whales, plus Atlantic white-sided dolphins with the help of a naturalist guide. The on-board galley offers food and beverages for purchase during the trip.

Explore Boston on foot with this small group walking tour. See highlights like Boston Harbor, Custom House Tower, Faneuil Hall, and Quincy Market. Learn the true story behind the Boston Massacre, and if you’re lucky, get a glimpse of government in action at the Massachusetts State House. See Beacon Hill, the Freedom Trail, and the lovely Boston Public Garden. Rest your legs and enjoy time with your local guide.

There’s no need to worry about sore feet, buses, driving or missing views on this small-group Boston tour and cruise. Board an air-conditioned minivan and enjoy the driver-guide’s commentary as you see Harvard University, the USS Constitution and more. Visit the Bunker Hill Monument and Quincy Market and finish with a relaxing harbor cruise to admire Boston’s skyline and Tea Party site. With numbers limited to seven and hotel pickup and drop-off included, the tour can’t help but feel personalized.

Join Boston's only award-winning, original, Martha's Vineyard Day Trip! Leave the trouble of driving to someone else and enjoy a day trip to Martha’s Vineyard from Boston. Then, take a short cruise to Martha's Vineyard then enjoy free time to explore or upgrade to add an island tour. Complimentary snacks, bottled water, island guidebooks and a discount card with island perks are provided during the drive.

Explore Boston by boat with this cruise on the Liberty Clipper. Help the crew hoist the sails or simply find a spot on deck to enjoy the views. Your captain creates a route depending on wind direction, heading toward the outer harbor for a glimpse of Fort Independence, or sailing toward East Boston for views of the Charlestown Navy Yard, home to the USS Constitution.

Discover the stories behind historic Boston sites on a self-guided tour of downtown, and enjoy the flexibility to experience the city on your own schedule. Booking this tour means access to audio guides that never expire, so you can explore as much—or as little—as you want at a time. The included GPS-enabled app gives turn-by-turn directions as expert tour guides narrate revolutionary history and more.

Maximize time in Boston with a private sightseeing tour. Get picked up at your hotel or the address of your choice in Boston and set out on a half-day excursion. Learn about the history behind top landmarks including the Paul Revere House, the USS Constitution, and the Bunker Hill Battle Monument. Explore several neighborhoods including Back Bay, Beacon Hill, and the South End.

Explore the city of Boston in comfort on this private driving tour that covers the main attractions and highlights. Perfect for those who are short on time but want to see the sites, this tour features a stop at the Freedom Trail, which includes Kings Chapel, Old South Meeting House, the Old State House, Paul Revere’s House, and Boston Common. Then, visit Bunker Hill and learn how the battle here impacted the Revolutionary War.

Discover the spooky stories behind Boston’s historic places on a self-guided walking tour that lets you explore at your own pace. Turn-by-turn directions lead you through the streets of Boston, from the Boston Athenaeum to the Central Burying Ground, while a narrator shares theatrical tales from the city’s past. Choosing a self-guided tour means experiencing the city on your own terms, with more flexibility than a group excursion offers.

Discover Boston’s famed Freedom Trail on a private walking tour through the city. Follow your dedicated guide past key landmarks including Paul Revere’s house, Old North Church, Boston Common, Faneuil Hall, and much more, customizing the tour to your group’s interests. While you walk, your guide regales you with information about Boston’s history with particular emphasis on the American Revolution and independence.

Boston is steeped in history yet still exudes style that lends the city a contemporary feel. Discover the centuries-old landmarks set amongst the skyscrapers during this private, small-group guided tour. All admission tickets are included for attractions like the Bunker Hill Monument and USS Constitution. Join your guide for a narrated drive around the Freedom Trail followed by a narrated historical Boston boat ride. When you visit Harvard, be sure to rub the bronze statue’s foot for good luck!

Taste your way through Boston with a private food-focused tour. Meet your guide for a half-day city stroll that includes popular landmarks such as Boston Common, the Paul Revere House, and the Bunker Hill Monument. Sample several traditional flavors of Boston including Boston clam chowder and Boston cream pie. Learn about local history and culture from your private guide.

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