Top Massachusetts Private Sightseeing Tours

Taste your way through the vibrant streets of Provincetown on a relaxed, flavor-packed walking food tour blending local bites with rich cultural history. Led by a local guide, this 3-hour experience explores one of New England’s most unique seaside towns, with multiple tasting stops at locally loved eateries and hidden gems. Provincetown is unlike anywhere else on Cape Cod—known for its thriving arts scene, maritime roots, and its role as one of the most welcoming LGBTQ+ destinations in the country. As you explore iconic spots like Commercial Street, you’ll enjoy curated tastings while hearing the stories that make this town unforgettable. From waterfront views to lively streets filled with character, this tour offers the perfect mix of food, history, and local insight—whether it’s your first visit or a return to a favorite escape.

Learn about the Battle of Lexington and Concord at your own pace with this self-guided audio driving tour. Download the app and choose to start the tour whenever you are ready. Drive the route of the first battle and listen to the stories that queue up to play with your GPS.

This half day private car tour is a perfect way to visit the Revolutionary War towns of Lexington and Concord and see the site where the "shot heard round the world" was fired. We'll take the same route as Paul Revere, stopping at the most significant sites along the way to give a detailed account of what and how things unfolded in April 1775. The travel time from Boston to these towns is 45 minutes each way and you'll be in one of our comfortable private vehicles with an experienced, knowledgeable and licensed tour guide.

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.

Are you looking for a way to see all 16 Freedom Trail sites without joining a tour group? Explore at your own pace with this self-guided walking tour. • Find out about Samuel Adams, the one man on whom you could maybe blame the entire American Revolution and other key Freedom Trail players • Hear from producer Daniel Berger-Jones, a local educator and tour guide • Do it all in 120 minutes or linger at stops along the way with complete control over when you start and finish • Get unlimited use before your booking date and after it • Use the virtual tour option at home Once you’ve booked, you’ll receive a ticket with instructions and a unique code listed under “Before You Go”. Then simply install the Voice Map app and enter your code. The app displays directions to the starting point, and when you’re in the right place, pop in your headphones, and just tap start. Voice Map has automatic GPS playback, with turn-by-turn directions. It also works offline.

Learn all about Salem's dark history and the witch trials at your own pace with this private, self-guided audio tour. Start and complete the tour whenever it suits you, enjoying offline capability and stories that play automatically via your phone’s GPS. Includes a full itinerary, tips, photos, and videos. Lifetime access lets you use the tour anytime, on any trip.

Explore Boston’s history, culture, and culinary heritage on this private tour. Delve into the city’s pivotal role in America’s founding, stroll historic neighborhoods, and hear stories that tie past and present together. The private format ensures your day is paced to your interests while minimizing logistical hassles, giving you a meaningful and personalized overview of Boston.

If you have limited time but still want to see all that Martha’s Vineyard has to offer, then book this private sightseeing tour. You’ll pass through the island towns and scenic landmarks with a local guide, who will tell you all about the area, and allow time for plenty of photo stops. You’ll also be driven from place to place in a comfortable, luxury minivan.

Taste your way through the heart of Cape Cod on a relaxed, flavor-packed food tour through Chatham’s most iconic streets and hidden gems. Led by a local expert, this 3-hour walking tour features multiple tasting stops with hand-picked seasonal bites from beloved local spots. It’s a delicious way to explore the area, whether it’s your first visit or your summer tradition. Along the way, hear the stories behind the food—tales of tradition, local legends, and the people who make Chatham so special.

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.

Experience the best of Cape Cod in your own time without overlooking any sights with this self-guided driving tour. Download the app with its GPS map, audios, and text, and hit the road from the Cape Cod Visitor Center. Follow the route to see and learn about the peninsula's lighthouses, beaches, and sights, and take optional detours to relax, hike, or delve deeper into the cape's history. For lifetime access, you can dip in and out whenever you wish.

Unearth the charm of Oak Bluffs on this self-guided walking tour, where the rich history and vibrant culture of this New England seaside town come alive. Wander among whimsical gingerbread cottages, enjoy stunning harbor views, and learn how this area evolved from a Methodist camp meeting site to a celebrated resort. This tour highlights the unique blend of architecture, community spirit, and African American heritage that defines Oak Bluffs, making it a delightful exploration of summer memories and local stories. — Discover the distinctive Victorian architecture and intricate cottages — Explore the historical significance of Oak Bluffs as a cultural hub — Enjoy scenic ocean views and shaded park paths during your stroll — Perfect for history buffs and those seeking a unique coastal experience

See all of Boston and Cambridge from the comfort of a heated and air-conditioned modern minivan. This is a half-day driving tour that takes you through every highlight of Boston and Cambridge. The drive will include sights such as the Old North Church, Paul Revere's house, Faneuil Hall, Boston Common, Beacon Hill, Bunker Hill Monument, USS Constitution, Harvard, MIT, Copley Square, Boston Public Library and so much more! The tour is mainly driving, however we will (optionally) stop a few times to briefly (5-10 minutes) get out of the car for photo opportunities and a closer look at some sights! Listen to stories about Boston's past, learning about the American Revolution and the city's duality of religious morals and corruption.

Cover some of Boston’s top historical sights on this guided Freedom Trail walking tour. Discover 11 locations in the attraction-packed Boston Common, including the graves of Paul Revere and Samuel Adams. Listen to entertaining, informative stories along the way, as you cover the history of the infamous Boston Tea Party and Boston Massacre.

Uncover Nantucket's rich history and charm on this self-guided audio tour. Using our app, you can explore at your own pace as you stroll down cobblestone-lined Main Street and learn about how Nantucket evolved from the worlds whaling capital to the tourist destination it is today. Admire meticulously preserved 18th-century homes, each whispering tales of the island's whaling past. Explore iconic landmarks like the Atheneum, the Hadwen House, and Straight Wharf, a bustling hub since the 17th century. All along the way, captivating stories, insights, and local recommendations bring Nantucket's vibrant heritage to life.

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.

The tour will take you from the decks of the Mayflower Two, a faithful replica of the Pilgrims’ ship, and end at the historic Jabez Howland House, the last standing home in Plymouth where Pilgrims actually lived. Along the way you'll walk for an hour and about a mile as you explore Plymouth rock, statues, houses, gardens, churches and sites linked to the Pilgrims. Go at your own pace, anytime. This is the best deal in town, don't miss out on the sites while in town.

Upgrade your drive through scenic Cape Cod with this private self-guided tour you can download onto your phone. The audio narration plays based on your location, letting you start, stop, and skip stops whenever you like. You control your time and pace, enjoying a personalized experience without the constraints of traditional tours.

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.

Enrich your New England road trip with a private self-guided audio tour of Cape Ann that you can listen to as you drive. Filled with evocative tales and historic information, the tour leads you on a scenic loop between Gloucester and Rockport, highlighting the region’s top landmarks and attractions. The convenient app-based guide allows you to travel at your own pace and stop whenever you wish.

History enthusiasts will love this private tour of American Revolution sights around Boston, Cambridge, Lexington, and Concord. See where the revolution began on a tour that will bring to life the places and characters you learned about in school. Save yourself the hassle of catching public transport or walking by touring with a private driver and car.

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.