Top Massachusetts Private Sightseeing Tours

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.

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.

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 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.

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, planning tools, scenic stops, and local 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.

Cover a lot of ground and get a better understanding of the city of Boston with this private driving tour. In the company of your guide, walk the Freedom Trail and learn about the history of the city. Travel in an air-conditioned vehicle to easily see part of the city beyond the historic center.

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.

Explore Boston in a way that interests you on a private walking tour that can be customized to your preferences. You'll follow a flexible itinerary tailored to include attractions that you want to see, such as Boston Common, Freedom Trail, or Copley Square. If you don't have specific interests, you can leave the itinerary up to your guide. Either way, this is a chance to enjoy Boston's history and charm with a guide all to yourself.

If you want to explore Salem's haunted history without getting lost in the crowd, go at your own pace with an affordable, self-guided smartphone tour. Simply download the touring app to your phone, and start and stop the tour on your own schedule as the pre-recorded narrator shares the history of haunted locales like the Ropes Mansion, Salem Witch House, and Old Burying Point Cemetery, where many witch trial victims were laid to rest.

Explore the chilling history of the Salem Witch Trials on this self guided audio driving tour on our self-guided tour app, which takes you through the key sites of the infamous trials. Visit Proctor's Ledge, the confirmed execution site of nineteen innocents, and we drive by the Rebecca Nurse Homestead (this is often closed with limited hours), the only preserved home of an executed victim. Uncover the stories behind these haunting events as you drive through Salem, Peabody, and Danvers at your own pace, with offline GPS-guided narration enhancing your experience. Perfect for history enthusiasts seeking an insightful and flexible exploration of this dark chapter in American history. - Visit significant sites including Broad Street Cemetery and Gallows Hill - Enjoy a self-guided experience with professional narration - Explore at your own pace, spending 3-5 hours as you choose - Offline access ensures a hassle-free journey through Salem's history

Explore historic downtown Nantucket on a self-guided audio walking tour. Follow a roughly 2-mile route as stories and directions play automatically along the way. Hear how Nantucket rose to prominence as a whaling port, how Quaker families shaped the island, and how its economy and architecture evolved after the whaling era. See landmarks including the Nantucket Atheneum, Straight Wharf, Hadwen House, Greater Light, and Jared Coffin House. Download the tour in advance to use it offline as you walk. Pause anytime for museums, shops, food, photos, or a break, then continue whenever you’re ready. - GPS-triggered narration plays automatically - Approximately 2-miles and relatively flat - Hear about whaling, Quaker history, architecture, and island life - Works offline after download - Explore at your own pace - Pause anytime and continue when you’re ready

Skip walking and sightsee while seated with a guide to provide commentary and recommendations on this private pedicab Provincetown tour. Board your open-air pedicab with your bicycle-pedaling guide and glide around the Pilgrims’ First Landing Park and Commercial Street where you’ll feel the town’s vibe in a way that’s difficult from inside a vehicle. Then, visit dune-backed Herring Cove beach before a drop-off near the Long Point shuttle—handy for continuing your sightseeing. A souvenir Polaroid photo is included.

Explore the coastline of Gloucester and Rockport, Massachusetts, with this self-guided GPS audio driving tour of Cape Ann. Discover the rich history of Cape Ann as you visit iconic sites like the medieval Hammond Castle Museum and picturesque Halibut Point State Park. Learn about the granite industry's fascinating past and the artistic legacy of local painters like Fitz Henry Lane while enjoying stunning views along Route 127 and 127A. This tour allows you to explore at your own pace, making it perfect for families and history enthusiasts alike. - Self-guided tour covering 25 miles of scenic coastline - Visit historical sites like Hammond Castle and Eastern Point Lighthouse - Flexible pacing allows for stops at beaches, museums, and trails - Family-friendly, suitable for all ages and no 4WD required

Walk Salem’s dark past under moonlit streets and learn true stories of witch trials, haunted houses, and restless spirits. A clear, friendly voice leads you through historic places and shares tales that send chills. You start when you want. Pause to read old inscriptions, stand before haunted buildings, or peer down alleys where shadows linger. Visit The Witch House, the Old Burying Point Cemetery, The Custom House, and hidden corners locals whisper about. The guide also shows you secret paths others rarely walk. The tour works without internet. It gives you walking directions, spooky facts, and tips you’ll use again. The audio stays on your phone forever. Download the tour, put on your shoes, and explore Salem’s haunted history—step by step, story by story, at your own pace.

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.

We'll see the sights on Boston's Freedom Trail and get a closer look by leaving the car and walking inside some locations (depends on day and hours of operation for some sites). We'll have time to go aboard the USS Constitution (closed Mondays). A close-up experience in the oldest neighborhoods of the North End, Beacon Hill, School Street, and Charlestown. Look at places of events and the people from different periods of the settlement of Boston, and the American Revolution. If weather isn't favorable, we can revise the walking portions according to your wishes. A favorite stop is Faneuil Hall, the Great Hall Meeting Room and the Ancient and Honorable Artillery Company Museum (hours vary).

Join Your guide Cathy and embark on a captivating journey through Provincetown’s West End, where the sands of time meet the tides of history. This unique walking tour weaves together the stories of ancient homes, weathered wharves, and steadfast lighthouses, all nestled along the shimmering edge of Provincetown Harbor. Designed to feel like a step into a living museum, this tour blends maritime grit, pilgrim lore, and bohemian charm, offering a soulful exploration of Cape Cod’s northernmost tip. This 90 minute walking tour covers about .5 mile along the West End of Commercial Street. Each stop pulses with Provincetown’s unique blend of history, art, and seafaring spirit, making this tour a love letter to a town that’s both timeless and ever-evolving. After the tour, opt for a Pedi-cab back to the center of town!

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.

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.

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.

Enjoy a private pickup and ride to historic Salem with your guide. Walk the streets where hysteria once ruled, and learn about the Puritan past that shaped daily life in early New England. Uncover the tragic history of the witch trials during a visit to the moving Witch Trials Memorial. Discover Salem's prosperity during the "Old China Trade," when ships sailed to Asia and returned with exotic goods like silk and porcelain, making it one of the wealthiest towns in the early United States and home to the country's first millionaire. See how this era shaped the city beyond the witch trials with a visit to the Salem Maritime National Historic Site. You'll have 1.5 hours of free time to grab lunch and browse for souvenirs, from classic mementos to mystical finds like tarot decks and potion ingredients. Afterward, we'll continue exploring Salem's landmarks before your private ride returns you to Boston.

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.