Top Massachusetts Private Sightseeing Tours - page 2

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.

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.

Get ready to visit one of the greatest vacation spots in the USA, a favorite among celebrities and even presidents! Martha’s Vineyard is home to stunning beaches and coastline, picturesque little towns, and plenty of fun—but this GPS-guided driving tour with walking portions will also dig beneath the beautiful surface and into the island’s surprising history. Learn about the Wampanoag, the origin of the Vineyard’s famous “gingerbread houses,” and the lost language invented by the island’s residents! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.

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.

Experience the epitome of luxury with our private helicopter tour of Boston. Discover a world of wonder as you soar above the ever-evolving skyline and breathtaking surroundings of this vibrant city. From the moment you arrive, our pilot will cater to your every need, ensuring an unforgettable journey that is tailored exclusively to you. Sit back, relax and capture stunning photos, and prepare to be amazed as you ascend into the skies. Witness the majestic Downtown Boston, the shimmering Seaport District, and the harmonious blend of nature and urban life at Boston Common. Marvel at iconic landmarks like the Hancock Tower, Prudential Tower, and Zakim Bridge, while soaking in the beauty of Boston's renowned park. Whether you're marking a special occasion or seeking a truly immersive escape, our helicopter tour promises an engagement with Boston that transcends the ordinary. Book now and let us elevate your adventure to new heights of opulence and wonder.

Salem and Boston have been home to such a diverse range of historical events that it can be tough to take it all in on your own. On this full-day private tour, join your guide and discover the region’s Puritan history, learn about the 17th-century witch hunt hysteria, hunt for ghosts at several historical local landmarks, and much more.

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.

Explore Boston at your own pace with this hop-on hop-off trolley tour. Visit landmarks like Faneuil Hall, the Boston Tea Party Ships and Museum, and the Prudential Center, while enjoying insights from engaging guides. With flexible routes, discounted attraction admissions, and trolleys departing regularly, this tour is the perfect way to experience Boston’s history and charm.

Maximize time in Boston with this private sightseeing tour focused on city history. Meet your guide in the morning and set out on a city stroll that includes top historic landmarks including Boston Common, Paul Revere’s House, and Faneuil Hall Marketplace. Learn about American history along the Freedom Trail and taste some of Boston’s best food during this full-day private tour.

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.

Try a unique alternative to a typical night out in downtown Boston with an exciting dinner cruise along the city’s waterfront. This expedition on Boston Harbor features a meal with live entertainment and dancing. Watch the sun set, then take a stroll under the stars and enjoy the view of the illuminated Boston skyline at night, or head to the dance floor for music and fun in the ship’s nightclub.

Get a comprehensive overview of Boston’s key landmarks during this half-day tour of the city. Combine a walking tour with a driving tour to cover more ground than you would if you just did one. See important sights like the USS Constitution, Old North Church, and the Paul Revere House and learn about the city’s history from your tour guide.

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.

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.

Ready to taste Ptown? Lace up for a 2-hour trek through history and coastal rebel lore. You’ll track the footsteps of Anthony Bourdain and dive into the bohemian scene that made this fishing village the birthplace of modern American theater. Find out where the Provincetown Players launched, where an undiscovered Eugene O’Neill staged his first plays. Alongside O'Neill, trailblazing writers like Susan Glaspell, Edna St. Vincent Millay, and John Reed fueled the town's creative fire. Over the decades, icons like Tennessee Williams, Norman Mailer, and poet Mary Oliver drew inspiration from the salt air, while acting legends like Marlon Brando and Bette Davis graced local stages early in their careers.End your journey at Vorelli's Restaurant, a beloved local classic. Sit back, relax, and reward your feet with the ultimate Cape Cod feast: a massive, chunky lobster roll, a rich, creamy cup of New England clam chowder, and a refreshing non-alcoholic beverage of your choice and a ice cream cone

See the landmarks and highlights of Boston from the water on this sightseeing cruise in Boston Harbor aboard a 1920s-style yacht. Snap photos and enjoy a unique perspective of the harbor, very different than a typical walking or driving tour through Boston. Highlights include the USS Constitution, Bunker Hill Monument, Old North Church, and the USS Cassin Young.

With its centuries of history, it’s no surprise Boston is packed with haunted sights, though they aren’t always easy for visitors to find. On this nighttime ghost tour, follow a guide to some of the city’s most storied landmarks, such as the Granary Burying Ground, Bostom Common, and the Massachusetts State House, and discover the hidden history and spooky sightings associated with each.

Enjoy complete flexibility and explore the parts of Massachusetts that most interest you with this collection of self-guided walking and driving tours. Receive 10 different itineraries and choose the day and time to use any of them. Use offline with GPS and learn about each place as you travel through.

Discover the Concord of writers including Thoreau, Emerson, Hawthorne, and Alcott on a private tour focused on literary history. From Louisa May Alcott’s Orchard House to Walden Pond, you’ll find the real-world places behind stories you love. Offering the option to meet your guide in Concord or at a central location in Boston, this tour can adapt to your schedule and preferences, without the fixed itinerary of a group excursion.

Discover Boston’s rich past and vibrant present on this small-group (or private) walking tour—a relaxed and informative way to get your bearings if visiting the city for the first time. Gain valuable insight from local guide as you explore spots such as Boston Harbor, Faneuil Hall, Beacon Hill, and the Public Garden. As you wander, learn about the city’s Revolutionary roots, architectural gems, and cultural evolution—and get an understanding of what life is like for modern-day residents.

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.

Boston’s North End boasts cobbled streets, historical buildings and trendy Italian-inspired food spots—the latter testifying to its nickname of “Little Italy”. Skip hours of Googling and book a private walking tour with a guide who’ll introduce you to the area’s tucked-away gems and tastiest Italian eats. Delve into back alleys, hear tales of local history, find hidden crime and movie locations you'd otherwise miss, and pause along the way to savor treats such as pasta dishes, cannoli and more.

Enjoy an alternative night out in Boston on a dinner cruise on Boston Harbor, with an all-you-can-eat buffet meal with live entertainment and dancing. Watch the sunset, then admire the view of the illuminated Boston skyline at night or head to the dance floor for music and fun inside the ship’s nightclub. Bring that special someone or a whole group of friends for a night to remember.

Discover some of Boston’s deepest, darkest secrets that lots of tourists miss out on by joining this “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.