Top Boston Private Sightseeing Tours - page 3

Get to know about Boston’s haunted past and explore at your own pace on this self-guided walking tour. Use the app on your phone and your headphones to learn about Boston’s historical ghost stories and visit a variety of sites whenever you choose to go. Spend more time at places that are interesting for you.

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.

Boston's best food and history are scattered across its neighborhoods, so we bring them together in one relaxed, private tour. Start in the North End with cannoli and espresso at the city's oldest Italian café, then wander through Little Italy, hearing stories of Paul Revere's midnight ride and the neighborhood's Revolutionary roots, with a view of Old North Church, where the famous lanterns hung. Sample an Italian sandwich from a traditional salumeria, then stroll Beacon Hill, Boston's most prestigious neighborhood, and Boston Common, America's oldest public park. Stop for lobster rolls and New England clam chowder, then take in Back Bay's Victorian streets and the views of Boston and MIT from Cambridge. Finish at Copley Square by the stunning central branch of the Boston Public Library and a view of the famous Trinity Church. Come hungry! Pickup and drop-off anywhere in the Boston area are included (up to 6 guests).

See every site on the Freedom Trail! This walking tour includes all 16 stops on the Freedom Trail, covering historical sites such as the Paul Revere House, Copp's Hill Burying Ground, Old North Church, USS Constitution, Boston Common, Old South Meeting House, Old State House, Bunker Hill Monument and more! Listen to hilarious stories from Boston's past as you learn about the history of the area from a longtime resident, passionate historian, and former city employee. Tour includes a short walk through historic Little Italy.

Take in 16 historic landmarks along Boston’s Freedom Trail on a self-guided tour that offers the flexibility to explore at your own pace. You can access turn-by-turn directions whenever you want, so you can start, pause, and restart the tour on your own schedule. As you follow the Freedom Trail, you’ll hear stories about local history, legendary Americans, and founding fathers and from a Boston insider.

Most ghost tours in a city start at night and go with a big crowd that can hold you back or move too fast. This private self-guided Boston ghost tour lets you explore at your own pace. Gain access to 60+ historic stories and narrations while you stop at popular Boston landmarks.

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.

While there are many areas within Boston where you can experience the city’s revolutionary history, to get a more complete picture, history lovers can visit the real locations where the American Revolution began. On this full-day private tour, head to Lexington and Concord to walk the Battle Road Trail, see where the Minutemen bested the Redcoats, and much more.

Enjoy one of the simplest ways to discover Martha's Vineyard, and leave all the planning and logistics to someone else, on this hassle-free day trip from Boston. Following pickup directly from your centrally located hotel, take a short ferry ride to Martha's Vineyard. Upon arrival, enjoy free time to explore—or upgrade to add on an island tour that visits its highlights. Complimentary snacks, bottled water, and guidebooks are provided during the drive.

Spend a great day in Boston learning about history and exploring all the top attractions! The tour is designed to be fun for the whole family - we have quizzes, we have kid's guides, we have prizes, and we have interactive stops so kids can work off some energy!

I know the secrets that no one else knows. You will go on a small private tour where you will learn the amazing origins of everyday things. Enjoy the stories of the great places where liberty was born, told by an amazing guide and driver who really knows his stuff. I will lead you through the interior of Old Ironsides, the battleground and museum at The Battle of Bunker Hill and the incredible history of Harvard while amazing you with information about Boston that most Bostonians don't even know. We provide better service because unlike big chains, we are local and depend on our guests' satisfaction.

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.

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 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.

This private historical walking tour reveals Boston’s cultural and architectural legacy. You begin along the Greenway where modern design meets the path of early trade routes. Nearby, Faneuil Hall reflects centuries of civic debate and public gatherings. Quincy Market continues this tradition within a classical marketplace setting. Downtown Crossing reveals layers of commercial evolution shaped over generations. Old City Hall presents refined 19th century architecture tied to governance and reform. The State House stands as a symbol of enduring political tradition. In Beacon Hill, narrow streets preserve a distinct Federal style heritage. The journey concludes in Boston Public Garden where landscaped paths reflect early urban design. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

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 perfect blend of Boston's revolutionary history and its vibrant modern pulse! Join me for a sophisticated journey through gas-lit streets and hidden contemporary gems. This isn't just a walk through the past—it’s an insider’s look at the prestige and daily life of the city today.

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.

Explore several stops along Boston’s Freedom Trail—and learn insider stories about the sights, which you wouldn’t encounter on your own—on this private walking tour. With just your guide for company, have more flexibility than regular group tours, and feel free to move at your own pace. As you go, learn all about Boston’s Revolutionary War history, and visit top sights such as Bunker Hill.

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.

Take a break from your Boston city break with this scenic private tour. There's lots of ocean views, rocky coastline, a bit of shopping and even some witch history. We keep this full day itinerary flexible to let you customize the tour but here's a feel for what we'll see. Pick up in Downtown Boston, taking the 60 minute highway drive to Manchester-by-the-Sea, where we pick up the scenic back roads. We'll take a picturesque country road to Gloucester, where we stop to walk along the waters edge to the Fisherman's memorial statue. We'll continue the scenic drive to Rockport, where there's a great collection of cute stores to browse and views to admire. Then drive to Salem, where we have time for a short walking tour around the main sites and historic spots. To finish out the day we'll squeeze in a few more ocean views on our drive back to Boston. We'll stop along the way for lunch (not included in price of tour).

This tour hits the highlights of Boston's most historic districts. You can take this tour anytime between 7:00am and 8:00pm. Once you make the booking, we will provide you with a link to download the app as well as a voucher code for the tour. This tour includes about 2.5 hours of audio, making it one of the most comprehensive self-guided tours available. We cover a wide range of topics from colonial history to the Big Dig public works project that created the Rose Kennedy Greenway only a few years ago. This tour uses the VoiceMap app and is GPS-enabled. The audio is delivered at the right place and time with turn-by-turn directions, meaning that you won't need to keep looking at your phone.

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.

Take a private day trip from Boston to the North Shore, combining coastal scenery with two of Massachusetts’ most distinctive historic sights. Enjoy door-to-door hotel pickup and flexible pacing that lets you explore without group constraints. Travel comfortably while your guide provides context on regional history, architecture, and folklore, with meaningful time for exploration and photos.