Top Boston Private Sightseeing Tours

Discover Boston’s rich history, iconic landmarks, and vibrant neighborhoods on a private sightseeing ride with your English-speaking Welcome Driver. Begin at Boston Common, then explore the charming streets of Beacon Hill and admire the Massachusetts State House. Continue to Quincy Market & Faneuil Hall and the historic North End, where colonial heritage, lively public spaces, and local culture come together. Enjoy a flexible itinerary with time for photos, short walks, or coffee breaks along the way. Later, visit the Charlestown Navy Yard & USS Constitution Viewpoint before strolling along the Boston Harborwalk, where waterfront scenery and Boston’s maritime history provide a memorable finish. With private transportation, local insights, and a relaxed pace, this experience is the perfect introduction to one of America’s most historic cities.

Forget the crowded hop-on, hop-off buses and rushed group tours where you're just another face in the crowd. Picture Boston is a completely different kind of city experience — intimate, immersive, and carefully curated for people who want to feel this extraordinary city truly. Fully narrated by one of Boston's own expert local guides, you'll glide through neighborhoods rich with history, step out at the city's most photogenic corners, and leave with both a deeper understanding of Boston — and a camera roll that will leave your friends speechless. Whether you're visiting for the first time or rediscovering the city you call home, Picture Boston will show you something you've never seen before.

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.

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.

It can be tough to take in all of Boston’s historic sights on your one in just one day, so this private combination car and walking tour of Boston and Cambridge is here to help. Follow in the footsteps of famous academics exploring Harvard and MIT, learn about Boston’s storied history and the American Revolution at Beacon Hill and the Bunker Hill Monument, and explore the artisanal food options available at the US’s oldest tavern and restaurant.

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.

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've always wanted to see Plymouth Rock, this 4 hour tour lets you check it off the bucket list. It can fit snuggly into a Boston city break without using up too much of your time in the city. We pick up in downtown Boston and travel 50 minutes directly to Plymouth. There we'll do a walking tour around the town, explaining why the Pilgrims landed here and how they settled in to the area. Go aboard the Mayflower II (seasonal) to see for yourself how awful their journey must have been and stop by the memorial for the legend of the rock. Quick stop at an impressive monument, built to honor the Pilgrims and then it's back to Boston. Boston is 50 minutes drive from Plymouth, so you will be in the car a chunk of time on this tour. You will have approximately 2 hours in Plymouth.

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.

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.

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.

If you've always wanted to visit this infamous town, then let's do it during your visit to Boston. This half day Boston to Salem tour consists of: - Downtown Boston pick up, ~45 minute drive to Salem - Stories of what happened before, during & after the Salem Witch trials - Walking tour of movie scenes, sites and fun facts of Salem - Go into one of the main Salem attractions (entry fee not included, and availability not guaranteed) - 45 minute drive back to Boston If you'd rather skip going into any of the sites, we use that time to take you to Marblehead for some amazing ocean views. The return journey and tour is 4 hours, we're happy to customize it to accomplish the things you're most interested in.

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).

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.

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.

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.

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.

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).

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.

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.

Relive one of the most important events leading up to the American Revolution and learn about a side of the story most tourists miss on this guided tour of the Boston Tea Party Ships and Museum. Explore authentically restored tea ships with the help of a guide as you get their insights into this pivotal event, and throw some of your own tea into Boston Harbor. It's an ideal experience for American history buffs, tourists, and locals alike.

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.

Discover Boston, Salem, and Cape Ann with maximum flexibility using this self-guided audio tour. Location-based narration shares colorful local history as you explore—it’s all at your own pace, which means you can stop and start the guide as you pause to take photos, eat lunch, or take breaks. Since the self-guided tour uses offline maps, it even works without cell service or WiFi.

Discover a whole new side of baseball history with the help of a guide on this tour of Fenway Park, one of baseball’s most beloved stadiums. 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. It’s ideal for baseball fans, be they locals or tourists.