Top Boston Private Sightseeing Tours

Lexington and Concord 3 hour private car tour from Boston

3 hoursFree Cancellation

3-Hour Private "Cold Weather- Warm Van" Driving Tour of Boston

3 hoursFree Cancellation

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.

Highlights and History of Boston: GPS Guided Audio Tour

Delve into Boston's shadowy history on this crime-themed walking tour. Led by an engaging local guide, explore sites like the Boston Massacre Site and South Boston Waterfront while hearing gripping tales of infamous mobsters and serial killers. This tour offers a unique perspective on Boston’s history, perfect for true crime enthusiasts and curious travelers alike. With a duration of approximately 2 hours and 20 minutes, this private tour is an intimate experience. The guide can also provide a "director's cut tour" if the guest would like, adding additional stops and stories not included in the public tour. - Discover Boston's notorious crime history through captivating stories - Visit key sites including the Boston Massacre Site and South Boston Waterfront - Ideal for true crime fans and those looking for a unique city experience - Small group size ensures personalized attention from your knowledgeable guide

Private Boston Crime Tour to Uncover the City's Dark Past

2 hours 20 minutesFree Cancellation

Follow a professional historian, concerned about historical accuracy, able to address adults and children alike, in joy and good humor, to discuss the links between France and America. For example… What are the links and controversies between the history of Quebec and New England? Why was a young man of the French nobility, the Chevalier de Saint-Sauveur, assassinated by rebellious inhabitants? How did the “Yankees” overcome their intolerance towards the French to beat the English on their side? How did the Souvenir of the Marquis de La Fayette encourage Americans to fight and fall on the field of honor alongside the Poilus in 1917? How did the 1775 Revolution spread from America to France in 1789, and from France to Haiti, Vietnam, and other struggles for Freedom and Human Rights, and what their consequences today?

French-American Guided Tour of the Freedom Trail, Boston

1 hour 30 minutes to 2 hoursFree Cancellation

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.

Private Day Trip to Salem and Hammond Castle from Boston

7 hoursFree Cancellation

Visit the real locations where the American Revolution began. Stand on Lexington Battle Green and listen to stories about the very first days of the war and the "shot heard around the world". Walk the Battle Road Trail, stage of multiple skirmishes between the Minutemen and the Redcoats and other "treasonous" events. Visit Concord's Old North Bridge, where the Minutemen routed the Redcoats on their march back to Boston! Return to Boston to visit important sights along the Freedom Trail, including the Paul Revere House, Old North Church, USS Constitution (aka Old Ironside), the Bunker Hill Monument - home to the phrase "don't fire until you see the white's of their eyes", and more!

Old North Bridge - location of the "shot heard around the world"

Private Tour of Lexington, Concord, and Boston

7 hoursFree Cancellation

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.

Private Walking Tour of Freedom Trail and Little Italy

4 hours 30 minutesFree Cancellation

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.

Salem Full Day Private Tour from Boston

8 hoursFree Cancellation

Private Day Tour of Salem and Boston

7 hours 30 minutesFree Cancellation

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.

Private Half-Day Driving Tour of Boston and Cambridge

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.

Monica Mercato's Award-winning Italian sub.

Private North End Neighborhood Tour

3 hours 30 minutesFree Cancellation

Boston to Woods Hole & Martha's Vineyard Ferry Private Chauffeur Service

2 hours 45 minutesFree Cancellation

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).

Salem & North Shore Full Day Private Tour from Boston

6 hoursFree Cancellation

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.

Visit Historic Concord on a Private Day Trip from Boston

5 hoursFree Cancellation

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.

Salem half day private tour from Boston

Private 4-Hour Driving & Walking City Tour

Spend a day tracing America's Revolutionary story in Boston, Lexington and Concord without the inconveniences of self-driving, buses and crowds on this private minivan tour. Sit back and view the sights as your driver-guide recounts facts and snippets you may not hear otherwise. Highlights include Boston's Paul Revere's House and Tea Party ships, plus Lexington's landmarks and Concord's gems, including the home of 19th-century 'Little Women' author, Louisa May Alcott.

Full-Day Minivan Tour of Revolutionary Boston, Lexington and Concord

6 hoursFree Cancellation

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.

Plymouth Half Day Private Tour from Boston

Maine's lighthouses, lobsters, and coastal scenery are just a day trip away from Boston, and this private, full-day excursion explores highlights of the state's southern coast. You can enjoy the view as a driver takes care of the details: try a traditional Maine lobster bake, sample blueberry pie, see picture-perfect Nubble Lighthouse, or shop the Kittery Premium Outlets. Trips are priced per-vehicle for up to four or six people, with your choice of a comfortable sedan or SUV.

Boston to Coastal Maine Private Day Trip

10 hoursFree Cancellation

Boston 4 Hour Private Walking Tour Freedom Trail and Beacon Hill

Visit Boston & Cambridge: Private Full-Day Driving Tour

Why Choose Boston Pro's Private Historic Tour? Luxury Experience: Our luxury SUV ensures a comfortable and stylish exploration of Boston's best attractions, including a scenic drive along the picturesque Waterfront. Customized Itinerary: Enjoy the flexibility to customize your tour. Whether it's spending more time at Harvard, MIT, or lingering in the charming streets of Beacon Hill, the itinerary is tailored to your preferences. Photo Opportunities: Our tour is designed for avid photographers. From the iconic Acorn Street to the scenic views along the Waterfront, every moment is a photo opportunity that captures the essence of your Boston experience.

2 to 3 hoursFree Cancellation

Boston City Private Tour

This immersive self-guided bundle brings together three unforgettable experiences: the iconic Freedom Trail, the hidden history of Beacon Hill’s Underground Railroad, and the chilling ghosts that still linger in Boston’s oldest streets. On this unique Boston experience, you’ll explore the city where revolution began, where courage challenged slavery, and where the past refuses to stay quiet. From historic landmarks and hidden alleys to haunted burial grounds and untold stories, each tour reveals a different side of Boston. No schedules. No groups. Just you, your phone, and the stories that shaped a nation. Perfect for travelers who want flexibility, depth, and a truly memorable way to experience Boston.

Boston Bundle Top 3 Self Guided Freedom Trail Tours

5 to 7 hoursFree Cancellation

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Must-Dos in Boston

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What are people saying about Boston

Private Boston, Lexington & Concord Historical Tour

Fran_K, Oct 2026

The Revolution Clarified

This tour was excellent. Our guide drove us throughout Boston, pointing out historical references, weaving the story of the Revolution as he took us to Lexington and Concord. There were a few contemporary places on the itinerary we were not interested in so the tour was not as long as it could have been but we were more than satisfied overall.

Boston City View Bicycle Tour: Historical E-bike/City Bike Tour

Vicki_C, Oct 2026

Costa, our tour guide was...

Costa, our tour guide was great! He was very informative while educating us about the rich history innBoston as we cycled around the city. We learned a lot and he was very entertaining too! The bike ride was fun and easy and Costa did a fine job of keeping us all together and safe throughout our tour.

Boston Private 3-Hour Tour by Car

Karen_J, Oct 2026

Book this tour! Christian is a superb guide!

This private tour with Christian was fantastic! He asks what you are most interested in seeing and takes it from there. He's professional, personable and has extensive knowledge of Boston. We so enjoyed this tour and highly recommend it - you won't be disappointed! I think the stop at Fenway Park was our favorite! These Texans thank you, Christian, for a wonderful tour of your beautiful city.

Private Boston Freedom Trail Walking Tour

Mike_K, Sep 2026

Great private tour . Great Guide.

We were two couples and did a 3 hour Freedom Trail private tour. Two of us had been on previous, similar tours. Two of us had never been to Boston. Our guide, Don Watson, aka James Otis" was absolutely fantastic. He moved in and out of character with ease as we peppered him with a range of questions. He was enthusiastic and so knowledgeable. The three hours seemed to go by very quickly. All four of us agreed that we would do this tour again if we could use Don Watson as our guide.

Private City Tour of Boston and Cambridge

Lindsay_B, Aug 2026

Great Day in Boston with BJ!

This tour definitely exceeded my expectations! We had 3 generations of travelers from ages 7-79 and everyone really enjoyed it. It was all of our our first time in Boston and this was a great activity for our first day. We had BJ as our guide and he communicated with me in advance of the tour and picked us up timely at our hotel. Our first stop was an Italian coffee/pastry shop in the North End. There we talked through a loose plan for the day, but the best thing about this tour was that BJ was totally flexible… There were certain places we wanted to spend more time, and BJ accommodated us, provided interesting commentary and even helping entertain the kids when one was bored and the rest of us were taking a little longer at a site/exhibit. His vehicle was clean, fully functioning and he had parking passes at certain key places allowing us to pack a lot into one day. I would definitely recommend this tour and BJ to anyone visiting Boston! We will talk about this day and the places we visited for years to come. Already want to plan a return trip! :)

Boston Pizza Lovers Food and History Walking Tour

Sarah_R, Jul 2026

Loved the pizza

We had a great time on the Freedom Trail Pizza Tour! The three pizza slices were all delicious and offered a fun variety, and the tour itself was a perfect mix of Boston history and great food. Margot was an excellent host—knowledgeable, engaging, and made the whole experience enjoyable. We’d definitely recommend this tour to anyone visiting Boston!

Boston's Beacon Hill Underground Railroad Audio Walking Tour

Cynthia_O, May 2026

Great little company!!

Unfortunately, didn’t get a chance to go this time but when we’re back in Boston, we’ll definitely check it out!! I was extremely pleased with how professional and kind my communications were with the company. They reached out every step of the way. We had plans to do the Underground Railroad in addition to the JFK library but the day quickly we got ahead of us and we weren’t able to do the railroad. My only disappointment was that the railroad excursion started a little late in the day. I had plans to do the railroad first since our tickets for the JFK Museum wasn’t until noon. Good luck with your business.

Boston Harborwalk & Tea Party Self-Guided Walking Audio Tour

Jennifer_M, Apr 2026

Lovely and informative.

Park at Harbor Garage for this experience, it starts around the N.E. Aquarium. The walk is like a sidewalk thing around the buildings, right against the water and the buildings so it is right against, it curves with the landscape. VERY nice experience. When you get to one of the spots with the app, it automatically tells you about the area which you arrived. Super interesting and a great job/informative.

Boston Private City Tour

Preety_K, Feb 2026

Sam is hands-down the...

Sam is hands-down the best guide we’ve ever had. He went completely out of his way to make sure we had a great time, even adjusting the itinerary on the fly to suit our interests. He knows all the 'hidden gems' away from the tourist crowds and felt more like a local friend than a tour guide. Our trip wouldn't have been the same without him!

Boston's Freedom Trail: A Self-Guided Tour of All 16 Sites

Jenna_P, Dec 2025

Such a great way to...

Such a great way to explore Boston solo! I didn’t want to do a formal group tour and was so impressed with this entire audio experience. I had never done anything like it before and it was so easy to download and use and I loved how the audio would automatically start when I got to the next location.

Boston Sightseeing Tour - a fully-narrated driving tour

Dyan_K, Oct 2025

Fantastic tour w/Peter

Peter was punctual & full of historic information + he was funny. We had a wonderful time with him. He filled us in on all the points of interest, giving us from the time the British and other countries came here all the way through about the 1950s. If we needed to make a stop, he was willing to do that. And all the anecdotal information that you can’t find in a book was such fun to hear.