Top Boston Private Sightseeing Tours - page 6

Providing casual, private, customizable walking tours of the historic Charlestown neighborhood of Boston, including the Navy Yard, home of the USS Constitution and the Constitution Museum, Winthrop Square, the Bunker Hill Monument and battlefield, the Bunker Hill Museum, and the Warren Tavern, established in 1780 and one of the oldest taverns in America. Your tour guide, Tom, was born in Massachusetts and is a 30-year resident of Charlestown. He's the author of a companion book, "Monumental Man: The Life of Solomon Willard, the Architect and Superintendent of the Bunker Hill Monument, " available on Amazon. He is also a licensed US Coast Guard captain, offering tours of Boston Harbor on the 31-foot sailboat "Triple Trouble II," available through the Boatsetter website.

Special Offer

Comfortable Roundtrip Tour from your hotel in Boston to Merrimack Premium Outlets - plays host to luxury boutiques and stores selling everything from clothes and accessories to cosmetics and home essentials. Its world-class boutiques showcasing collections from prestigious local and international designers make for a truly memorable shopping experience. Add to all these a unbeatable prices, and a handful of trendy cafés and restaurants, and what you’ll get is one of the best shopping destinations in and around the Boston. After you finish your shopping you will be picked up and will be delivered directly to your hotel in Boston. All our vehicles are fully licensed and insured. We are happy to provide child seats in our cars for all ages upon request. Vehicles are clean inside and outside; our drivers are well-dressed and unfailingly attentive to our guests. They speak English. They will greet you with a name sign and will help with luggage.

Ramblin' Boston Tours

Free Cancellation
4 hours

Private Shopping Tour from Boston to Merrimack Premium Outlets

Free Cancellation
6 hours

from $423

Step into Boston’s darker side on a private ghost walking tour where you lead the way through centuries of legends. With your guide at your side, you move from the glowing façade of the Omni Parker House to the silent stones of Granary Burying Ground and the Cathedral Church of Saint Paul. You cross Boston Common, once a site of executions, and pause by the refined exterior of the Boston Athenaeum before finishing near the imposing John Adams Courthouse. At every stop, you choose how close to stand, what to photograph, and which stories to ask more about. This night, the city’s most haunting tales are told just for you. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

Mysterious Ghost Private Walking Tour in Boston

Free Cancellation
2 hours

from $478

This private 45 minute helicopter experience offers an intimate and elevated way to explore Boston’s Skyline and Harbor Islands. Enjoy sweeping aerial views of historic landmarks, sandy beaches, and the city’s iconic waterfront, all from the comfort of a private helicopter. Your pilot provides relaxed, personalized commentary throughout the flight, creating a calm, unhurried experience tailored to your interests. With unobstructed views and plenty of time for photos, every moment is designed to feel special. After landing, unwind in our private lounge with complimentary refreshments before continuing your day. This experience is ideal for couples, families, and guests celebrating something special! Experience highlights - 40-45 minute private helicopter tour over Boston’s skyline and Harbor Islands - Personalized and private experience with an experienced pilot - Stunning aerial views and great photo opportunities - Access to a private lounge with complimentary snacks and drinks

45 min Private Boston Harbor Islands and Skyline Helicopter Tour

2 hours

from $449

Witness the stunning transformation of Boston as the sun sets during this popular helicopter tour. Soar above the Boston Harbor Islands and the iconic skyline, capturing breathtaking views of the vibrant city and serene ocean from the sky. Trusted by thousands of guests and backed by over 1,000 five-star reviews, this experience is carefully designed to capture THE BEST sunset over Boston. Your skilled pilot will ensure a personalized experience, while you enjoy opportunities to take incredible sunset photos. After your flight, relax in our lounge with complimentary snacks and beverages while you digest the INCREDIBLE views. - 45-minute sunset helicopter tour over Boston’s Skyline and Harbor Islands - Private helicopter experience - The only way to experience a west-coast-style sunset as the sun sets directly behind Boston’s skyline. - Enjoy complimentary refreshments in our lounge - Incredible golden-hour and sunset photo opportunities

Sunset Premium Helicopter Tour Over Boston with Pickup Option

2 hours

from $599

Step into the pages of American history on this private 6.5-hour day trip from Boston to Lexington and Concord—the legendary towns where the American Revolution began. With a passionate local guide and comfortable private transport, you’ll explore battlegrounds, colonial taverns, and historic trails that tell the dramatic story of the nation's birth. But that’s just the beginning. In the second half of the tour, you’ll shift from muskets to manuscripts as you explore Concord’s literary legacy, visiting the homes, graves, and favorite haunts of great American authors like Louisa May Alcott, Thoreau, and Emerson. It’s a perfectly balanced journey of history, nature, and culture—crafted just for you.

Lexington & Concord Legends: Revolution & Reflection Private Tour

6 hours 30 minutes

from $609

Step into the storybook of American history on this 7-hour private tour through the iconic streets of Boston and Cambridge. From the cobblestones of Beacon Hill to the hallowed halls of Harvard, this experience blends revolutionary history, architectural beauty, and vibrant culture into one unforgettable day. Led by a knowledgeable guide and traveling in a comfortable, air-conditioned minivan, you’ll explore historic landmarks, charming neighborhoods, and world-renowned universities. With coffee and a cannoli to start your morning, and plenty of stops for photos, exploration, and a relaxed lunch, this tour is the perfect way to get to know the soul of New England.

Boston & Cambridge Icons: Private 7-Hour Discovery Tour

7 hours

from $636

Skip the crowds—this is a private tour for your group only! Step into history and flavor on Boston’s Culinary & History Walk, where the revolutionary past meets mouthwatering present. Start at Quincy Market, where colonial echoes mix with vibrant food vendors. Follow the Freedom Trail as each stop reveals stories of courage, rebellion, and the spirit of America’s founding. Then, delight your senses in the North End, Boston’s oldest neighborhood, with authentic Italian dishes that reflect generations of tradition. This isn’t just a walk—it’s your personal journey through time, taste, and tales. Discover legendary landmarks, indulge in local flavors, and experience Boston in a way that’s rich in history and deliciously unforgettable. Note: Itinerary and attractions may vary depending on the date, time, and crowd conditions—making each tour a unique and special experience.

Likely to Sell Out

Private Culinary & Freedom Trail History Walking Tour in Boston

3 hours

from $651

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).

Boston Freedom Trail Private Car Tour

Free Cancellation
4 hours

from $656

This private car tour is the perfect way to see Boston & Cambridge in a half day. You'll get to see all the sites on the Freedom Trail, pausing at some of the city's most significant sites. We'll drive in and out of the other city neighborhoods, Beacon Hill, Back Bay and Seaport and finish out the Freedom Trail with a stop at Bunker Hill. Then it's across the Charles River to Cambridge, where we drive around the MIT campus, and onto Harvard for the history and significant buildings on the campus of the oldest college in the country. We'll share lots of history and legends but also keep it topical with current day fun facts and light hearted stories. All guides are fully licensed and approved Boston tour guides, driving luxury and livery insured vehicles. Downtown Boston pick up and drop off included.

Boston and Cambridge 4 Hour Private Driving Tour

547

Free Cancellation
4 hours

from $695

90min BYOB Boston Harbor Cruise. Pedal as much as you want or just relax and enjoy the amazing harbor views. Bring Your Own Beverages, Food and Music. We provide coolers with ice in our high center bar and Bluetooth connectable speakers. Great for unique fun Birthday and Bachelor/Bachelorette Parties, Outings with Colleagues, School Field Trips or just an amazing time with friends and family. We cruise close to shore at slow speed to get close up views of the harbor attractions and provide a QR code connectable Interactive tour route app with a wealth of information on 36 points of interest that you will pass. Charter groups can chose from 7 boarding locations upon request. Charters can be booked from 10AM to 8:30PM, 7 days per week, mid-April through October.

Cycleboat Boston 90 min BYOB Amazing Harbor Private Charters

Free Cancellation
1 hour 30 minutes

from $949

Visit historic sites in Lexington and Concord. Focus on sites related to the start of the War of Independence, early years of the towns, and authors of 19th Century Concord. Experience scenic countryside, town centers and Walden Pond Reservation. We can customize this tour to specific interests and to other locations in Lexington and Concord. Your guide is licensed by the town of Concord.

Boston to Lexington and Concord Historical Sites Shore Excursion

Free Cancellation
4 to 8 hours

from $990

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to the heart of the city. Upon your arrival, meet your seasoned tour guide, ready to lead you on an enchanting tour of Boston and Cambridge. Discover the awe-inspiring allure of Caffe Vittoria, marvel at the grandeur of North Square Park, and capture iconic moments at landmarks like Old North Church & Historic Site, Copp's Hill Burying Ground, Paul Revere Mall, and many more. Our excursions are meticulously designed schedule. We'll greet you directly at the hotel and ensure you return with ample time to relax and relish your day. Leave the details to us as we escort you on an extraordinary adventure, crafting memories that will stand the test of time!

Private Tour Boston and Cambridge

9 hours 40 minutes

from $1,056

"Embark on a private day trip from Boston to Plymouth, MA, and delve into the profound history of one of New England's most important locales. Begin your journey at Pilgrim Memorial State Park, where the storied Plymouth Rock marks the Pilgrims' landing. Aboard the Mayflower II, a detailed replica, learn about the 1620 voyage. The Plimoth Patuxet Museums offer a lively reenactment of 17th-century life; engage with costumed interpreters and savor a traditional meal at the café. Discover the Pilgrim Hall Museum, the nation's oldest public museum, featuring an array of real Pilgrim artifacts. Stroll along Plymouth Harbor for beautiful views. The tour concludes at the towering National Monument to the Forefathers, before allowing some free time to explore downtown Plymouth's charming shops, galleries, and cafes. This tour not only traces the historical tapestry of Plymouth but also offers a deeply personal connection to America’s foundational stories."

Likely to Sell Out

Private Boston Day Trip to Plymouth MA

Free Cancellation
9 hours

from $1,090

A quick helicopter charter from Boston to Chatham offers a unique way to explore Cape Cod. Enjoy a scenic flight along the Massachusetts coastline, avoiding over three hours of traffic while landing in the charming heart of Chatham. Spend four hours discovering boutiques, dining, and relaxing on the beach before returning. This private flight experience includes personalized customer support and the option to extend your stay. Perfect for couples, friends, or small groups seeking an unforgettable day trip.

Cape Cod Helicopter Day Excursion

4 hours

from $1,199

Likely to Sell Out

A private journey leads you through the birthplace of American independence. You travel from Boston to Lexington and Concord and explore peaceful sites where the first moments of the Revolution began. You stand on Boston’s historic streets and hear stories about early protests. You arrive on Lexington Green and feel the calm field where the first shots changed history. You walk near the Old North Bridge in Concord and sense the strong spirit of the past. You enjoy a quiet moment near Walden Pond where classic literature took shape. You explore Harvard Yard and admire the energy of student life. Private transport allows you to move smoothly between Boston, Lexington and Concord. A local guide shares clear stories that help you connect each place with its meaning. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

Revolutionary Tales Private Tour: Boston, Lexington & Concord

6 hours

from $1,303

Enjoy a private, exclusive tour with your own local guide. Heard of Harvard, MIT, and many more historical landmarks on the East Coast? Time to experience history. You will take a sneak peek into the startup nature at MIT’s campus. Drop by Harvard to explore the high-end of the US education system. Driving along Tory Row, our local guide will tell you the secrets of the American Revolution. Now, what is so special about Lexington Battle Green It’s the site where the first bullets were fired that ignited the revolution. Hancock Clarke House and Paul Revere’s capture site has its own tale of heroes. The first men to take to arms are talked about at the Minutemen National Park. We’ll end the tour by passing by Concord’s Old North Bridge, which spans the 26km historic Concord River.

Cambridge, Lexington and Concord Private Half-Day Tour by Car

4 hours

from $2,314

Boston Private 3-Hour Tour by Car

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Top Attractions in Boston

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What are people saying about Boston

Katherine_F, Apr 2026

Don't hesitate to book!

Joan was the best! We had a great time cruising around Boston, and learned a ton. It was a wonderful combination of historical facts and fun. Doing a private tour let us ask all kinds of questions and have the tour fully customized. Joan was flexible with where she dropped us off at the end too. My 12 year old son said it was his favorite part of our trip to Boston! Highly recommend!

Lexington and Concord 3 hour private car tour from Boston

Clinton_E, Mar 2026

A highly recommended, brilliant tour!

We absolutely loved our tour of Lexington and Concord with Martin, the best tour guide in New England! He picked us up from our hotel right on time in a clean, new minivan. He gave us a brief photo review of the land-filling that created the Back Bay (as our hotel was there). He then gave us a drive-through bonus tour of a bit of MIT and Harvard on the way to Lexington. We were able to briefly walk the long corridor of MIT and see the unbelievable freshman dining hall at Harvard. Both on the road and when out of the van in Lexington and Corcord, Martin demonstrated a captivating style of history telling that really intrigued the listener. He is clearly passionate about the details of the events of April 19, 1775. I was easily able to visualize the incredible drama that unfolded in these towns on that day. Because of this, standing on Lexington green was very moving for me. Near the end of our tour, he gave us a bonus drive-by of Bunker Hill and provided us with some additional history. He then walked us in to the Warren Tavern, so to insure that we found a great seat. This was my fifth or sixth trip to Boston, and can say without hesitation that this or any of Martin’s company’s tours will stand above the rest (we also took the full-day private tour of Salem and the coast with Martin)!

Private 4-Hour Walking and Driving City Tour

Clinton_E, Mar 2026

Outstanding overview of Boston!

We thoroughly enjoyed our 4-hour Boston overview with an amazing guide, Neal! The tour was a well-balanced mix of walking and riding. We saw so much in 4 hours! Neal clearly has a passion for his city, and this made for a fun, interesting, and educational experience. Even though I have been on a few tours of Boston in the past, he still introduced us to several new sites and many new facts! He recommend several great restaurants that we would have never have explored if not for him. Ask him for some “cash only” recs!

Boston Freedom Trail Self-Guided Tour with Audio Narration & Map

Chris_B, Mar 2026

Great storytelling - get two for one!

Great narration throughout the tour. The tour tracked our location using GPS and automatically started the narration as we approached different stops. Pro Tip: For two people, just buy one tour and each of you can wear an earbud for the tour...two for one!

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!

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

Giulio_M, Dec 2025

The absolute best way to see Boston—Peter is a legend!

If you are looking for the perfect way to see Boston without battling the freezing temperatures, this is it. Our group of four booked this tour on a whim, and it ended up being the highlight of our trip. The 'warm van' promise was fully kept, but the real star of the show was our guide, Peter. I cannot speak highly enough of him. Often, a three-hour drive can feel long, but Peter kept our attention the entire time. He has an endless supply of fascinating stories and local history that you simply wouldn't get from a guide book. He managed to make the city come alive while we stayed perfectly comfortable. If you want a tour that feels personal, engaging, and incredibly comfortable, ask for Peter. Worth every cent!

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.

Private City Tour of Boston, Lexington, and Concord

James_S, Oct 2025

Great way to see Boston and area in a short time!

Although this is not the cheapest way to see the Boston area, it is by far the best if you want to see a maximum amount in a minimum time in great comfort! It was just myself and my husband for 6 hours, but it would be cheaper if you have more people to split the cost. Being chauffeured around by Sam was wonderful! He is so affable, knowledgeable and flexible and made our tour a total pleasure! He picked us up and returned us to our Waltham suburban Boston hotel which was very convenient. You can arrange this tour to your liking and stay at any given place as much or as little as you like. I highly recommend this tour and ask for Sam!

Highlights of Boston Private Tour

Lisa_Y, Sep 2025

It was a private tour and...

It was a private tour and Marybeth was excellent and met on all our requests above and beyond. We went passed Harvard university and MIT…heard many stories about the campus and the Great Dom Hack about Harvard’s plank. We drove by Italian town and Chinatown. Ate at the famous Cheers and was delicious. We had a non walking tour as requested…mainly drove around town.

Downtown Freedom Trail, Beacon Hill & Back Bay Walking Tour

Sara_S, Jun 2025

Tour Guide Alan was...

Tour Guide Alan was knowledgeable and friendly. The tour itself had a variety of walking surfaces that may be hard for people with mobility issues. It was cold and windy that morning so be sure to check the weather and dress appropriately. We found the tour to be full of interesting information and sights.