Top Boston Private Sightseeing Tours - page 3

Boston to Coastal Maine Private Day Trip

10 hoursFree Cancellation

Boston Massachusetts Private Photography Tour

1 hourFree Cancellation

Boston's 250th Freedom Trail Tour

1 hour 45 minutesFree Cancellation

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

Enjoy a private, customizable day trip from Boston to Newport in a comfortable vehicle reserved for your group. This is private transportation with flexible sightseeing stops; the chauffeur does not provide guided commentary. Visit one, two, or up to three Newport mansions based on your tickets, entry times, attraction hours, and preferred pace. Most guests visit two mansions, stop for lunch, then choose a third mansion or another Newport attraction. When time allows, options may include downtown Newport, Ocean Drive, or a brief Cliff Walk stop. Your chauffeur handles transportation between stops, so your group can relax without navigating traffic or parking. All customization must fit within the included 8.5-hour service period and is subject to traffic, weather, attraction hours, and ticket times. To stay on schedule, the return to Boston should begin around 4:00 PM. Mansion tickets and lunch are not included.

Private Newport Mansions Day Trip from Boston

8 hours 30 minutesFree Cancellation

The Ghosts of Boston's Past Haunted Self-guided Tour

30 to 45 minutesFree Cancellation

From seals and sea lions to sea turtles, seadragons, and stingrays, the New England Aquarium is the place to discover hundreds of different marine animals under one roof—or in one big tank. Check out the four-story Giant Ocean Tank, featuring a brand new coral reef, underwater communications system and hundreds of Caribbean reef animals. Grab an admission ticket and have an unforgettable aquarium adventure.

New England Aquarium Admission Ticket in Boston

Boston City View Bicycle Tour: History and Landmarks

2 hours 30 minutesFree Cancellation

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

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

Private All-Inclusive Boston Famous Foodie Tour

3 hoursFree Cancellation

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.

City Cruises Boston Premier Dinner Cruise on Odyssey

2 to 3 hoursFree Cancellation

3.8

(203)

from $133

Travel back in time, to the early years of the United States of America, during this guided walking tour of Boston’s Freedom Trail and beyond. Relive the events of the American Revolution as you pass Faneuil Hall, see the Old and New State Houses, and visit the setting of the infamous Boston Massacre. Then head downtown past Boston Common and the modern John Hancock Tower, finishing in Copley Square.

Downtown Freedom Trail, Beacon Hill & Back Bay Walking Tour

Downtown Freedom Trail, Beacon Hill & Back Bay Walking Tour

Boston Walk Through History Private & All-Inclusive Tour

3 to 6 hoursFree 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

4 hoursFree Cancellation

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.

Private Historical Walking Tour in Boston Cultural Landmarks

Private Historical Walking Tour in Boston Cultural Landmarks

Private Tour of Boston for Families & Kids

4 hoursFree Cancellation

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

2 hours 45 minutesFree Cancellation

Boston Private Day Trip with Salem & Cape Ann’s North Shore

Explore the city of Boston in comfort on this private driving tour that covers the main attractions and highlights. Perfect for those who are short on time but want to see the sites, this tour features a stop at the Freedom Trail, which includes Kings Chapel, Old South Meeting House, the Old State House, Paul Revere’s House, and Boston Common. Then, visit Bunker Hill and learn how the battle here impacted the Revolutionary War.

The Best of Boston: Private Half-Day Highlights Driving Tour

The Best of Boston: Private Half-Day Highlights Driving Tour

Full-Day Private Tour of Boston with Pick Up

Special Offer

6 hoursFree Cancellation

Discover some of Boston's most notable historic landmarks—and pair your sightseeing with a pizza crawl—on this time-saving, two-in-one walking tour. With just a guide and small group for company, stroll through the city’s oldest neighborhoods, including Little Italy on the North End. Walk along the Freedom Trail to sights including Paul Revere House and the USS Constitution, and head to local pizzerias for three full-size slices along the way.

Boston Pizza Lovers Food and History Walking Tour

Boston Pizza Lovers Food and History Walking Tour

2 hours 30 minutesFree Cancellation

Private 4-Hour Driving & Walking City Tour

Discover Boston’s famed Freedom Trail on a private walking tour through the city. Follow your dedicated guide past key landmarks including Paul Revere’s house, Old North Church, Boston Common, Faneuil Hall, and much more, customizing the tour to your group’s interests. While you walk, your guide regales you with information about Boston’s history with particular emphasis on the American Revolution and independence.

Private Walking tour of Boston's Freedom Trail and more!

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Must-Dos in Boston

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What are people saying about Boston

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.

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 3-Hour Tour by Car

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!

Salem half day private tour from Boston

Joan_A, Mar 2026

Fantastic tour!

If you’re visiting Salem, do yourself a favor and take a tour with Martin. Our experience was absolutely fantastic and easily one of the highlights of our trip. Martin led a guided tour of Salem that was both incredibly informative and genuinely entertaining. He showed us six filming locations from Hocus Pocus, which was a really fun addition, and also brought us to the iconic Bewitched statue. Beyond the pop culture stops, his in-depth knowledge of the Salem Witch Trials was impressive—he explained the history in a way that was engaging, thoughtful, and easy to understand. He also made a stop at the oldest candy shop in the United States, which was such a unique and memorable part of the tour. It’s clear Martin truly knows Salem inside and out. What really set the experience apart, though, was how much he went above and beyond. At the end of the tour, he even helped us secure reservations at a restaurant so we could relax and enjoy the rest of our evening without worrying about finding a place to eat. Martin clearly cares about making sure people have a great experience in Salem (and other areas in and around Boston), and it shows in every part of the tour. If you’re looking for a guide who is knowledgeable, personable, and passionate about the history of the area, Martin is the one to go with. Highly recommend!

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!

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.

Best Boston Private Tour, I know the secrets others don't!

Steven_S, Oct 2025

Custom tour of landmarks and hidden gems of Boston

We had an incredible day exploring Boston with our private guide, Stewie. Having visited the city before and walked the Freedom Trail, we appreciated that this tour was customized to highlight places we hadn’t seen—hidden gems alongside iconic landmarks. Stewie, a true local, brought the city to life with his deep knowledge and colorful anecdotes at every stop. Our itinerary included some of Boston’s most memorable sites: Harvard’s historic campus, the charming streets of Beacon Hill, Bunker Hill Monument, Old North Church, Fenway Park, the Old State House, and the quirky All Saints Way. We also enjoyed a delicious lunch at Table Mercato, a cozy Italian deli that hit the spot. Stewie went above and beyond, even helping with our luggage at pickup and ensuring a smooth drop-off at our hotel.

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.