Top Boston Private Sightseeing Tours - page 6

Boston Freedom Trail Sons of Liberty Mystery Walk

Go on a discovery tour of Boston. Discover the most important and famous locations of the city. Search for the city's treasures with your family or friends. Can you complete the assignments? Will you get the top score in the city? This E-scavenger hunt will give you a fantastic day in Boston. Decide for yourself when you start, pause and end. It's your party only and you'll get to know the city in a unique way. Instructions for starting the tour will be given after booking. You can do this tour whenever you choose.

e-Scavenger hunt Boston: Explore the city at your own pace

3 to 4 hoursFree Cancellation

from $36

This unique walking tour of Boston, led by Jessica Dello Russo, a PhD in archaeology and Context Travel expert, explores the city’s crucial role in the American Revolution. Starting at Long Wharf, Boston’s oldest port, Jessica reveals how the city’s thriving trade and skilled population helped spark independence. The tour highlights acts of civil disobedience and key figures like John Hancock, Samuel Adams, Paul Revere, and Benjamin Franklin. As you walk, you’ll encounter pre-revolutionary architecture from the 16th and 17th centuries, including the historic Chart House and the controversial Faneuil Hall, built in 1742. On this 90-minute tour, you’ll explore key sites from Boston’s revolutionary history. Visit Granary Burying Ground, where American Revolution figures are laid to rest, and learn about the city’s role in the Trans-Atlantic Slave Trade. By the end, you’ll have a deeper understanding of the figures and events that shaped America’s fight for independence.

A Colonial Boston Audio Tour with Context

A Colonial Boston Audio Tour with Context

1 hour 30 minutes to 2 hoursFree Cancellation

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.

from $20

Private Shopping Tour from Boston to Merrimack Premium Outlets

Private Shopping Tour from Boston to Merrimack Premium Outlets

6 hoursFree Cancellation

1.0

from $418

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.

Ramblin' Boston Tours

from $199

In this immersive 4-hour experience, we will discover the best of Both Worlds: Historic Boston and Harvard University. While we explore the legendary Freedom Trail, we will also dive into the hidden gems and prestigious academic life that make this region so captivating. Your journey begins at Faneuil Hall and Quincy Market, where we step back in time to the dawn of the American Revolution. We will visit iconic landmarks including the Old State House, Old South Meeting House, and King’s Chapel. However, we are not staying only in the past. We will also wander through the gas-lit streets of Beacon Hill, home to some of the most beautiful architecture and prestigious history in the United States. This tour is great for history lovers, first time visitors, Travelers who are looking for the most "Instagrammable" spots in the city , Cultural Explorers, multi generational families. Join me to make this day a very special highlight of your travels.

Boston Harvard Half Day Tour

4 hoursFree Cancellation

from $500

Boston did not just witness the American Revolution. Boston started it. On this private 2-hour walk through the historic heart of the city, you will move through the neighborhoods, markets, halls, and streets where ordinary people made extraordinary decisions that changed the world. From the Rose Kennedy Greenway where modern Boston meets its colonial roots, to Faneuil Hall where civic debate has echoed for centuries, to the gold-domed State House standing watch over Beacon Hill, every stop on this tour is a chapter in America's oldest story. Your private guide, fluent in your language, connects the architecture, the streets, and the people to the nation turning 250 in 2026. The tour ends in the Boston Public Garden, America's first public botanical garden, where you can sit, breathe, and let two hours of history settle in. Boston is where it all began. This is how you experience it properly.

Private Walking Tour in Boston - America's 250th Anniversary

Private Walking Tour in Boston - America's 250th Anniversary

from $449

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

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

2 hours 20 minutesFree Cancellation

from $343

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

45 min Private Boston Harbor Islands and Skyline Helicopter Tour

2 hours

Join Captain Riccardo aboard the Trinacria for a Private tour of Boston Harbor & The Harbor Islands. Choices include Sightseeing, Foliage Tours in Autumn or just Cruising. This unique tour is one of the very few available that you & your guests have the boat to yourselves. Most Boston tours are shared. We also allow you to bring your own Food & Beverages on-board, making your trip ultra personalized. We are flexible on pick up locations & are happy to entertain special requests. Book with us & we will do everything we can to exceed your expectations. Tours can last up to 5 Hours depending on activities chosen. Inner Harbor Tours take 2-3 Hours. Plan on being on-board for up to 4 Hours for Lighthouse tours if you choose to see the offshore Lighthouses. We also can preform an Ash Scattering in a burial at sea ceremony for loved ones remains. We attend to filing all required notifications with the US Government free of charge As a reminder Gratuities are not included the price.

from $449

Cruise - Sightsee - Foliage in Boston, on Private Yacht Trinacria

Cruise - Sightsee - Foliage in Boston, on Private Yacht Trinacria

from $2,000

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

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.

from $599

Lexington & Concord Legends: Revolution & Reflection Private Tour

Lexington & Concord Legends: Revolution & Reflection Private Tour

6 hours 30 minutes

from $602

This private ghost walking tour reveals Boston’s darker historical legacy. Evening shadows fall across streets shaped by centuries of change. At the Omni Parker House, stories reflect a refined past with mystery. In Granary Burying Ground, encounter resting places of early American figures. What secrets remain among these ancient stones? The Cathedral Church adds a solemn and spiritual presence. Boston Common recalls moments of public justice and transformation. Architectural landmarks stand silent as history unfolds in the night. Each step reveals a deeper layer of cultural memory. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

Private Ghost Walking Tour in Boston Historic Landmarks

Private Ghost Walking Tour in Boston Historic Landmarks

from $559

This private culinary and historical walking tour reveals Boston’s revolutionary heritage through its enduring food culture. You begin at Quincy Market where colonial trade once shaped daily life. The atmosphere reflects a marketplace tradition that dates back centuries. At Boston Public Market, regional flavors present a refined introduction to New England cuisine. Along the Freedom Trail, each step connects you to defining moments of early American history. What stories shaped the path toward independence? In the North End, culinary traditions reflect generations of Italian heritage. Historic streets preserve both cultural identity and architectural character. The journey concludes near Old North Church where a signal once altered the course of history. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

Private Culinary & Historical Walking Tour in Boston

Private Culinary & Historical Walking Tour in Boston

3 hours

from $669

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

Boston & Cambridge Icons: Private 7-Hour Discovery Tour

7 hours

from $629

This private car tour is a special edition Rev War 250 tour. We've combined a few lesser known, yet hugely significant Revolutionary War sites in Boston, with the main events in the towns of Lexington and Concord in to a half day tour. Starting in Boston we'll take you to sites where very few tours go and give context to events leading up to the outbreak of the war. Then onto Lexington and Concord to see the towns where the "shot heard round the world" was fired. We'll take the same route as Paul Revere, stopping at the most significant sites along the way giving a detailed account of events of April 1775. The itinerary gives the list of sites we'll visit, timings are flexible and the 4 hour tour time includes travel to and from Concord. This tour is perfect for those groups who have limited time available in Boston or groups who have different degrees of interest in the history of that time.

Likely to Sell Out

Revolutionary War Boston Lexington and Concord Tour

Revolutionary War Boston Lexington and Concord Tour

4 hoursFree Cancellation

from $695

Boston is a World Cup city in 2026. Football fans are arriving in one of America's oldest and most flavourful cities. Your private 3-hour culinary walking tour moves through Boston's most historic districts from Blackstone Block to the North End waterfront. Clam chowder arrives at Boston Public Market. A fresh lobster roll follows. Traditional thin-crust pizza comes next in Boston's Little Italy. A dessert closes the tour near the harbour. Your licensed guide connects every flavour to the cultural story of a city built by waves of immigrants who each left their taste behind. The Blackstone Block carries colonial tavern history. The Rose Kennedy Greenway follows former trade routes. The North End speaks Italian. The waterfront smells of the Atlantic. In World Cup year, Boston feeds the world with the confidence of a city that has been doing exactly that for four centuries.

Private Boston World Cup 2026 History Walking Tour

Private Boston World Cup 2026 History Walking Tour

3 hours

from $819

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

Boston to Lexington and Concord Historical Sites Shore Excursion

4 to 8 hoursFree Cancellation

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 $1,044

"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."

Private Boston Day Trip to Plymouth MA

9 hoursFree Cancellation

from $1,090

America turns 250 only once. This is the tour built for that moment. From the streets of Boston to the bridge at Concord where the first shots rang out, this private 6-hour car journey traces the exact geography of revolution. You will walk Harvard Yard, cross the bridge that inspired a poem read around the world, stand at Lexington Green where farmers faced down the British Empire, and step inside Orchard House where Louisa May Alcott wrote the story of a new American family. Your private guide, fluent in your language, connects every stop to the nation that was born here 250 years ago. Private transport keeps the day seamless. No crowds, no waiting, no compromise. This is not a sightseeing tour. This is a reckoning with the places that made America possible. Boston. Cambridge. Lexington. Concord. In America's 250th year, there is no more powerful journey you can take.

Boston America's 250th Road that Made a Revolution Tour

Boston America's 250th Road that Made a Revolution Tour

6 hours

from $1,729

This private historical tour explores landscapes where American independence began. You travel from Boston into regions shaped by early revolutionary action. In Boston, streets reveal the tensions that led to political transformation. Cambridge introduces academic traditions that influenced national thought. At Harvard Yard, historic buildings reflect centuries of intellectual legacy. Lexington Green presents the quiet field where the first conflict emerged. What moment transformed protest into revolution? At Old North Bridge, you stand where resistance took form. Walden Pond offers a reflective setting linked to classical American literature. Orchard House connects you to literary heritage shaped by cultural identity. Private transport allows a smooth journey through these historic regions. Please note: The program and attractions may vary based on booking date/time and crowd conditions, ensuring each visit is a unique experience.

Private Revolutionary Heritage Tour from Boston by Car

Private Revolutionary Heritage Tour from Boston by Car

6 hours

from $1,729

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

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

4 hours

from $2,287

Boston Pizza Lovers Food and History Walking Food Tour

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Top Attractions in Boston

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Attractions

What are people saying about Boston

Cheryl_S, Jun 2026

Although this is a rather...

Although this is a rather lengthy walking tour, it is very easy to do. I am a senior citizen with a neurological condition that affects my ability to walk and I could still easily complete the tour. We stopped at many historic sites and our tour guide, Scotty, was very knowledgeable about each place. The walking pace was also very comfortable. And the pizza was delicious!

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!

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!

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)!

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'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.

Walk the Historic Freedom Trail with Costumed Guide

Janine_B, Oct 2025

Great Tour!

I had some time before my flight and booked this tour for the morning. Despite some light drizzle I loved seeing the city and walking the freedom trail. History was indeed brought to life and I learned so much on this great tour. The tour guide was AMAZING and helpful as well. A must do in Boston.

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.