Top Boston Historical Tours - page 9

Boston Revolutionary War: At your own pace. An audiovisual walking tour.

2 to 3 hoursFree Cancellation

Astounding Scavenger Hunt: Boston The Story of America

Astonishing Scavenger Hunt: Boston Back Bay & Beyond

An Epic Scavenger Hunt: Boston Parks & Works of Art

Boston can sometimes feel inaccessible to foreign visitors. Take the mystery out of your visit by exploring with a local on a private walking tour. This is a personalized experience where you will discover the exterior of monuments, including museums. If you would like to include a museum visit, your guide can create a customized itinerary—just let us know in advance. Your guide contacts you beforehand to understand your interests, ensuring you see only the places you want. As you explore, enjoy insider insights into Boston’s culture, history, and hidden gems, forming a richer connection to the city that you won’t get on your own.

Private Walking Tour with a Local Guide in Boston

3 hoursFree Cancellation

Price varies by group size

Walking Tour The best of Boston

4 hoursFree Cancellation

Private 4-Hour Walking Tour in Boston with Official Tour Guide

4 hoursFree Cancellation

Price varies by group size

Boston's Freedom Trail Self-Guided Walking Audio Tour

3 to 4 hoursFree Cancellation

Special Offer

Step into the heart of Boston’s past with our Beacon Hill Walking Tour —your self-guided audio companion through one of the city’s most historic and picturesque neighborhoods. Wander charming cobblestone streets, admire gas-lit lanterns and stately brownstones, and uncover the stories of abolitionists, authors, and revolutionaries who once called this area home. With expert narration and total flexibility, you can explore at your own pace—no tour groups, no schedules, just your own personal guide in your ear. Download now and let Beacon Hill’s history unfold as you go! *Download the Shaka Guide app to access the purchased tours*

A Private Self Guided Walking Tour in Beacon Hill

4 to 5 hoursFree Cancellation

Local Bostonian and Historical Driving Tours

1 to 3 hoursFree Cancellation

Learn about Boston’s deep history in the abolitionist movement while exploring the cobblestoned, winding streets of Beacon Hill – one of the most photogenic neighborhoods in America. You will see 50 important Underground Railroad sites that made historic Boston the “cradle of equality.” Experience what life was like for historic Black Americans, many of whom shaped the future of the city and the nation. Tour guide is a local Beacon Hill resident who has been working as a photographer/videographer in downtown Boston for 10+ years. Wear your walking shoes and be prepared to take some beautiful pictures!

Historic Underground Railroad Walking Photo Tour w Local Guide

This small-group tour stands out by offering an intimate, authentic experience, allowing guests to connect more deeply with Boston’s local stories. With a focus on personal attention, our passionate local guides share not just historical facts but real, untold stories of the city, making each stop feel unique. The small group size ensures a more personalized experience, giving you the chance to ask questions, interact, and truly immerse yourself in the heart of Boston’s history. It’s more than just a tour—it’s a genuine journey through the city’s past, told by the people who live it.

Freedom Trail and North End History and Culinary Delights Tour

4 hoursFree Cancellation

Have some PRE-GAME Fun before the big game at Fenway Park! This unique food tour starts at Old City Hall in Boston, which was the original sire of Boston Latin; the 1st public school in America. From here, you'll walk, learn, eat & drink your way through historic Boston Common and the Back Bay neighborhood toward Fenway Park. Top-notch food stops may include a slice from Boston's only "vera pizza Napoletana", wagyu beef sliders at a delicious Back Bay eatery, chicken wings at a hot-spot for Locals, and finish with a classic "Fenway frank" outside the Fenway Park. This fun & unique food tour finishes approximately 30-minures prior to game time, with photo-ops at some of the most famous statues of Red Sox Legends like Ted Williams, Carl Yastrzemski and Joe DiMaggio.

Fenway Park’s Ultimate Food Crawl: Bites, Bases & Pre-Game Fun

2 hours 30 minutesFree Cancellation

Skip the line and journey through 5,000 years of art at Boston’s Museum of Fine Arts. See masterpieces by Van Gogh, Monet, and ancient treasures from Egypt to Asia. Discover one of America’s finest museums, rich in history, beauty, and culture. Highlights: • Visit the renowned Museum of Fine Arts with a 5-Star Licensed Private Guide • Skip the queue with our exclusive skip-the-line tickets to this iconic museum • Discover hidden gems and masterpieces tailored to your artistic interests • Learn fascinating stories behind American art, Impressionism, and ancient Egypt • Explore at your own pace with a fully personalized and interactive experience Step into a world of artistic brilliance with Rosotravel on a Private Tour of Boston’s iconic Museum of Fine Arts. With Skip-the-Line Tickets and a Licensed Guide at your side, enjoy a personalized journey through one of the most prestigious art collections in the U.S. Discover the wonders of Boston with us today!

Museum of Fine Arts Boston Skip-the-Line Private Guided Tour

Price varies by group size

Discover Boston: Self-Guided Audio Tour

5% savings

from

$15$14

This private day tour is the perfect way to get to know Boston & Cambridge at a leisurely pace. It's a combination of walking and driving (although can be driving only if you prefer). We start with a walking tour of parts of the Freedom Trail, stopping at some of the city's most significant sites. We'll then 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 a walking tour 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. After the walk you'll need some lunch and we know some great spots (not included in price of tour). All guides are fully licensed and approved Boston tour guides, driving luxury and livery insured vehicles.

Boston and Cambridge walking and driving private tour

6 hoursFree Cancellation

Discover the stunning Boston skyline from the unique perspective of the water with customized private boat charters on the Jess~Sea. Whether you're interested in a scenic harbor tour, historical sites like the USS Constitution, or a relaxing picnic on Spectacle Island, the experienced crew will tailor the adventure to your desires. With room for up to six guests, this intimate experience allows for personalized exploration of Boston’s hidden gems. Bring your own food and beverages for a perfect day on the water, all while enjoying expert guidance and local insights. - Private charters tailored to your interests, accommodating up to 6 guests - Explore historical sites, islands, and scenic views unique to Boston - Option to bring your own food and drinks for added convenience - Experienced crew dedicated to creating memorable experiences and sharing insider knowledge

Customized Private Boat Charters in Boston Harbor

1 hourFree Cancellation

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

It is the winter of 1773, and Boston simmers on the edge of revolution. You have just been sworn into the Sons of Liberty and handed a coded cipher. From the steeple of the Old North Church, through Paul Revere's house and the halls where patriots first dared to speak, follow the hidden trail down to the harbour — and uncover the cause the cipher was protecting before the British close in. Blending real Revolutionary history — the Boston Massacre, the Old State House, the Tea Party — with a conspiratorial spy mystery, every stop reveals the true story of the landmark while advancing the intrigue. Augmented reality brings the clues to life on the cobblestones and facades, with audio narration in 32 languages. Start whenever you like, go at your own pace, pause for photos. No guide, no fixed schedule, no app to download — just open it on your phone and play. A perfect blend of sightseeing, storytelling and puzzles for explorers, couples and families visiting Boston.

Boston Freedom Trail Sons of Liberty Mystery Walk

Boston’s revolutionary spirit didn’t emerge overnight. It was forged through years of defiance, from merchants smuggling wine, to ropewalkers brawling with British soldiers. On this walking tour, you’ll find out how everyday acts of resistance transformed colonial Boston into the birthplace of the American revolution. You’ll also uncover the gritty reality behind the propaganda and myths taught in textbooks. The tour starts at Long Wharf, once the longest in the Western Hemisphere, where 4,000 British troops landed in 1768 to discipline a rebellious city. You’ll walk through the North End, past John Hancock’s counting house where nervous redcoats fumbled musket balls. Along the way, you’ll hear how Hancock beat smuggling charges, and discover why Puritans refused to name their horses.

Brawlers, Smugglers and Redcoats: Boston Self-Guided Walking Tour

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

Are you looking for a way to unlock the story behind Boston's beginnings without joining a tour group? Explore at your own pace with this affordable walking tour. • Hear the genesis of a nation on this highlight-packed tour from Copp’s Hill Burying Ground to the George Washington Monument • Listen to producer Gregg Squeglia, a local history fanatic and officer in the US Army Reserve • Do it all in 90 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 VoiceMap app and enter your code. The app displays directions to the starting point, and when you’re in the right place, just [pop in your headphones and] tap start. VoiceMap has automatic GPS playback, with turn-by-turn directions. It also works offline.

Boston's History and Highlights: A Self-Guided Audio Tour

1 hour 30 minutes to 2 hours

Dive into New England history with this tour combo of Salem and the Boston Freedom Trail. In Salem, uncover the truth behind the Witch Trials. Relive the panic which seized this colonial town. Learn about the victims and why they were accused. Explore this historic town, admire its preserved architecture, and unearth all its dark secrets. Then, walk in the footsteps of the Founding Fathers on Boston’s Freedom Trail. History comes alive with this gripping retelling of the fight for independence! After booking, check your email/text to download the separate Audio Tour Guide App by Action while connected to WiFi or mobile data. Enter the password, download the tour, and enjoy it offline. Follow the audio instructions and route from the designated starting point. New, Lifetime access, no expiry. Use it anytime, on any trip, as many times as you want. This isn't an entrance ticket. Check opening hours before your visit.

Freedom Trail and Salem Witch Trials App-Guided Audio Tour

2 to 4 hoursFree Cancellation

On this self-guided walking tour, you’ll explore the months of tension between the British and American colonists that culminated in the bloody shooting, now known as the Boston Massacre. “The riot on King Street” is what newspapers originally called the moment when British soldiers opened fire on an angry crowd in Boston on March 5, 1770. Embark on a historical journey, exploring events leading to March 5th and the impact of British impositions like the Vagrancy, Quartering, and Tax acts. Stand on State Street, the site of the Boston Massacre, and hear history's whispered tale. Learn of Ebenezer Richardson's role in igniting tensions, and pay homage at the Granary Burying Ground, where Saml Adams rests. Marvel at Long Wharf, witness to Boston's occupation, and savor culinary delights at Quincy Market. Each step unveils a narrative of resilience, bringing Boston's history vividly to life.

The Boston Massacre: An Audio Guide to the City’s Bloodiest Event

Boston's Freedom Trail: A Revolutionary Walking Tour

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Top Attractions in Boston

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Attractions

What are people saying about Boston

Regina_A, Sep 2026

Highly recommended!

It’s quite a bit of walking without a break but there’s so much history to cover in Boston. Our guide Julie (Jules) was amazing. She is so knowledgeable and told us all the interesting things while keeping us moving. So enjoyable. It was great! Loved it!!

Lexington & Concord 250th Birthday Tour with Concord Museum Entry

jack_a, Sep 2026

Talk about fantastic guides. Coach was the best.

YOU MUST GET COACH FOR YOUR TOUR GUIDE. He was excellent. The whole reason why I am giving this a 5 rating. He did not stop once in his sharing of knowledge and sharing his charming humor with you. He is now my measurement of the best guide I have ever had.

Freedom Trail Walking Tour with Bunker Hill and USS Constitution

Carol_L, Sep 2026

Awesome experience- highly recommend

100% wonderful experience with Mark! There is a reason for all the 5.0 reviews out there!! If you are looking for a cheesy, loud, perhaps costumed guide, Mark isn’t for you. If you are looking for a passionate, highly knowledgeable, mature professional guide, Mark IS the one!

Boston: Underground Railroad History Tour of Beacon Hill

Ernestine_N, Sep 2026

Preserved History

If you are interested in African American history in Boston this is the tour. Mehgan did an excellent job and was knowledgeable on the history of AA in Boston. She was very passionate in her tone on the free slaves and their struggles to become free as all humans back in the era. She gave breaks when walking the Beacon Hills area. We enjoyed our private tour due to another group canceled. Lucky for us :-). I would definitely recommend this tour with Mehgan. You will learn alot and be proud of AA history. I'm glad to know that Boston preserved it for generations. Kudos to Boston!!!

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

Reagan_H, Aug 2026

Best Boating Experience in Boston & Worth Every Penny!

My wife and I took my parents on this sail boat ride while they were in town, and this is now going to be a MUST-DO activity anytime we have any friends or family coming into town. As worried as we were about the evening being a bit overcast, this was such a great experience! The crew (Captain Jasper, Jessica, and Lauren) were genuinely wonderful, and they made us feel right at home on the boat. With smooth sailing and no loud engines, we had two nice hours of just enjoying the views and time with our family. Also, no one on our boat seemed to get sea sick so additional kudos to the crew for the smooth ride! Can’t wait to go back soon!!

Boston's Food and History: North End, Freedom Trail, Beacon Hill

C_D, Aug 2026

Very enjoyable yummy tour!

We had the pleasure of taking the Boston Food & History Tour with Nabil, and it was such a wonderful experience! Nabil was incredibly accommodating, friendly, and very knowledgeable about Boston’s history and food culture. We had a little trouble locating the starting point because the street sign had a different name than what appeared on my map. However, if you find the Registry of Motor Vehicles, you’re in the right place! We started at a very interesting bread company, where we got to try some delicious breads and learn about the history of this unique bakery and its bread-making traditions. From there, we stopped at a local grocery & deli, Salumeria, for a sandwich. We made our way to a pizza shop, Galleria Umberto, for a slice of cheese pizza. The pizza was delicious and had such a nostalgic, old-fashioned feel to it. The day we went was extremely hot, but Nabil was very thoughtful and made sure to bring us to shaded areas whenever possible, which we really appreciated. Our last stop was at a wonderful coffee house and pastry shop, Lavazza, where we enjoyed a cappuccino and a cannoli. Both were very good and were the perfect way to finish the tour. Along the way, we visited many historical sites and learned so much about Boston’s history. Nabil did a great job bringing everything to life while making the tour fun and enjoyable. Five hours may seem like a really long tour, the time flies & it does not seem too long. It is perfect! I would definitely recommend this tour to anyone looking for a great combination of delicious food, fascinating history, and a knowledgeable guide. We had a fantastic time and would absolutely recommend Nabil and this tour!

Walk the Historic Freedom Trail with Costumed Guide

Carrie_F, Jul 2026

Freedom tour with kids

I would highly recommend this tour! Our guide was very knowledgeable and a history teacher who was very good at keeping our kids (9&13) engaged. He kept a good pace and stopped frequently in shady spots. He lots of interesting details but drone on like some of the other guides we encountered. The 90 minute tour with 11 stops was really a perfect length for us, but if you wanted to see the other 5 sites, the guide gave advice on how to get to those on your own. If you are looking for a shorter version to do with your kids, I recommend this one!

Boston Walking Tour of The Freedom Trail, Small Group

Heather_D, Jul 2026

Amazing Insighful Thougt provoking

He was the consummate professional. His breadth of knowledge was not amazing but insightful. He explained so much that we didn't know including the impact of the native Americans and indigenous peoples on the United States He is the best tour guide in Boston Many stopped to take pictures with him in his period attire.

Historic Boston Hop-On Hop-Off Narrated Trolley Tour

Madison_R, Jul 2026

Really enjoyed the hop-on...

Really enjoyed the hop-on and hop-off trolley rides from all of the drivers! All of them were funny and very entertaining throughout the tours. We also really enjoyed this trolley ride options as a way to get to the major landmarks in Boston without having the walk, uber, or bike to destinations for 2 days!

Lexington, Massachusetts - Liberty Ride Trolley Tour

Daryl_E, Jun 2026

It was very well...

It was very well organised, the staff were extremely friendly and the tour guide was very informative. I highly recommend anyone who wishes to learn about the Revolutionary War that created the USA to check it out. Lexington is a beutiful picture perfect town and I was made very welcome. Top marks 10/10

A Taste of the Freedom Trail: Boston's Iconic Food History Tour

Kathryn_D, Oct 2025

Highly recommend this tour

Great tour with fun history, a lot of food and a nice amount of walking around the city. Katie (#102, apparently 2 Katies work for this company) was friendly, knowledgeable and a great guide. She made everyone feel comfortable and provided a lot of fun history facts about the city as well as its food but was not overpowering. The food was great and there was a lot of it. You definitely do not need a meal after this tour and it is coordinated to almost start with an appetizer, the beans and brown bread and end with dessert. The boston cream pie. All of the food was very good and each stop came with history about the food at that location. Katie also mentioned the history of some other restaurants that we didn’t stop at. There is an option to add two beers to your tour ticket and they space it out well. The beers are at stop one and three. There are 4 food stops on this tour. I have done food tours in many cities and this one ranks as one of the best. I will definitely be trying more of their tours.