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Top Boston Walking Tours

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Boston Tours

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Harvard University Campus Guided Walking Tour

What better way to see Harvard than through the eyes of a student? Join us for an unforgettable 75-minute student-led walking tour of Harvard University, …More

Likely to Sell Out
Likely to Sell Out
4.8 (3,654)

Harvard University Campus Guided Walking Tour

What better way to see Harvard than through the eyes of a student? Join us for an unforgettable 75-minute student-led walking tour of Harvard University,...

1 hour 10 minutes • Free Cancellation
4.8 (3,654)
from
$23
Boston Pizza Lovers Food and History Walking Tour

Feed BIG appetites, at small prices! A true Pizza Lover never settles for just samples. Enjoy three different FULL SIZE slices during this fun and …More

Likely to Sell Out
Likely to Sell Out
4.8 (1,101)

Boston Pizza Lovers Food and History Walking Tour

Feed BIG appetites, at small prices! A true Pizza Lover never settles for just samples. Enjoy three different FULL SIZE slices during this fun and...

2 hours 30 minutes • Free Cancellation
4.8 (1,101)
from
$59
Boston: Freedom Trail History Small Group Walking Tour

Boston's principal role in launching the American Revolution is linked by the brick-lined Freedom Trail. This world-famous pedestrian path is best experienced on foot, in …More

Likely to Sell Out
Likely to Sell Out
4.9 (7,915)

Boston: Freedom Trail History Small Group Walking Tour

Boston's principal role in launching the American Revolution is linked by the brick-lined Freedom Trail. This world-famous pedestrian path is best experienced on foot, in...

2 hours 30 minutes • Free Cancellation
4.9 (7,915)
from
$39
Boston Freedom Trail Walking Tour with Costumed Guide

The Tour of The Freedom Trail by the Histrionic Academy is the best way to see and learn about Boston's inspiring history. Following the Freedom …More

4.7 (2,712)

Boston Freedom Trail Walking Tour with Costumed Guide

The Tour of The Freedom Trail by the Histrionic Academy is the best way to see and learn about Boston's inspiring history. Following the Freedom...

1 hour 45 minutes • Free Cancellation
4.7 (2,712)
from
$26
Tour of Historic Fenway Park, America's Most Beloved Ballpark

Visit the most historic and oldest ballpark in MLB. Fenway Park, also known as "America's Most Beloved Ballpark" is uniquely nestled in the city of …More

Likely to Sell Out
Likely to Sell Out
4.8 (3,253)

Tour of Historic Fenway Park, America's Most Beloved Ballpark

Visit the most historic and oldest ballpark in MLB. Fenway Park, also known as "America's Most Beloved Ballpark" is uniquely nestled in the city of...

1 hour • Free Cancellation
4.8 (3,253)
from
$45
The Full Revolutionary Story Epic Small-Group Boston Walking Tour

This tour goes beyond surface‑level sightseeing and weaves the sites, people, and turning points of Boston’s iconic Freedom Trail into one immersive, chronological journey. Rather …More

Likely to Sell Out
Likely to Sell Out
5.0 (2,873)

The Full Revolutionary Story Epic Small-Group Boston Walking Tour

This tour goes beyond surface‑level sightseeing and weaves the sites, people, and turning points of Boston’s iconic Freedom Trail into one immersive, chronological journey. Rather...

3 hours • Free Cancellation
5.0 (2,873)
from
$59
Boston’s Politically Incorrect North End Food Tour

As the title suggests, Boston’s “Politically Incorrect “ Food Tour isn’t going to be your typical food tour. With his no BS style, your tour …More

Likely to Sell Out
Likely to Sell Out
4.8 (750)

Boston’s Politically Incorrect North End Food Tour

As the title suggests, Boston’s “Politically Incorrect “ Food Tour isn’t going to be your typical food tour. With his no BS style, your tour...

3 hours • Free Cancellation
4.8 (750)
from
$99
Boston’s North End Food Tour: Italian Flavors and Heritage Walk

This Boston food tour goes beyond the tourist trail—discover hidden gems, learn fascinating stories, and experience why the North End is the heart of Boston’s …More

4.9 (1,655)

Boston’s North End Food Tour: Italian Flavors and Heritage Walk

This Boston food tour goes beyond the tourist trail—discover hidden gems, learn fascinating stories, and experience why the North End is the heart of Boston’s...

2 hours • Free Cancellation
4.9 (1,655)
from
$66
Haunted Boston Booze and Boos Ghost Walking Tour

Unearth the spooky history of Boston on this 2.5-hour guided ghost tour and pub crawl. A costumed guide will lead you through historic streets and …More

4.7 (162)

Haunted Boston Booze and Boos Ghost Walking Tour

Unearth the spooky history of Boston on this 2.5-hour guided ghost tour and pub crawl. A costumed guide will lead you through historic streets and...

2 hours 30 minutes • Free Cancellation
4.7 (162)
from
$36
Boston Sweet Treats Food Tour: Fresh Donuts, Cider & Much More

Recently voted as one of Cool Destinations's top food tours in the US. Explore Boston’s sweetest side on the Underground Donut Tour, a delicious journey …More

Likely to Sell Out
Likely to Sell Out
4.9 (1,393)

Boston Sweet Treats Food Tour: Fresh Donuts, Cider & Much More

Recently voted as one of Cool Destinations's top food tours in the US. Explore Boston’s sweetest side on the Underground Donut Tour, a delicious journey...

2 hours • Free Cancellation
4.9 (1,393)
from
$70
Boston Freedom Trail History Pub Crawl Small-Group Tour

The Independence Pub Crawl combines Boston’s revolutionary history with four iconic and unique pubs along the Freedom Trail. An expert local guide will share the …More

Likely to Sell Out
Likely to Sell Out
4.9 (1,063)

Boston Freedom Trail History Pub Crawl Small-Group Tour

The Independence Pub Crawl combines Boston’s revolutionary history with four iconic and unique pubs along the Freedom Trail. An expert local guide will share the...

2 hours 15 minutes • Free Cancellation
4.9 (1,063)
from
$57
Boston's Freedom Trail and Charming Beacon Hill Tour

Go beyond the Freedom Trail and experience modern Boston through the city’s incredible history.  From the iconic Boston Harbor, to the famous Freedom Trail, into …More

4.9 (663)

Boston's Freedom Trail and Charming Beacon Hill Tour

Go beyond the Freedom Trail and experience modern Boston through the city’s incredible history.  From the iconic Boston Harbor, to the famous Freedom Trail, into...

2 hours • Free Cancellation
4.9 (663)
from
$25
Boston North End Food Tour with Authentic Local Flavors & Dishes

Discover Boston’s famous North End, where Italian tradition meets New England seafood, on our Secret Food Tour. Over 3 delicious hours, our local guide will …More

Likely to Sell Out
Likely to Sell Out
4.8 (1,602)

Boston North End Food Tour with Authentic Local Flavors & Dishes

Discover Boston’s famous North End, where Italian tradition meets New England seafood, on our Secret Food Tour. Over 3 delicious hours, our local guide will...

2 to 3 hours • Free Cancellation
4.8 (1,602)
from
$86
Boston's Food and History: North End, Freedom Trail, Beacon Hill

Uncover Boston’s best-kept secrets on a walking tour that blends history, culture, and flavor. Wander through the iconic North End, tasting fresh bread, pastries, pizza, …More

4.9 (1,893)

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

Uncover Boston’s best-kept secrets on a walking tour that blends history, culture, and flavor. Wander through the iconic North End, tasting fresh bread, pastries, pizza,...

5 hours • Free Cancellation
4.9 (1,893)
from
$91
Boston's 250th Freedom Trail Tour

The Tour of The Freedom Trail by the Histrionic Academy is the best way to see Boston. Depending on your chosen timeslot, guests will either …More

Likely to Sell Out
Likely to Sell Out
4.7 (1,235)

Boston's 250th Freedom Trail Tour

The Tour of The Freedom Trail by the Histrionic Academy is the best way to see Boston. Depending on your chosen timeslot, guests will either...

1 hour 45 minutes • Free Cancellation
4.7 (1,235)
from
$26
Boston Seafood Tour: Behind the Scenes at the Historic Fish Pier

Explore Boston’s seafood scene on a small-group, behind-the-scenes tour of the historic Fish Pier, tasting sustainably sourced local favorites while discovering the stories behind America’s …More

Likely to Sell Out
Likely to Sell Out
4.9 (583)

Boston Seafood Tour: Behind the Scenes at the Historic Fish Pier

Explore Boston’s seafood scene on a small-group, behind-the-scenes tour of the historic Fish Pier, tasting sustainably sourced local favorites while discovering the stories behind America’s...

2 hours 30 minutes • Free Cancellation
4.9 (583)
from
$77
Freedom Trail Walking Tour with Bunker Hill and USS Constitution

Most tours of the Freedom Trail are partial tours, skipping sections to save time. This tours will take you from start to finish -- with …More

Likely to Sell Out
Likely to Sell Out
5.0 (875)

Freedom Trail Walking Tour with Bunker Hill and USS Constitution

Most tours of the Freedom Trail are partial tours, skipping sections to save time. This tours will take you from start to finish -- with...

4 hours • Free Cancellation
5.0 (875)
from
$79
Boston: Underground Railroad History Tour of Beacon Hill

Boston's role in the fight to end legalized slavery is linked by the Black Heritage Trail in historic Beacon Hill. This pedestrian path is best …More

5.0 (195)

Boston: Underground Railroad History Tour of Beacon Hill

Boston's role in the fight to end legalized slavery is linked by the Black Heritage Trail in historic Beacon Hill. This pedestrian path is best...

2 hours 30 minutes • Free Cancellation
5.0 (195)
from
$35
North End and Boston Market District Food Tour with Local Guide

Recognized by Yelp as Massachusetts #1 food tour in 2025! Locally owned by Boston native. Specialize in award-winning best eats, culinary education, and history. Part …More

4.9 (181)

North End and Boston Market District Food Tour with Local Guide

Recognized by Yelp as Massachusetts #1 food tour in 2025! Locally owned by Boston native. Specialize in award-winning best eats, culinary education, and history. Part...

3 hours 30 minutes • Free Cancellation
4.9 (181)
from
$125
Boston Architectural Landmarks & History Tour with Photo Tips

Explore Boston’s top 3 attractions on a small-group walking tour in just two hours. A longtime local guide shares insightful historical commentary of the famous …More

5.0 (111)

Boston Architectural Landmarks & History Tour with Photo Tips

Explore Boston’s top 3 attractions on a small-group walking tour in just two hours. A longtime local guide shares insightful historical commentary of the famous...

2 hours • Free Cancellation
5.0 (111)
from
$55

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
The American revolution from beginning to end!!
New York City
The Full Revolutionary Story Epic Small-Group Boston Walking Tour
790trisham, Sep 2026
The American revolution from beginning to end!!
Fabulous tour with Tyler who was engaging and incredibly knowledgeable -- we highly recommend this tour and this particular tour guide!
Read more
Freedom Trail tour
New York City
Boston: Freedom Trail History Small Group Walking Tour
V1734ALdawng, Sep 2026
Freedom Trail tour
We had Jeremiah Poope as our guide. He was fantastic. He was informative, funny and very knowledgeable.. I would highly recommend this tour.
Read more
Highly interesting, engaging, and fun.
New York City
The Full Revolutionary Story Epic Small-Group Boston Walking Tour
Y5955BSryanm, Sep 2026
Highly interesting, engaging, and fun.
Tyler absolutely killed it as a tour guide. This guys interest in the history of Boston was palatable, his stories interesting and the views were bar none.As a guy doing my first solo trip, in Boston of all places, Tyler made it fun, interesting, and totally worth my time. He knew the crowd, planned for the windy weather, and somehow kept an eye on the traffic!Highly recommend the tour and as someone from Chicago that is familiar with a lot of tour guides, I’d totally recommend this guy as a guide for any of my friends or family visiting in the future. Can’t recommend enough.
Read more
Informative
New York City
Boston: Freedom Trail History Small Group Walking Tour
Judy_O, Sep 2026
Informative
Informative and historical! Our guide was so knowledgeable about Boston history, the walk was easy and fun.
Read more
Fun, Suprisingly Educational, & Delish!
New York City
Boston Sweet Treats Food Tour: Fresh Donuts, Cider & Much More
Taosbo, Sep 2026
Fun, Suprisingly Educational, & Delish!
Stephanie was our tour guide & she was fabulous! Every donut we tried was delicious, & they were all so different from each other. We not only learned about donuts, but also learned quite a bit of Boston history. The pace, length, & distance of the tour was just right, & we enjoyed every minute of it. Stephanie also answered our questions about other places, & was very helpful. We were looking for an Italian restaurant, & she gave us a few places to try, & when pressed, told us her fave. We just tried that one tonight, & the food, service, & ambience were all fantastic! Highly recommend this tour & our guide.
Read more
A special and delicious...
New York City
Boston’s North End Food Tour: Italian Flavors and Heritage Walk
Natalie_M, Sep 2026
A special and delicious...
A special and delicious food tour seasoned with history and culture. I do recommend this tour. Claire was a great guide!
Read more
A delicious history lesson
New York City
Boston Sweet Treats Food Tour: Fresh Donuts, Cider & Much More
megmP4929IN, Sep 2026
A delicious history lesson
Great donuts, fun side quests and excellent history lesson! 10/10! Second Underground Donut Tour and this tour solidified I’ll always search for this company when traveling!
Read more
Fun Food and History Tour
New York City
Boston’s Food and History: North End, Freedom Trail, Beacon Hill
W6848GKkathyr, Sep 2026
Fun Food and History Tour
Great, Good Food, Knowledge Guide, small group . Fun Time
Read more
Hahvahd Tour Review
New York City
Harvard University Campus Guided Walking Tour
mur3545, Sep 2026
Hahvahd Tour Review
Our tour of Harvard was excellent. A real historical view of the University coupled with an interesting reflection of the students and its/their accomplishments. First rate!
Read more
Enjoyable learning opportunity
New York City
Boston Freedom Trail Walking Tour with Costumed Guide
cheryldY8720JU, Sep 2026
Enjoyable learning opportunity
John Hancock taught us a lot on this tour. I enjoyed hearing the stories that you don't learn about in school. I understand more about the important events that shaped our country plus interesting color commentary that kept our attention.
Read more
So much fun!
New York City
Boston’s North End Food Tour: Italian Flavors and Heritage Walk
jamieeK7044CZ, Sep 2026
So much fun!
Lexie was great! So much knowledge and passion for the area! We tried so much food and she was organized, funny, and entertaining! Highly recommend!
Read more
Awesome tour!
New York City
Boston’s Politically Incorrect North End Food Tour
Kim_S, Sep 2026
Awesome tour!
Anthony wasgreat. Tons of delicious food! Funny and down to earth! I suggest bring a couple of ziplocks! So you are not stuffed by the end! Great experience!
Read more
Interesting Tour with Fantastic Guide
New York City
Boston North End Food Tour with Authentic Local Flavors & Dishes
Howard_J, Sep 2026
Interesting Tour with Fantastic Guide
We have been on many food tours in many cities and this was one of the best thanks to Elizabeth. She was not only well versed in the dishes we tried but brought a significant amount of knowledge about the history of the North End which made the tour that much more interesting. I would highly recommend this tour and suggest you request Elizabeth as your guide.
Read more
Highly recommend
New York City
Boston Freedom Trail Walking Tour with Costumed Guide
Dawn_G, Sep 2026
Highly recommend
Very interesting and informative. Guide was very knowledgeable and fun. Good value for money. Highly recommend
Read more
Fenway field tour
New York City
Tour of Historic Fenway Park, America’s Most Beloved Ballpark
Expedition642649, Sep 2026
Fenway field tour
We had an excellent tour guide and was very interesting. A great tour .
Read more
A Different Boston
New York City
Boston Seafood Tour: Behind the Scenes at the Historic Fish Pier
Kenneth_S, Sep 2026
A Different Boston
Very interesting and very different view of Boston. The food on the tour was all great local specialties. Nabil did a fabulous job.
Read more
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