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Top Massachusetts Architecture Tours

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Massachusetts Tours

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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

Boston, USA
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 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

Boston, USA
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
Downtown Freedom Trail, Beacon Hill & Back Bay Walking Tour

See THREE AREAS on our Walking Tour: The Freedom Trail Downtown, Beacon Hill and Back Bay! No Costumes! No Huge Groups! Enjoy Boston's history, vibrant …More

Boston, USA
4.7 (459)

Downtown Freedom Trail, Beacon Hill & Back Bay Walking Tour

See THREE AREAS on our Walking Tour: The Freedom Trail Downtown, Beacon Hill and Back Bay! No Costumes! No Huge Groups! Enjoy Boston's history, vibrant...

2 hours • Free Cancellation
4.7 (459)
from
$45
Downtown Freedom Trail Walking Tour - History & Architecture

No Costumes! No Yelling! No Huge Tour Group! Just the best in learning about Boston. Experience the history, architecture and culture of Boston wrapped in …More

Boston, USA
4.6 (187)

Downtown Freedom Trail Walking Tour - History & Architecture

No Costumes! No Yelling! No Huge Tour Group! Just the best in learning about Boston. Experience the history, architecture and culture of Boston wrapped in...

1 hour 10 minutes • Free Cancellation
4.6 (187)
from
$30
Boston Architecture Cruise of Charles River & Boston Harbor

Experience the best of Boston and Cambridge from the water on this premier 2-hour architecture cruise. Hosted by the Charles River Boat Company, this tour …More

Cambridge, USA
4.6 (22)

Boston Architecture Cruise of Charles River & Boston Harbor

Experience the best of Boston and Cambridge from the water on this premier 2-hour architecture cruise. Hosted by the Charles River Boat Company, this tour...

2 hours • Free Cancellation
4.6 (22)
from
$49
Boston Freedom Trail Walking Tour | Small Group

Explore Boston on a small-group walking tour along the iconic Freedom Trail, where the events leading up to the American Revolution come to life through …More

Boston, USA
4.6 (98)

Boston Freedom Trail Walking Tour | Small Group

Explore Boston on a small-group walking tour along the iconic Freedom Trail, where the events leading up to the American Revolution come to life through...

1 hour 30 minutes • Free Cancellation
4.6 (98)
from
$45
Boch Center Wang Theatre Behind the Scenes Tour

Visit the historic Boch Center Wang Theatre and take a 1-hour behind-the-scenes tour of one of Boston’s most prominent theatrical landmarks - plus get an …More

Likely to Sell Out
Likely to Sell Out
Boston, USA
4.9 (101)

Boch Center Wang Theatre Behind the Scenes Tour

Visit the historic Boch Center Wang Theatre and take a 1-hour behind-the-scenes tour of one of Boston’s most prominent theatrical landmarks - plus get an...

1 hour 15 minutes • Free Cancellation
4.9 (101)
from
$25
Beacon Hill Boston Walking Tour: History + Fun Photo Tips

Explore Beacon Hill on a small-group walking tour led by a longtime Boston guide. Walk along brick sidewalks while listening to insightful commentary with insider …More

Boston, USA
4.9 (171)

Beacon Hill Boston Walking Tour: History + Fun Photo Tips

Explore Beacon Hill on a small-group walking tour led by a longtime Boston guide. Walk along brick sidewalks while listening to insightful commentary with insider...

1 hour 30 minutes • Free Cancellation
4.9 (171)
from
$45
Nantucket Self-Guided Audio Walking Tour: Beyond the Cobblestones

Explore historic downtown Nantucket on a self-guided audio walking tour. Follow a roughly 2-mile route as stories and directions play automatically along the way. Hear …More

Nantucket, USA
4.2 (11)

Nantucket Self-Guided Audio Walking Tour: Beyond the Cobblestones

Explore historic downtown Nantucket on a self-guided audio walking tour. Follow a roughly 2-mile route as stories and directions play automatically along the way. Hear...

2 to 3 hours • Free Cancellation
4.2 (11)
from
$10
Martha’s Vineyard Self-Guided Driving & Walking Audio Tour

Get ready to visit one of the greatest vacation spots in the USA, a favorite among celebrities and even presidents! Martha’s Vineyard is home to …More

Martha's Vineyard, USA
4.0 (10)

Martha’s Vineyard Self-Guided Driving & Walking Audio Tour

Get ready to visit one of the greatest vacation spots in the USA, a favorite among celebrities and even presidents! Martha’s Vineyard is home to...

2 to 3 hours • Free Cancellation
4.0 (10)
from
$15
Beacon Hill + Back Bay Walking Tour: History + Fun Photo Tips

Explore three of Boston’s most scenic attractions on a small-group walking tour in just two hours. A longtime local guide shares insightful historical commentary and …More

Boston, USA
5.0 (75)

Beacon Hill + Back Bay Walking Tour: History + Fun Photo Tips

Explore three of Boston’s most scenic attractions on a small-group walking tour in just two hours. A longtime local guide shares insightful historical commentary and...

2 hours • Free Cancellation
5.0 (75)
from
$55
Guided Walking Tour of Copley Square to Downtown Boston Freedom Trail

Enjoy the vibrant atmosphere of Boston on this guided, 2-hour walking tour. Includes the History, Architecture and Culture of Boston. See the Victorian brownstone homes …More

Likely to Sell Out
Likely to Sell Out
Boston, USA
4.5 (45)

Guided Walking Tour of Copley Square to Downtown Boston Freedom Trail

Enjoy the vibrant atmosphere of Boston on this guided, 2-hour walking tour. Includes the History, Architecture and Culture of Boston. See the Victorian brownstone homes...

2 hours • Free Cancellation
4.5 (45)
from
$45
Salem Movie Magic Tour: Hocus Pocus and Bewitched locations

We begin our tour at the restaurant Tipsy Cowboy. We will watch clips from Hocus Pocus, the Bewitched episode in Salem, and Hubie Halloween while …More

Salem, USA
4.8 (34)

Salem Movie Magic Tour: Hocus Pocus and Bewitched locations

We begin our tour at the restaurant Tipsy Cowboy. We will watch clips from Hocus Pocus, the Bewitched episode in Salem, and Hubie Halloween while...

2 hours • Free Cancellation
4.8 (34)
from
$43
North End-Little Italy Boston Walking Tour: History + Photo Tips

Explore Boston’s North End–Little Italy on a small-group walking tour led by a longtime local guide. Walk through the city’s oldest neighborhood and learn about …More

Boston, USA
5.0 (28)

North End-Little Italy Boston Walking Tour: History + Photo Tips

Explore Boston’s North End–Little Italy on a small-group walking tour led by a longtime local guide. Walk through the city’s oldest neighborhood and learn about...

1 hour 30 minutes • Free Cancellation
5.0 (28)
from
$45
Salem Merchants and Mansions Guided Architecture Walking Tour

All ages Spring/summer only Merchants & Mansions Architecture Tour Salem has one of the most naturally varied collections of historic structures in the country, spanning …More

Salem, USA
5.0 (21)

Salem Merchants and Mansions Guided Architecture Walking Tour

All ages Spring/summer only Merchants & Mansions Architecture Tour Salem has one of the most naturally varied collections of historic structures in the country, spanning...

90 to 120 minutes • Free Cancellation
5.0 (21)
from
$36
Discovering Oak Bluffs: A Self-Guided Audio Tour

Discover how a small religious summer camp transformed into one of Martha’s Vineyard’s most popular island destinations on this walking tour through the town of …More

Martha's Vineyard, USA

Discovering Oak Bluffs: A Self-Guided Audio Tour

Discover how a small religious summer camp transformed into one of Martha’s Vineyard’s most popular island destinations on this walking tour through the town of...

75 to 90 minutes • Free Cancellation
from
$12
Guided Tour of Crane Estate All-Inclusive Day Trip from Boston

Step into the grandeur of New England’s past with a visit to Castle Hill on the Crane Estate, a breathtaking National Historic Landmark overlooking the …More

5.0 (3)

Guided Tour of Crane Estate All-Inclusive Day Trip from Boston

Step into the grandeur of New England’s past with a visit to Castle Hill on the Crane Estate, a breathtaking National Historic Landmark overlooking the...

6 hours • Free Cancellation
5.0 (3)
from
$95
North End Boston Mafia Exploration Game and Tour

Discover Boston’s Mafia past by solving challenges and unlocking stories on your phone, leading you to new places and amazing stories. Play our engaging exploration …More

Boston, USA
4.3 (10)

North End Boston Mafia Exploration Game and Tour

Discover Boston’s Mafia past by solving challenges and unlocking stories on your phone, leading you to new places and amazing stories. Play our engaging exploration...

130 to 160 minutes • Free Cancellation
4.3 (10)
from
$6
Boston Civil War and Abolition Movement: A Self-Guided Audio Tour

Are you looking for a way to discover Boston without joining a tour group? Explore at your own pace with this self-guided walking tour. • …More

Boston, USA
5.0 (2)

Boston Civil War and Abolition Movement: A Self-Guided Audio Tour

Are you looking for a way to discover Boston without joining a tour group? Explore at your own pace with this self-guided walking tour. •...

90 to 120 minutes
5.0 (2)
from
$12
Walk the Freedom Trail with a Local Tour Guide

The Freedom Trail is Boston's historic backbone, guiding you through key sites that shaped American history. This 2-hour walking tour offers an engaging exploration of …More

Boston, USA
5.0 (1)

Walk the Freedom Trail with a Local Tour Guide

The Freedom Trail is Boston's historic backbone, guiding you through key sites that shaped American history. This 2-hour walking tour offers an engaging exploration of...

2 hours • Free Cancellation
5.0 (1)
from
$39

Frequently Asked Questions

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

Recent tour reviews
Castle Hill Crane Estate
New York City
Guided Tour of Crane Estate All-Inclusive Day Trip from Boston
nancycT9190IN, Sep 2026
Castle Hill Crane Estate
The trip to Castle Hill Cranes Estate was worthwhile. Keolis provided excellent communication prior and during the trip - when the pick up was going to be a bit late, there was an immediate text. Keolis made it a seamless trip!
Read more
Saba is an excellent...
New York City
Beacon Hill Boston Walking Tour: History + Fun Photo Tips
Allie_B, Sep 2026
Saba is an excellent...
Saba is an excellent guide through Beacon Hill! This is my second time booking this tour and she does not disappoint. She has a lot of knowledge and passion about the area. She has a very creative lenses and has great recommendations for taking awesome photos! She is sure to capture meaningful moments of you along the way as well! Highly recommend this experience!
Read more
Great cruise.
New York City
Boston Architecture Cruise of Charles River & Boston Harbor
597kurtisw, Sep 2026
Great cruise.
Peter was great & knowledgeable.
Read more
Saba was a delight! She...
New York City
Boston Architectural Landmarks & History Tour with Photo Tips
Linda_B, Sep 2026
Saba was a delight! She...
Saba was a delight! She was very knowledgeable of the architecture in the Back Bay and Beacon Hill areas. She also gave great photo tips, along with transportation, lunch and shopping suggestions. I would highly recommend the tour. Enjoy!
Read more
Fabulous experience
New York City
Boston’s Freedom Trail and Charming Beacon Hill Tour
J999PYtc, Sep 2026
Fabulous experience
Our tour guide Olivia was exceptional - her knowledge, enthusiasm, passion and professionalism. We really enjoyed our time on the tour with her, thanks Olivia x
Read more
Boston pics
New York City
Boston Architectural Landmarks & History Tour with Photo Tips
Thomas_R, Sep 2026
Boston pics
A beautiful day and well organized tour by Saba! She shared great information and super fantastic photo spots! A treasure of memories was created.
Read more
Bob is great
New York City
Boston’s Freedom Trail and Charming Beacon Hill Tour
Explorer11290625789, Sep 2026
Bob is great
Loved Bob’s enthusiasm and knowledge of Boston! Super detailed and dedicated to teaching things, even to locals
Read more
The charming morning in Beacon Hill
New York City
Beacon Hill + Back Bay Walking Tour: History + Fun Photo Tips
gailpZ5161UC, Sep 2026
The charming morning in Beacon Hill
The guide is extremely knowledgeable and has amazing stories about Beacon Hill. She’s very accommodating and verb time flies by.
Read more
Don't miss this unique opportunity!
New York City
Boston Architecture Cruise of Charles River & Boston Harbor
bharrin3940, Sep 2026
Don't miss this unique opportunity!
We took the 9:30 am architectural tour today, Saturday, September 12 and it was fantastic. My daughters purchased the tickets for my husband's birthday so I can't speak to the price, but we all enjoyed seeing the city from a different perspective.....the water. Our tour guide was extremely knowledgeable about the buildings that he highlighted. He spoke about the type of architecture, the architect who designed it and shared interesting tidbits about each. It didn't hurt that the weather was absolutely beautiful so we were very comfortable as well. We have lived near Boston all of our lives, and have taken several different harbor cruises, but this was by far, the best.
Read more
Great small group tour
New York City
Beacon Hill + Back Bay Walking Tour: History + Fun Photo Tips
Sharon K, Sep 2026
Great small group tour
Great small group tour. Guide very knowledgeable about history of the area and gave tidbits bits on certain houses regarding* history. She took several pictures of our group
Read more
Walking tour
New York City
Walk the Freedom Trail with a Local Tour Guide
Lindal_t, Sep 2026
Walking tour
Very knowledgeable! A lot of standing in one place. Very busy holiday weekend, lots of tours in the same area.
Read more
Take this tour!
New York City
Salem Merchants and Mansions Guided Architecture Walking Tour
W4121TVamandab, Sep 2026
Take this tour!
Sean was an absolute powerhouse of information and delight! The tour was incredibly informative, taking us all over downtown Salem and helping us understand the history through the lens of architectural changes. I highly recommend the tour. Thanks Sean!
Read more
Well Worth The Money!
New York City
Martha’s Vineyard Self-Guided Driving & Walking Audio Tour
Tammy_B, Sep 2026
Well Worth The Money!
I enjoyed this tour! This is the second time I purchased it; the first time was very confusing but this time it was great!
Read more
So enjoyable! Highly recommend!
New York City
Beacon Hill Boston Walking Tour: History + Fun Photo Tips
Z2399RMdianes, Aug 2026
So enjoyable! Highly recommend!
I booked this tour as a morning anniversary gift for my husband and my 35th anniversary as we were spending 5 days in Boston last week to attend evening concerts that were part of a music workshop in which our daughter was participating. There were 4 of us in the tour group along with our guide, Saba. Saba was so pleasant, knowledgeable, accommodating, informative, and friendly. We learned a lot about Beacon Hill - both history and current day. Saba gave us some good photo tips, AND she took some fantastic photos of us - individually and as couples - along the way. All in all, this was an enjoyable, relaxing, illuminating adventure. Thank you, Saba! I hope our paths cross again.
Read more
Informative Tour
New York City
Downtown Freedom Trail, Beacon Hill & Back Bay Walking Tour
Sandra_L, Aug 2026
Informative Tour
This turned out being a private tour for us which was a bonus. Allen answered all of our questions and took his time . The Freedom Trail component was informative and thorough. It was nice to include Beacon Hill to see the homes and learn who lived there. Boston Common and Public Gardens were included as well. History of Back Bay was remarkable.
Read more
Glimpse into guilded age
New York City
Guided Tour of Crane Estate All-Inclusive Day Trip from Boston
teresafE5403VB, Aug 2026
Glimpse into guilded age
Clam Box great add-in. Best for those ready to walk & enjoy ocean views.
Read more
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