Cool Destinations
Top Boston activities
Top Boston landmarks
Beyond Boston
Boston trip ideas
  • Tours by category
  • Tours by accessibility
  • Tours by feature
  • Tours by the numbers
  • Top Boston landmark tours
  • Tours in nearby places
  • Explore Massachusetts tours
  • Boston travel guides
  • Boston travel calendar
Language $Currency
Login / Sign up
Bookings
Bookings
Cool Rewards Rewards
$0.00
Cool Rewards Rewards
$0.00
Wishlists
Wishlists
Profile
Help Center
Language
Log out
Start your search
Change your search
Place or activity
Select Dates

Top Boston Private Sightseeing Tours

97 Results
Sort by:
Featured
Filter
Languages Clear
Time of Day Clear
95
61
43
Duration Clear
7
56
48
2
0
Price Clear
$0 $500+
Rating Clear
63
83
88
Specials Clear
80
22
0
97
7
Features Clear
50
11
81
1
86
31
Accessibility Clear
5
59
83
Families Clear
8
51
6

Boston Tours

Attractions

Guides

Calendar

Boston's Beacon Hill Underground Railroad Audio Walking Tour

Discover Beacon Hill's Underground Railroad history while walking its cobbled stones streets. On this historic adventure you'll see the old hidden alley's slave catchers once …More

4.7 (29)

Boston's Beacon Hill Underground Railroad Audio Walking Tour

Discover Beacon Hill's Underground Railroad history while walking its cobbled stones streets. On this historic adventure you'll see the old hidden alley's slave catchers once...

45 to 55 minutes • Free Cancellation
4.7 (29)
from
$10
Private 1.5-Hour Freedom Trail Walking Tour with Costumed Guide

A 90-minute walking tour of the Freedom Trail that covers the first 11 historic sites. It starts in Boston Common at the Visitor Information Center …More

4.8 (43)

Private 1.5-Hour Freedom Trail Walking Tour with Costumed Guide

A 90-minute walking tour of the Freedom Trail that covers the first 11 historic sites. It starts in Boston Common at the Visitor Information Center...

90 to 240 minutes • Free Cancellation
4.8 (43)
from
$450
Salem Full Day Private Tour from Boston

Enjoy a private pickup and ride to historic Salem with your guide. Walk the streets where hysteria once ruled, and learn about the Puritan past …More

Likely to Sell Out
Likely to Sell Out
5.0 (5)

Salem Full Day Private Tour from Boston

Enjoy a private pickup and ride to historic Salem with your guide. Walk the streets where hysteria once ruled, and learn about the Puritan past...

8 hours • Hotel pickup offered • Free Cancellation
5.0 (5)
from
$155
Cambridge, Lexington, & Concord: Private Revolutionary War Tour

Immerse yourself in this Revolutionary War full-day driving tour which will take you on a journey to explore the significant sites of the American Revolution. …More

5.0 (1)

Cambridge, Lexington, & Concord: Private Revolutionary War Tour

Immerse yourself in this Revolutionary War full-day driving tour which will take you on a journey to explore the significant sites of the American Revolution....

6 hours • Hotel pickup offered
5.0 (1)
from
$160
Boston Massachusetts Private Photography Tour

We are soulful photographers. Our objective is to create absolutely stunning photographs for you that you will cherish and proudly share with your friends and …More

5.0 (3)

Boston Massachusetts Private Photography Tour

We are soulful photographers. Our objective is to create absolutely stunning photographs for you that you will cherish and proudly share with your friends and...

1 hour • Free Cancellation
5.0 (3)
from
$130
Boston Freedom Trail Self-Guided Audio Tour

Walk in the footsteps of America’s revolutionaries with our immersive Boston Freedom Trail audio tour! Unlike crowded tours, this guide brings history to life at …More

5.0 (2)

Boston Freedom Trail Self-Guided Audio Tour

Walk in the footsteps of America’s revolutionaries with our immersive Boston Freedom Trail audio tour! Unlike crowded tours, this guide brings history to life at...

2 days • Free Cancellation
5.0 (2)
from
$9
Private Culinary Walking Tour in Boston Historic Districts

This private culinary walking tour introduces Boston’s historic districts through authentic regional flavors. You begin in the Blackstone Block where narrow streets reflect early commercial …More

5.0 (1)

Private Culinary Walking Tour in Boston Historic Districts

This private culinary walking tour introduces Boston’s historic districts through authentic regional flavors. You begin in the Blackstone Block where narrow streets reflect early commercial...

3 hours
5.0 (1)
from
$329
Boston Private City Tour

Discover Boston and Cambridge on a private six-hour sightseeing experience designed around your group’s interests. Travel in a comfortable private vehicle while your knowledgeable driver-guide …More

Likely to Sell Out
Likely to Sell Out
4.7 (66)

Boston Private City Tour

Discover Boston and Cambridge on a private six-hour sightseeing experience designed around your group’s interests. Travel in a comfortable private vehicle while your knowledgeable driver-guide...

6 hours • Hotel pickup offered • Free Cancellation
4.7 (66)
from
$925
Self Guided Classic Freedom Trail Location Aware (GPS) Walking Audio Tour

Discover Boston's Revolutionary history on this Classic Freedom Trail Walking Tour including Historic Downtown Boston, the North End and Charlestown. -Go anytime, at your own …More

4.4 (276)

Self Guided Classic Freedom Trail Location Aware (GPS) Walking Audio Tour

Discover Boston's Revolutionary history on this Classic Freedom Trail Walking Tour including Historic Downtown Boston, the North End and Charlestown. -Go anytime, at your own...

2 to 3 hours • Free Cancellation
4.4 (276)
from
$8
Boston Private 3-Hour Tour by Car

This private car tour is the perfect way to orientate yourself to Boston, to see not just the historic sites, but the entire city. On …More

Likely to Sell Out
Likely to Sell Out
5.0 (143)

Boston Private 3-Hour Tour by Car

This private car tour is the perfect way to orientate yourself to Boston, to see not just the historic sites, but the entire city. On...

3 hours • Hotel pickup offered • Free Cancellation
5.0 (143)
from
$550
Boston Freedom Trail Self-Guided Tour with Audio Narration & Map

Walk in the footsteps of Revolutionary War heroes with this self-guided audio tour of Boston’s Freedom Trail! Get the facts behind the story of Paul …More

4.6 (108)

Boston Freedom Trail Self-Guided Tour with Audio Narration & Map

Walk in the footsteps of Revolutionary War heroes with this self-guided audio tour of Boston’s Freedom Trail! Get the facts behind the story of Paul...

3 to 4 hours • Free Cancellation
4.6 (108)
from
$10
Boston Private Food Tour with 6+ Authentic Tastings

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
5.0 (176)

Boston Private Food Tour with 6+ Authentic Tastings

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...

3 hours
5.0 (176)
from
$160
Private City Tour of Boston and Cambridge

This private full-day tour will take you through every highlight Boston and Cambridge! The tour will include sights such as the Old North Church, Paul …More

5.0 (44)

Private City Tour of Boston and Cambridge

This private full-day tour will take you through every highlight Boston and Cambridge! The tour will include sights such as the Old North Church, Paul...

7 hours • Hotel pickup offered • Free Cancellation
5.0 (44)
from
$149
Highlights of Boston Private Tour

A full-day tour of Boston's history, culture, and food! Visit the historic North End and walk in the steps of Paul Revere. Stroll amongst the …More

Likely to Sell Out
Likely to Sell Out
4.9 (35)

Highlights of Boston Private Tour

A full-day tour of Boston's history, culture, and food! Visit the historic North End and walk in the steps of Paul Revere. Stroll amongst the...

5 hours 30 minutes • Hotel pickup offered • Free Cancellation
4.9 (35)
from
$135
Boston Sightseeing Tour - a fully-narrated driving tour

This tour will begin at your home, hotel or cruise ship and take you past the most interesting places in Boston including the Paul Revere …More

Likely to Sell Out
Likely to Sell Out
4.9 (63)

Boston Sightseeing Tour - a fully-narrated driving tour

This tour will begin at your home, hotel or cruise ship and take you past the most interesting places in Boston including the Paul Revere...

3 hours • Hotel pickup offered • Free Cancellation
4.9 (63)
from
$495
Private Day Trip to Lexington and Concord from Boston

Visit the real locations where the American Revolution began, while listening to hilarious yet little-known stories about our ancestors. Stand on Lexington Battle Green and …More

5.0 (35)

Private Day Trip to Lexington and Concord from Boston

Visit the real locations where the American Revolution began, while listening to hilarious yet little-known stories about our ancestors. Stand on Lexington Battle Green and...

6 hours 30 minutes • Hotel pickup offered • Free Cancellation
5.0 (35)
from
$149
Lexington and Concord 3 hour private car tour from Boston

This half day private car tour is a perfect way to visit the Revolutionary War towns of Lexington and Concord and see the site where …More

Likely to Sell Out
Likely to Sell Out
5.0 (40)

Lexington and Concord 3 hour private car tour from Boston

This half day private car tour is a perfect way to visit the Revolutionary War towns of Lexington and Concord and see the site where...

3 hours • Hotel pickup offered • Free Cancellation
5.0 (40)
from
$550
Private North End Neighborhood Tour

Yelp's 2025 pick for Massachusetts #1 food tour! Create food memories with one of Boston's original food tours. Our North End Neighborhood Tour offers a …More

Likely to Sell Out
Likely to Sell Out
5.0 (33)

Private North End Neighborhood Tour

Yelp's 2025 pick for Massachusetts #1 food tour! Create food memories with one of Boston's original food tours. Our North End Neighborhood Tour offers a...

3 hours 30 minutes • Free Cancellation
5.0 (33)
from
$135
Full-Day Minivan Tour of Revolutionary Boston, Lexington and Concord

Immerse yourself in our colonial history! On this six-hour driving tour, you will see the sights and hear the stories of Boston's colonial past narrated …More

Likely to Sell Out
Likely to Sell Out
5.0 (23)

Full-Day Minivan Tour of Revolutionary Boston, Lexington and Concord

Immerse yourself in our colonial history! On this six-hour driving tour, you will see the sights and hear the stories of Boston's colonial past narrated...

6 hours • Hotel pickup offered • Free Cancellation
5.0 (23)
from
$975
Private Day Tour of Salem and Boston

Whirlwind full-day tour of Boston and Salem! Drive to Salem to learn about the witch hunt hysteria of the late 17th century. Walk through historic …More

5.0 (30)

Private Day Tour of Salem and Boston

Whirlwind full-day tour of Boston and Salem! Drive to Salem to learn about the witch hunt hysteria of the late 17th century. Walk through historic...

7 hours 30 minutes • Hotel pickup offered • Free Cancellation
5.0 (30)
from
$143

Frequently Asked Questions

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

Recent tour reviews
Jenny, our guide was...
New York City
Private Day Trip to Lexington and Concord from Boston
Linda_H, Sep 2026
Jenny, our guide was...
Jenny, our guide was excellent. Her knowledge of all the facts and details helped bring the history alive.
Read more
Rainy day in Boston
New York City
Highlights of Boston Private Tour
measik, Sep 2026
Rainy day in Boston
We had a great day in Boston while waiting on our flight. Weather was not great but Mark made the best of it for us!! He was very knowledgeable and ready with an umbrella anytime we needed. Great coffee at cafe Victoria to start things off. Mark recommended the cannoli and did not steer us wrong with that. Such a fun way to kill time before a later flight and could not really say enough about Mark! He really gave us a great history lesson and lots of fun facts about the city. Can’t wait to come back and do the Salem tour with him
Read more
Joan was amazing!!! She...
New York City
Boston Private 3-Hour Tour by Car
Kimberly_S, Sep 2026
Joan was amazing!!! She...
Joan was amazing!!! She was a wealth of knowledge on both our Salem and Boston tours. She took her time and made sure we saw everything on our wish list. I would highly recommend her!!!
Read more
Christian, #1 tour guide
New York City
Boston Private 3-Hour Tour by Car
Rebecca_S, Sep 2026
Christian, #1 tour guide
If you want to see Boston with a 3-Hour Tour by car, I would recommend using this company. Our tour guide, Christian, was polite, considerate of our requests on the trip, and extremely knowledgable regarding all aspects of Boston history. Joan, handling our tour request, was fast getting back to me regarding tour time options and making arranging that insured our tour easy and enjoyable.
Read more
Learned so much!
New York City
Private Day Trip to Lexington and Concord from Boston
Teresaveltri624, Sep 2026
Learned so much!
Maria was an excellent guide. We learned so much. She tailored the trip to our wishes and gave us a day we will always remember.
Read more
Boston Tour
New York City
Boston Sightseeing Tour – a fully-narrated driving tour
Alan_M, Sep 2026
Boston Tour
Very knowable about history and events concerning Boston. Polite informative and pleasant narration during entire three hour tour. Well worth the price…..
Read more
Awesome tour
New York City
Boston Private Food Tour with 6+ Authentic Tastings
lisadT2614ZG, Sep 2026
Awesome tour
Elizabeth was super knowledgeable and so fun!
Read more
Great Freedom Trail tour!
New York City
Self Guided Classic Freedom Trail Location Aware (GPS) Walking Audio Tour
margotn994, Sep 2026
Great Freedom Trail tour!
This app was perfect for us. we walked the entirety of the Freedom Trail with it and it allowed for seamless stops, entertaining history and succinct presentations for first time Boston visitors. Thank you!
Read more
I loved the flexibility...
New York City
Self Guided Classic Freedom Trail Location Aware (GPS) Walking Audio Tour
Scott_S, Sep 2026
I loved the flexibility...
I loved the flexibility of this self-paced tour. It was also nice how the GPS feature of the tour app was able to track your location and coordinate the audio.
Read more
Informative and interesting.
New York City
Lexington and Concord 3 hour private car tour from Boston
Lavonna_D, Sep 2026
Informative and interesting.
Great tour! Our guide, Christian, was interesting and informative as he lead us back in time to the day the American Revolutionary War started in Lexington and Concord. As a retired history teacher he really knew what he was talking about. Interesting to listen to and follow. The 4 of us had a great day. The drive is beautiful too as you drive in the countryside of Lexington and Concord. I would highly recommend!
Read more
Freedom Trail
New York City
Boston Freedom Trail Self-Guided Tour with Audio Narration & Map
tallymom81, Sep 2026
Freedom Trail
Very informative and loved that you could take your time and explore. It was a little confusing going in and out if the old cemetery, but it was easy to get back on track.
Read more
5 stars
New York City
Private City Tour of Boston and Cambridge
ROBERT_F, Sep 2026
5 stars
Very informative it was all understanding of the area in the history of everything that was involved during the 17th and 18th century
Read more
Great tour!
New York City
Boston Freedom Trail Self-Guided Tour with Audio Narration & Map
Ellen_K, Sep 2026
Great tour!
The app was easy to use and the red brick trail was extremely helpful to follow through the city. Interesting historical information.
Read more
Great Day in Boston with BJ!
New York City
Private City Tour of Boston and Cambridge
Lindsay_B, Aug 2026
Great Day in Boston with BJ!
This tour definitely exceeded my expectations! We had 3 generations of travelers from ages 7-79 and everyone really enjoyed it. It was all of our our first time in Boston and this was a great activity for our first day. We had BJ as our guide and he communicated with me in advance of the tour and picked us up timely at our hotel. Our first stop was an Italian coffee/pastry shop in the North End. There we talked through a loose plan for the day, but the best thing about this tour was that BJ was totally flexible… There were certain places we wanted to spend more time, and BJ accommodated us, provided interesting commentary and even helping entertain the kids when one was bored and the rest of us were taking a little longer at a site/exhibit. His vehicle was clean, fully functioning and he had parking passes at certain key places allowing us to pack a lot into one day. I would definitely recommend this tour and BJ to anyone visiting Boston! We will talk about this day and the places we visited for years to come. Already want to plan a return trip! :)
Read more
Excellent tour
New York City
Boston Private Food Tour with 6+ Authentic Tastings
mellU4266VK, Aug 2026
Excellent tour
Jess is a superb and knowledgeable guide who really went the extra mile. We loved the tour.
Read more
Shaka is a Great Boston Guide
New York City
Boston Freedom Trail Self-Guided Audio Tour
JrBrowzer, Aug 2026
Shaka is a Great Boston Guide
If you're looking to trek the Freedom Trail at your own pace, I highly recommend downloading the Shaka App Boston Freedom Trail. The app guides you via map and narration to key stops along the trail. The narrative was engaging, fun and informational, and we were able to skip places we didn't care about seeing. The app is very intuitive and the map guidance works well. A really affordable way to get an extensive tour at your leisure. Plus they include tips for restrooms, places to rest, etc.
Read more
Boston Tours
Attractions
Guides
Calendar
View more
View more
View more
View more