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 Luxury Tours

246 Results
Sort by:
Featured
Filter
Languages Clear
Time of Day Clear
199
138
93
Duration Clear
12
177
72
4
4
Price Clear
$0 $500+
Rating Clear
153
227
235
Specials Clear
216
63
1
97
9
Features Clear
66
100
205
1
230
34
Accessibility Clear
35
168
202
Families Clear
112
144
51

Boston Tours

Attractions

Guides

Calendar

Boston Duck Boat Sightseeing City Tour with Cruise

Water is no barrier for a duck, why should it be for you? A Boston Duck Tour is a wonderful way to get a great …More

Likely to Sell Out
Likely to Sell Out
4.6 (9,765)

Boston Duck Boat Sightseeing City Tour with Cruise

Water is no barrier for a duck, why should it be for you? A Boston Duck Tour is a wonderful way to get a great...

1 hour 20 minutes • Free Cancellation
4.6 (9,765)
from
$62
Boston Ghosts and Gravestones Trolley Tour

Join other adventure seekers and become an apprentice grave digger on an entertaining tour through the darker side of Boston. A scary, fun and informative …More

4.5 (2,626)

Boston Ghosts and Gravestones Trolley Tour

Join other adventure seekers and become an apprentice grave digger on an entertaining tour through the darker side of Boston. A scary, fun and informative...

2 hours • Free Cancellation
4.5 (2,626)
from
$46
Boston Hop-On Hop-Off Trolley Tour with 13 Stops

Sit back and relax as expert tour guides turn back the pages of history and highlight the modern wonders of Boston – one of America’s …More

4.4 (5,714)

Boston Hop-On Hop-Off Trolley Tour with 13 Stops

Sit back and relax as expert tour guides turn back the pages of history and highlight the modern wonders of Boston – one of America’s...

30 to 120 minutes • Free Cancellation
4.4 (5,714)
from
$51
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 (3,656)

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 (3,656)
from
$23
City Cruises Boston Historic Sightseeing Harbor Cruise

See the sights. Experience the history. Boston's inner and outer harbors are awash in legend and lore, not to mention beauty. On this fully narrated …More

4.6 (1,458)

City Cruises Boston Historic Sightseeing Harbor Cruise

See the sights. Experience the history. Boston's inner and outer harbors are awash in legend and lore, not to mention beauty. On this fully narrated...

1 hour • Free Cancellation
4.6 (1,458)
from
$46
Classic Tall Ship Cruise in Boston Harbor

Come out for a day sail adventure in Boston Harbor aboard one of our classic wooden schooners, Liberty Star or Fame. Get away from the …More

Likely to Sell Out
Likely to Sell Out
4.8 (791)

Classic Tall Ship Cruise in Boston Harbor

Come out for a day sail adventure in Boston Harbor aboard one of our classic wooden schooners, Liberty Star or Fame. Get away from the...

90 to 120 minutes • Free Cancellation
4.8 (791)
from
$40
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

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 to Martha's Vineyard Day Trip with Optional Island Tour

We are proud to offer Boston's ORIGINAL Martha's Vineyard Day trip. Since 2011 we have been Boston's #1 day trip service to the island. Our …More

4.5 (3,226)

Boston to Martha's Vineyard Day Trip with Optional Island Tour

We are proud to offer Boston's ORIGINAL Martha's Vineyard Day trip. Since 2011 we have been Boston's #1 day trip service to the island. Our...

12 hours • Hotel pickup offered • Free Cancellation
4.5 (3,226)
from
$129
Historic Boston Hop-On Hop-Off Narrated Trolley Tour

Ride Boston's affordable trolley tour! CityView's silver trolleys take you through the streets of Boston and take in the highlights with a convenient and easy …More

4.5 (2,849)

Historic Boston Hop-On Hop-Off Narrated Trolley Tour

Ride Boston's affordable trolley tour! CityView's silver trolleys take you through the streets of Boston and take in the highlights with a convenient and easy...

1 hour 20 minutes • Free Cancellation
4.5 (2,849)
from
$48
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 (2,717)

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 (2,717)
from
$26
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 (2,893)

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 (2,893)
from
$59
Boston Harbor Sunset Cruise

Enjoy a relaxing sunset cruise in Boston Harbor which heads out to Fort Independence located on Castle Island and named after George Washington. Then take …More

Likely to Sell Out
Likely to Sell Out
4.7 (708)

Boston Harbor Sunset Cruise

Enjoy a relaxing sunset cruise in Boston Harbor which heads out to Fort Independence located on Castle Island and named after George Washington. Then take...

2 hours • Free Cancellation
4.7 (708)
from
$54
City Cruises Boston 90-Minute Harbor Sunset Sightseeing Cruise

After a busy day sightseeing or working, what could be nicer than relaxing onboard one of Boston's finest boats for a cruise on the harbor? …More

4.5 (479)

City Cruises Boston 90-Minute Harbor Sunset Sightseeing Cruise

After a busy day sightseeing or working, what could be nicer than relaxing onboard one of Boston's finest boats for a cruise on the harbor?...

1 hour 30 minutes • Free Cancellation
4.5 (479)
from
$56
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 (758)

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 (758)
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 (1,657)

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 (1,657)
from
$66
Sightseeing Day Sail around Boston Harbor

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of …More

Likely to Sell Out
Likely to Sell Out
4.8 (643)

Sightseeing Day Sail around Boston Harbor

Choose between either a 1.5 or 2-hour sail around Boston Harbor aboard one of our beautiful schooner Adirondack sailboats! These classic boats are reminiscent of...

90 to 120 minutes • Free Cancellation
4.8 (643)
from
$54
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
Sunset Sailing Cruise on a Tall Ship in Boston Harbor

If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise on a classic …More

Likely to Sell Out
Likely to Sell Out
4.7 (468)

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

If Boston is best seen from the water, then by far the best time to see it is during a sunset cruise on a classic...

2 hours • Free Cancellation
4.7 (468)
from
$71
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 (1,394)

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 (1,394)
from
$70
Boston Harbor Sunset Sail Tour

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. …More

Likely to Sell Out
Likely to Sell Out
4.9 (182)

Boston Harbor Sunset Sail Tour

Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon....

2 hours • Free Cancellation
4.9 (182)
from
$82

Frequently Asked Questions

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

Recent tour reviews
Very experienced guide....
New York City
The Full Revolutionary Story Epic Small-Group Boston Walking Tour
Janice_N, Sep 2026
Very experienced guide....
Very experienced guide. You’ll learn about the true history of the revolutionary war and the founding of Boston.
Read more
Very good very...
New York City
Boston Hop-On Hop-Off Trolley Tour with 13 Stops
Linda_E, Sep 2026
Very good very...
Very good very informative Hummer and Pudge really made it interesting and pointed out some great things. Highly recommend to everyone who visits the area.
Read more
Worth every penny. The...
New York City
Boston Freedom Trail Walking Tour with Costumed Guide
Kristen_E, Sep 2026
Worth every penny. The...
Worth every penny. The guide went above and beyond even during a nor’easter. The tour was educational, entertaining, and inspiring. Highly recommend!
Read more
This is a must on your calendar.
New York City
Boston Duck Boat Sightseeing City Tour with Cruise
Richard_R, Sep 2026
This is a must on your calendar.
This tour gives you an extremely entertaining history lesson about Boston, its origins, neighborhoods, and its notable citizens.
Read more
Great sunset cruise
New York City
Boston Harbor Sunset Cruise
Tricia_D, Sep 2026
Great sunset cruise
Great value for all we got to see and experience! Beautiful sunset cruise! The captain and crew were very knowledgeable and we got to be apart of the sounding of the cannon from the US Constitution!
Read more
Great experience in Boston
New York City
Boston Hop-On Hop-Off Trolley Tour with 13 Stops
O978AAangelar, Sep 2026
Great experience in Boston
Even though the weather was horrible with the rain, Old Town Trolley Tours completely saved our day in Boston! Brian was an incredible help and cleared up all of our confusion with our tickets right away. Once we were on board, we absolutely loved our driver, Beanie. She was so much fun, incredibly informative, and kept us thoroughly entertained despite the downpour. They turned a rainy day into a fantastic experience—highly recommend!
Read more
Tyler is a Gem
New York City
The Full Revolutionary Story Epic Small-Group Boston Walking Tour
jeffreybpatterson, Sep 2026
Tyler is a Gem
Tyler was a phenomenal guide. Personable, good story teller, extremely knowledgeable. Nice young man.
Read more
Must do
New York City
Boston’s Politically Incorrect North End Food Tour
Extraordinary44297, Sep 2026
Must do
Anthony is a fantastic guide with a personality. Great stories, mixed with a persona of spunk equals eventful tour. Must do, F bombs and all.
Read more
Do this tour!
New York City
Boston’s Politically Incorrect North End Food Tour
Derrick_S, Sep 2026
Do this tour!
Flash does just as advertised. We ate delicious food I would not have found on my own as an out-of-state visitor. Guide gives interesting history of the North End and Italian immigrants. Do not attend if cursing offends you. Guide also smokes at times between stops. Bring a drink for time's sake if you don't like water.
Read more
Everything was well...
New York City
Boston to Martha’s Vineyard Day Trip with Optional Island Tour
Kathy_W, Sep 2026
Everything was well...
Everything was well planned and organized, even though there was bad weather moving in. Would use Cool Destinations again and recommend to others.
Read more
Very informative. Our...
New York City
Boston Freedom Trail Walking Tour with Costumed Guide
Karen_F, Sep 2026
Very informative. Our...
Very informative. Our guide was energetic and took care of his group. His stories drew in his audience Thoroughly enjoy the walk.
Read more
10/10
New York City
Boston Harbor Sunset Cruise
elizabethhN1691FD, Sep 2026
10/10
Very nice boat, loved the history lessons over the PA. Caption was very funny. Good drinks and great service as well! Would recommend for sure.
Read more
5pm on a Friday = traffic! But this tour guide filled it wonderfully!
New York City
Boston Duck Boat Sightseeing City Tour with Cruise
J6478OEsarahh, Sep 2026
5pm on a Friday = traffic! But this tour guide filled it wonderfully!
This was an incredibly informative and FUN tour. Lots of history but also tidbits of fun facts! We didn't think that a 5pm boat tour on Friday = lots of traffic, but MAN! Our tour guide Birdie filled roughly 40 minutes of extra time with AMAZING information and to that I tip my hat. Well done on the improv front!
Read more
Fun in the rain
New York City
Boston Ghosts and Gravestones Trolley Tour
Michelle_S, Sep 2026
Fun in the rain
Had a fantastic time! The tour guides were so funny and knowledgeable about the history of Boston. Made the whole trip a blast.
Read more
Day on Martha's Vinyard
New York City
Boston to Martha’s Vineyard Day Trip with Optional Island Tour
Linda_W, Sep 2026
Day on Martha's Vinyard
Our trip from Boston to Martha's Vinyard was a very long, but good day. Because of the distance we had to leave very early and got back about 7:45pm due to traffic. I don't you could see it any other way. We did take the optional 3 hour island tour, it was worth it. Our guides were both very good and excellent drivers.
Read more
Perfect Harvard Tour
New York City
Harvard University Campus Guided Walking Tour
Paradise41375342533, Sep 2026
Perfect Harvard Tour
A great way to see Harvard. Amelia really knows her stuff and ran a great tour!
Read more
Boston Tours
Attractions
Guides
Calendar
View more
View more