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Top Massachusetts Boat Tours

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Massachusetts Tours

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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
Boston, USA
4.6 (9,753)

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 (9,753)
from
$62
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

Boston, USA
4.6 (1,455)

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 (1,455)
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
Boston, USA
4.8 (789)

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 (789)
from
$40
Whale Watching Tour in Gloucester

You are guaranteed whale sightings on this whale watching tour out to Stellwagen Bank, a national marine preserve about 12 miles off the coast of …More

Likely to Sell Out
Likely to Sell Out
Gloucester, USA
4.9 (4,554)

Whale Watching Tour in Gloucester

You are guaranteed whale sightings on this whale watching tour out to Stellwagen Bank, a national marine preserve about 12 miles off the coast of...

4 hours • Free Cancellation
4.9 (4,554)
from
$48
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
Boston, USA
4.7 (705)

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 (705)
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

Boston, USA
4.5 (477)

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 (477)
from
$56
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
Boston, USA
4.8 (642)

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 (642)
from
$54
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
Boston, USA
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 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
Boston, USA
4.9 (180)

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 (180)
from
$82
Sailing on Historic Schooner Yacht in Salem, MA

Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience the majesty aboard John G. Alden's personal schooner yacht Malabar X. …More

Salem, USA
5.0 (265)

Sailing on Historic Schooner Yacht in Salem, MA

Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience the majesty aboard John G. Alden's personal schooner yacht Malabar X....

2 hours • Free Cancellation
5.0 (265)
from
$58
Boston Harbor Narrated Sunset Cruise

Escape the heat and enjoy amazing views of Boston’s beautiful skyline and the historic USS Constitution as the sun sets behind the city. As evening …More

Likely to Sell Out
Likely to Sell Out
Boston, USA
4.4 (525)

Boston Harbor Narrated Sunset Cruise

Escape the heat and enjoy amazing views of Boston’s beautiful skyline and the historic USS Constitution as the sun sets behind the city. As evening...

1 hour 30 minutes • Free Cancellation
4.4 (525)
from
$29
Boston Harbor Sightseeing Cruise

Cruise around Boston Harbor on classic 1920s-style Yacht Northern Lights. Relax in the indoor grand salon area or venture to the top, outdoor deck for …More

Likely to Sell Out
Likely to Sell Out
Boston, USA
4.6 (255)

Boston Harbor Sightseeing Cruise

Cruise around Boston Harbor on classic 1920s-style Yacht Northern Lights. Relax in the indoor grand salon area or venture to the top, outdoor deck for...

1 hour 30 minutes • Free Cancellation
4.6 (255)
from
$46
Boston Harbor Brunch Cruise

Enjoy a delicious 2-hour brunch cruise and take in historic sights along the water including Castle and Deer Island, Spectacle Island, Long Island, Lovells Island, …More

Boston, USA
4.6 (162)

Boston Harbor Brunch Cruise

Enjoy a delicious 2-hour brunch cruise and take in historic sights along the water including Castle and Deer Island, Spectacle Island, Long Island, Lovells Island,...

2 hours • Free Cancellation
4.6 (162)
from
$106
Kayak The Creek Nature Tour

RideAway Adventures has been awarded the best tours on Cape Cod 12 years in a row. We have the only fully ACA certified guide staff …More

Likely to Sell Out
Likely to Sell Out
Cape Cod, USA
4.9 (54)

Kayak The Creek Nature Tour

RideAway Adventures has been awarded the best tours on Cape Cod 12 years in a row. We have the only fully ACA certified guide staff...

2 hours • Free Cancellation
4.9 (54)
from
$80
Boston Holiday Cocoa Cruise

Enjoy a festive Christmas cruise aboard a classic yacht decorated for the holidays and cruise into an evening of skyline views, holiday music and some …More

Likely to Sell Out
Likely to Sell Out
Boston, USA
4.7 (81)

Boston Holiday Cocoa Cruise

Enjoy a festive Christmas cruise aboard a classic yacht decorated for the holidays and cruise into an evening of skyline views, holiday music and some...

1 hour 30 minutes • Free Cancellation
4.7 (81)
from
$65
City Cruises Boston Signature Lunch Cruise

Enjoy the Boston skyline with Boston's Signature Lunch Cruise - perfect for family sightseeing, lunch dates, and more. Enjoy our delicious lunch buffet, cocktails, wine, …More

Boston, USA
4.5 (133)

City Cruises Boston Signature Lunch Cruise

Enjoy the Boston skyline with Boston's Signature Lunch Cruise - perfect for family sightseeing, lunch dates, and more. Enjoy our delicious lunch buffet, cocktails, wine,...

2 hours • Free Cancellation
4.5 (133)
from
$83
Boston Historic Pubs Tour with Drinks and Tastings Included

Raise a pint to the spirits of Samuel Adams, Paul Revere and George Washington as you relive almost 400 years of Tavern History in Boston. …More

Boston, USA
4.9 (166)

Boston Historic Pubs Tour with Drinks and Tastings Included

Raise a pint to the spirits of Samuel Adams, Paul Revere and George Washington as you relive almost 400 years of Tavern History in Boston....

3 hours 30 minutes • Free Cancellation
4.9 (166)
from
$129
Cape Cod Explorer Tour

RideAway Adventures has been awarded the best tours on Cape Cod 12 years in a row. We have the only fully ACA certified guide staff …More

Likely to Sell Out
Likely to Sell Out
Cape Cod, USA
5.0 (19)

Cape Cod Explorer Tour

RideAway Adventures has been awarded the best tours on Cape Cod 12 years in a row. We have the only fully ACA certified guide staff...

2 hours • Free Cancellation
5.0 (19)
from
$80
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
City Cruises Boston Premier Dinner Cruise on Odyssey

Cruising year-round from Rowes Wharf, the sleek and modern Premier Dinner Cruise on Odyssey is the perfect setting for celebrating with friends, connecting with colleagues, …More

Boston, USA
3.9 (193)

City Cruises Boston Premier Dinner Cruise on Odyssey

Cruising year-round from Rowes Wharf, the sleek and modern Premier Dinner Cruise on Odyssey is the perfect setting for celebrating with friends, connecting with colleagues,...

2 to 3 hours • Free Cancellation
3.9 (193)
from
$133

Frequently Asked Questions

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

Recent tour reviews
Smooth Sailing
New York City
Sailing on Historic Schooner Yacht in Salem, MA
Audrey_G, Sep 2026
Smooth Sailing
Excellent and knowledgeable crew. All the other guests enjoyed. Lovely views. Had an amazing time!!!
Read more
Fun! Friendly crew
New York City
Classic Tall Ship Cruise in Boston Harbor
Sharon_G, Sep 2026
Fun! Friendly crew
Lots of fun. Good view of Boston harbor. Crew was very knowledgeable and friendly. Bring a jacket since it got a little chilly.
Read more
A perfect Saturday morning start to our girls's trip to Salem
New York City
Sailing on Historic Schooner Yacht in Salem, MA
karenoK8141DZ, Sep 2026
A perfect Saturday morning start to our girls's trip to Salem
A perfect way to experience Salem. The crew was friendly, experienced and helpful. The boat was amazing, and a wonderful addition to our girls trip weekend. The views were beautiful! Awesome trip, and I would definitely do it anytime I came to visit.
Read more
Perfect
New York City
Boston Duck Boat Sightseeing City Tour with Cruise
Catherine_M, Sep 2026
Perfect
It was a great day and narrator was great. So informative and funny made it very enjoyable…. Driver was excellent.
Read more
Very informative and the...
New York City
Classic Tall Ship Cruise in Boston Harbor
Nancy_C, Sep 2026
Very informative and the...
Very informative and the perfect amount of walking. A lot of information was given that I did not know before. Our guide, Kile, was awesome!!! Can’t say enough about his knowledge and the way he explained information. So good!
Read more
Will definitely do this again!!!
New York City
Whale Watching Tour in Gloucester
I1303NNcarolem, Sep 2026
Will definitely do this again!!!
Amazing trip!! We encountered whales within 25 minutes into the trip, and saw many more during tge tour!! The entire staff did a great job, the narrator alerted us when they spotted the whales, she also shared some great facts about the whales they are familiar with and a bit of their history as well. Definitely worth the price, parking is right at the boat. They do sell drinks and snacks- I think it’s cash only - we didn’t buy any..
Read more
Boston Harbor Sail
New York City
Sightseeing Day Sail around Boston Harbor
MaryAnnChuck_N, Sep 2026
Boston Harbor Sail
Working twin masted schooner with captain and crew. Witness first hand crew raising sails on the foremast, mainmast, foresail, and jib. Continues sail trimming, tacking as we changed directions, and ultimately lowering the sails as we headed back to dock. Crew friendly and knowledgeable answering all questions… very scenic trip around the harbor - bring your camera!
Read more
Quack Quack - This is a MUST
New York City
Boston Duck Boat Sightseeing City Tour with Cruise
shawn_n, Sep 2026
Quack Quack - This is a MUST
Great way to see the city and learn about its history in an easy comfortable way. We went on an 11am tour and our guide Vito was fantastic. He made it fun and interesting.
Read more
Great view of Boston from the water
New York City
City Cruises Boston Historic Sightseeing Harbor Cruise
Barb_H, Sep 2026
Great view of Boston from the water
We had a lovely cruise! It was wonderful to see Boston from the water. Our guide/narrator was very informative and enthusiastic. I would definitely recommend this activity.
Read more
Wonderful
New York City
City Cruises Boston Historic Sightseeing Harbor Cruise
Q6814QYlarryw, Sep 2026
Wonderful
Very good trip got to see everything!
Read more
Our afternoon sail was...
New York City
Sightseeing Day Sail around Boston Harbor
Antonio_V, Sep 2026
Our afternoon sail was...
Our afternoon sail was cancelled due to the weather but these hosts made everything right! They called to let me know my options and I was able to get a sunset cruise the next day. Ship was in great condition and the hosts on the ship were knowledgeable and fun to speak with. Kept the atmosphere right with drinks and blankets on board.
Read more
We saw so many whales....
New York City
Whale Watching Tour in Gloucester
Robin_H, Sep 2026
We saw so many whales....
We saw so many whales. The only negative was the waters choppy when you actually stop to see the whales so if you have motion sickness be prepared. People did get nauseous on the boat.
Read more
Big Al’s Historic Crawl
New York City
Boston Historic Pubs Tour with Drinks and Tastings Included
Barron_N, Sep 2026
Big Al’s Historic Crawl
This is a great time to learn a little history, have a few drinks, meet a few friends, and really appreciate Boston! Big Al is the man! Or as we would call him in San Diego, Grande Al!
Read more
Great evening. Guide did...
New York City
City Cruises Boston 90-Minute Harbor Sunset Sightseeing Cruise
Larry_D, Sep 2026
Great evening. Guide did...
Great evening. Guide did a great job. Very informative and humorous. We enjoyed our time. Highly recommended
Read more
Great cruise
New York City
City Cruises Boston 90-Minute Harbor Sunset Sightseeing Cruise
Patty_M, Sep 2026
Great cruise
Beautiful views and guide extraordinary. Boston is beautiful at night. Ride was smooth and saw cannons off old ironsides
Read more
Great experience
New York City
City Cruises Boston Premier Dinner Cruise on Odyssey
lauraW8488UH, Sep 2026
Great experience
We had a great time, a lot of fun of a special occasion or a fun night out.
Read more
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