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Top USA Sailing Trips

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Key West Wind & Wine Sunset Sail
Likely to Sell Out
Likely to Sell Out
Key West, USA
5.0 (1,702)

Key West Wind & Wine Sunset Sail

Wind & Wine has been the #1 rated sunset sail on Cool Destinations for over a decade. In our opinion, this is the best wine...

2 hours (approx.) • Free Cancellation
5.0 (1,702)
$115
$99
Key West Sail, Snorkel, Kayak with Sunset Option
Likely to Sell Out
Likely to Sell Out
Key West, USA
4.9 (2,724)

Key West Sail, Snorkel, Kayak with Sunset Option

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge....

4.5 or 6.5 hours (approx.) • Free Cancellation
4.9 (2,724)
from
$105
Key West Backcountry Safari
Likely to Sell Out
Likely to Sell Out
Key West, USA
4.9 (2,724)

Key West Backcountry Safari

Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness....

4.5 or 6.5 hours (approx.) • Free Cancellation
4.9 (2,724)
from
$105
Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor
Likely to Sell Out
Likely to Sell Out
Charleston, USA
4.6 (816)

Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor

Meet us at Aquarium Wharf near Concord St. and Calhoun St. in Charleston SC as you experience historic Charleston Harbor aboard our classic 84-foot Tall...

1 hour 30 minutes • Free Cancellation
4.6 (816)
from
$56
1-Hour Interactive Pirate Cruise (arrive 30 minutes early)
Fort Lauderdale, USA
4.9 (1,527)

1-Hour Interactive Pirate Cruise (arrive 30 minutes early)

Prepare for high seas adventure on this fully interactive, family-friendly, 1-Hour Pirate Adventure Cruise (check in is a half hour before the sail time) along...

1 hour • Free Cancellation
4.9 (1,527)
from
$35
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time
Panama City Beach, USA
4.9 (4,989)

Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time

Experience the best of Panama City Beach on this 3-hour Shell Island snorkel and dolphin cruise aboard a spacious sailing catamaran. This family-friendly adventure includes...

3 hours • Free Cancellation
4.9 (4,989)
from
$52
Key West Sunset Sail with Live Music, Champagne, Hors D’oeuvres and Full Bar
Key West, USA
4.8 (3,794)

Key West Sunset Sail with Live Music, Champagne, Hors D’oeuvres and Full Bar

Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on a modern sailing catamaran...

2 hours (approx.) • Free Cancellation
4.8 (3,794)
from
$80
Key West Original Full-Day Watersports Adventure
Special Offer
Special Offer
Key West, USA
4.9 (739)

Key West Original Full-Day Watersports Adventure

This Key West experience lets you enjoy all that the island has to offer. Sail on a sleek catamaran along the smooth waters of the...

6 hours (approx.) • Free Cancellation
4.9 (739)
$200
$169
Key West Catamaran Dolphin Watch & Sunset Sail
Key West, USA
4.8 (744)

Key West Catamaran Dolphin Watch & Sunset Sail

Set sail from Key West's Historic Seaport for a thrilling dolphin watch and famous Key West sunset sail aboard a luxury catamaran with premium wines...

2 hours 30 minutes (approx.) • Free Cancellation
4.8 (744)
from
$90
Key West Schooner Sunset Sail with Hors D'oeuvres and Full Bar
Key West, USA
4.9 (1,701)

Key West Schooner Sunset Sail with Hors D'oeuvres and Full Bar

Meet for this Key West Sunset Sail at the Key West Historic Harbor. Board a beautiful bugeye schooner, and get acquainted with your captain and...

2 hours (approx.) • Free Cancellation
4.9 (1,701)
from
$100
Key West Signature Sunset Sail with Live Music, Open Bar & Food
Key West, USA
4.6 (418)

Key West Signature Sunset Sail with Live Music, Open Bar & Food

Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music •...

2 hours • Free Cancellation
4.6 (418)
from
$70
Key West Dolphin and Snorkel Experience
Key West, USA
4.7 (342)

Key West Dolphin and Snorkel Experience

The Cool DestinationsDolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world famous Key...

3 hours • Free Cancellation
4.7 (342)
from
$70
Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
Likely to Sell Out
Likely to Sell Out
Key West, USA
4.9 (1,701)

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key...

2 hours • Free Cancellation
4.9 (1,701)
from
$123
Sunset Catamaran Cruise in Ft. Lauderdale
Fort Lauderdale, USA
4.8 (701)

Sunset Catamaran Cruise in Ft. Lauderdale

A perfect way to end the day, with a relaxing sail upon the Atlantic Ocean. Imagine taking in the breathtaking views of FT. Lauderdale beach...

2 hours • Free Cancellation
4.8 (701)
from
$129
Classic Tall Ship Cruise in Boston Harbor
Likely to Sell Out
Likely to Sell Out
Boston, USA
4.8 (778)

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 (778)
from
$40
Waikiki 2 hour Turtle Canyon Snorkeling Adventure
Likely to Sell Out
Likely to Sell Out
Oahu, USA
4.8 (1,462)

Waikiki 2 hour Turtle Canyon Snorkeling Adventure

Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cruise along the stunning Waikiki coastline aboard the either...

2 hours • Free Cancellation
4.8 (1,462)
from
$81
Seattle Sailing Harbor Tour
Likely to Sell Out
Likely to Sell Out
Seattle, USA
4.8 (570)

Seattle Sailing Harbor Tour

Seattle's Tall Ship welcomes you aboard for a day sail on our classic schooner! Our Harbor Sailing tour is family-friendly and is an excellent way...

2 hours • Free Cancellation
4.8 (570)
from
$39
Dolphin Sunset Cruise in Panama City Beach on the "Island Time"
Panama City Beach, USA
4.9 (2,052)

Dolphin Sunset Cruise in Panama City Beach on the "Island Time"

The Dolphin Watching & Sunset Sail is a 2 hour cruise aboard the Island Time Sailing Catamaran which departs from the Lagoon Pontoons Marina in...

2 hours • Free Cancellation
4.9 (2,052)
from
$42
America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head
Likely to Sell Out
Likely to Sell Out
Hilton Head Island, USA
4.7 (556)

America's Cup 12-Meter Yacht Afternoon Sail from Hilton Head

Only on Hilton Head and only in Harbour Town can you sail aboard the real America's Cup, 12 meter, Stars & Stripes once skippered by...

1 hour 30 minutes • Free Cancellation
4.7 (556)
from
$55
Sunset Dolphin Sail Aboard the Privateer Catamaran
Likely to Sell Out
Likely to Sell Out
Panama City Beach, USA
4.8 (746)

Sunset Dolphin Sail Aboard the Privateer Catamaran

If you are looking to unwind before dinner or a night out on the town, come take a romantic Sunset Sail on the SV Privateer,...

2 hours • Free Cancellation
4.8 (746)
from
$45

Frequently Asked Questions

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

Recent tour reviews
Great experience
New York City
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time
Misty_F, Sep 2026
Great experience
This was a great experience, a must do! Nice boat ride, saw a few dolphins and my first time snorkeling and the crew was awesome!
Read more
Worth the cost - delightful day!
New York City
Shell Island Snorkel and Dolphin Catamaran Cruise with Island Time
H4561TVjoyr, Sep 2026
Worth the cost - delightful day!
We had a terrific time with Captain Heath and his two associates, Emily and Carter. They were informative, fun, kind and helpful. From the moment they invited us on the catamaran until we departed, we had a blast! We saw dolphins, enjoyed Shell Island, and enjoyed a perfect weather day! Worth every penny we paid!
Read more
Great day for sailing...
New York City
Classic Tall Ship Cruise in Boston Harbor
Anna_A, Sep 2026
Great day for sailing...
Great day for sailing despite being windy The staff very friendly and helpful... I have mobility issues and they made sure I boarded the boat with care... thankyou
Read more
Boston Long Boat Tour
New York City
Classic Tall Ship Cruise in Boston Harbor
derektG5476XL, Sep 2026
Boston Long Boat Tour
Captain Jack(not Sparrow) and crew did a fantastic job entertaining and providing a very relaxing experience around the bay
Read more
Great snorkeling.
New York City
Waikiki 2 hour Turtle Canyon Snorkeling Adventure
68teresitah, Sep 2026
Great snorkeling.
Disappointed that first was cancelled then when rescheduled again on our last day. Otherwise , it was awesome and will do it again hopefully on next visit if possible.
Read more
Anniversary Outing before Dinner
New York City
Dolphin Sunset Cruise in Panama City Beach on the “Island Time”
500kassandraa, Sep 2026
Anniversary Outing before Dinner
We booked the sunset dolphin cruise as part of our anniversary celebration, and it ended up being one of the highlights of our trip! We had such a great time and saw plenty of dolphins, but what really made the experience special was the crew.Conner and Emma were fantastic! They were friendly, fun, knowledgeable, and made sure everyone on board had a great experience. They created such a relaxed and enjoyable atmosphere and made our anniversary evening even more memorable.The sunset was beautiful, the dolphins were amazing, and the whole experience was exactly what we were hoping for. We would absolutely recommend this cruise—and a big thank you to Conner and Emma for making our anniversary celebration extra special! ❤️🐬
Read more
Great Way to See Seattle
New York City
Seattle Sailing Harbor Tour
Emily_V, Sep 2026
Great Way to See Seattle
A great way to see the Seattle skyline at a slower pace. The crew were all super friendly and helpful. The views in a clear day are spectacular!
Read more
Perfect sunset to watch the dolphins.
New York City
Dolphin Sunset Cruise in Panama City Beach on the “Island Time”
Z8482JKtracyt, Sep 2026
Perfect sunset to watch the dolphins.
10/10 I would recommend this. We got to see so many dolphins and the ships crew was amazing!
Read more
Just Awesome!
New York City
America’s Cup 12-Meter Yacht Afternoon Sail from Hilton Head
STEF464, Sep 2026
Just Awesome!
This was a bucket list experience that I didn't know I even had on my bucket list. in retrospect this is the second historical maritime vessel I have been on (the only other being the USS Constitution!). The weather was perfect (although the gusts were 25 to 30 mph - but fairly light chop. I had a ball at the helm! Captain Peter knows how to skipper a boat AND knows how to make everyone feel comfortable (and safe).
Read more
A great experience. Drinks dolphins and beautiful sunset.
New York City
Sunset Dolphin Sail Aboard the Privateer Catamaran
M4727YOrandyh, Sep 2026
A great experience. Drinks dolphins and beautiful sunset.
Captain was top notch. 1st mate and bartender (same guy) was too. Lots of dolphin sightings out there. Sunset was spectacular. A must go on. Two hours trip flies by.
Read more
It is a great little...
New York City
Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor
Patsy_P, Sep 2026
It is a great little...
It is a great little trip. Captain Anderson and his crew were very nice. It was great fun sailing, even if we didn’t get to see dolphins.
Read more
Turtles Galore!
New York City
Waikiki 2 hour Turtle Canyon Snorkeling Adventure
Teresa_F, Sep 2026
Turtles Galore!
We had a wonderful time on this catamaran sail. Jamie our captain was very sociable and informative. We felt very safe and well cared for by all the crew. This was September and we were surrounded by turtles. Plus it was a beautiful ride with views of Ohau. Great experience.
Read more
Dolphin Sail
New York City
Afternoon Schooner Sightseeing Dolphin Cruise on Charleston Harbor
Tereasa_H, Sep 2026
Dolphin Sail
Very relaxing sail. Both Daniels and Bennett were very nice young men. Got to see several dolphins at play during the morning cruise. Would highly recommend.
Read more
Great sailing adventure
New York City
America’s Cup 12-Meter Yacht Afternoon Sail from Hilton Head
susansU6323AL, Sep 2026
Great sailing adventure
It was a great sailing experience. The crew were very good and knew what they were doing.
Read more
It really was truly a...
New York City
Key West Signature Sunset Sail with Live Music, Open Bar & Food
JACK_S, Sep 2026
It really was truly a...
It really was truly a wonderful experience. The music that crew. The only thing that was annoying was the random kid, running all over the boat supervised. Someone should have addressed his parents
Read more
The perfect sailing tour
New York City
Seattle Sailing Harbor Tour
Jackie_S, Sep 2026
The perfect sailing tour
The crew was excellent, professional, entertaining, friendly. The crew provided safety information.. we were free to move around as long as we follow the instructions given by the crew. Although they had nothing to do with the weather, it was perfect. They were very engaging and the tour was very relaxing. I highly recommend this tour..
Read more
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