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Top USA Sailing Trips

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 …More

Likely to Sell Out
Likely to Sell Out
Key West, USA

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 (1,703)
$115
$99
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. …More

Likely to Sell Out
Likely to Sell Out
Key West, USA

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 (2,727)
from
$105
Key West Backcountry Safari

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

Likely to Sell Out
Likely to Sell Out
Key West, USA

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 (2,727)
from
$105
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 …More

Fort Lauderdale, USA

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
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 …More

Likely to Sell Out
Likely to Sell Out
Charleston, USA

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 (822)
from
$56
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 …More

Panama City Beach, USA

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 (4,998)
from
$52
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 …More

Key West, USA

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 (3,796)
from
$80
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 …More

Special Offer
Special Offer
Key West, USA

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

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 …More

Key West, USA

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

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 …More

Key West, USA

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

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

Key West, USA

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 (419)
from
$70
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 …More

Key West, USA

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

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 …More

Likely to Sell Out
Likely to Sell Out
Key West, USA

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

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 …More

Fort Lauderdale, USA

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

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

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 (786)
from
$40
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 …More

Panama City Beach, USA

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 (2,058)
from
$42
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, …More

Likely to Sell Out
Likely to Sell Out
Panama City Beach, USA

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 (747)
from
$45
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 …More

Likely to Sell Out
Likely to Sell Out
Oahu, USA

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

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 …More

Likely to Sell Out
Likely to Sell Out
Seattle, USA

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 (573)
from
$39
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 …More

Likely to Sell Out
Likely to Sell Out
Hilton Head Island, USA

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 (558)
from
$55

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