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Top Key West Sailing Trips

40 Results
Key West Private Wind & Wine Charter

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Cool Shore Excursions three years running. See the sunset …More

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Cool Shore Excursions three years running. See the sunset...

2 hours (approx.) Free Cancellation
5.0 (1,715)
from
$3,499
Private Key West Morning Sail, Snorkel & Kayak Excursion

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

Special Offer
Special Offer

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

4 hours 30 minutes (approx.) Free Cancellation
$2,399
$2,270
Private Afternoon Snorkel with Sunset Sail in Key West

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon …More

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon...

4 hours Free Cancellation
5.0 (4)
from
$995
Key West Private Charter: Sandbar and Snorkeling

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a …More

Likely to Sell Out
Likely to Sell Out

This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a...

4 hours
5.0 (20)
from
$950
Private Sunset Sail in Key West Florida

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch …More

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch...

2 hours Free Cancellation
5.0 (1)
from
$750
Private Key West Sunset Sail

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for …More

2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for...

2 hours
4.9 (50)
from
$693
Private Key West Sandbar and Paddle by Boat

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats …More

Likely to Sell Out
Likely to Sell Out

Enjoy a private half day adventure for up to 6 guests aboard our late model pontoon boat. Guests may discover and observe diverse marine habitats...

3 hours 30 minutes Free Cancellation
5.0 (38)
from
$600
Private 90-Minute Harbor Sailing Charter in Key West

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida …More

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida...

1 hour 30 minutes Free Cancellation
4.9 (20)
from
$425
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

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: Sunset Sail + Reef Snorkel & Sandbar

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? • …More

Likely to Sell Out
Likely to Sell Out

Reef Snorkel + Sandbar & Sunset Sail • Summer Only with Small Groups on an Honest Eco Tour. What Makes this Eco Tour different? •...

4 hours 30 minutes Free Cancellation
5.0 (56)
from
$150
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

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 (1,702)
from
$127
Key West Wreckers Race Aboard Schooner America 2.0

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in …More

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in...

3 hours
4.9 (14)
from
$127
Key West Dolphin Watch and Sunset Sail on Catamaran

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of …More

Likely to Sell Out
Likely to Sell Out

Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the water, catching every gust of...

3 hours Free Cancellation
4.9 (40)
from
$124
Key West Full-Day Catamaran Eco Tour: Sail, Kayak and Dolphin Watch

Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and dolphin watching the perfect way to spend a …More

Special Offer
Special Offer

Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and dolphin watching the perfect way to spend a...

6 hours (approx.)
4.9 (558)
$125
$120
Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your …More

Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your...

5 hours Free Cancellation
4.9 (118)
from
$119
Key West Schooner Backcountry Eco-Tour

Set sail from Historic Seaport on the Key West Schooner Backcountry Eco-Tour adventure! …More

Set sail from Historic Seaport on the Key West Schooner Backcountry Eco-Tour adventure!...

5 hours (approx.) Free Cancellation
4.9 (216)
from
$110
Classic Key West Schooner Sunset Sail with Full Open Bar

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This …More

Likely to Sell Out
Likely to Sell Out

There's no better way to savor the magic of a Key West sunset than aboard a majestic schooner, complete with a full open bar. This...

2 hours Free Cancellation
4.9 (282)
from
$109
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne …More

Likely to Sell Out
Likely to Sell Out

Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne...

2 hours
4.9 (977)
from
$109
Shallow Water Snorkeling and Dolphin Watching in Key West

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s …More

Likely to Sell Out
Likely to Sell Out

Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s...

4 hours
4.8 (438)
from
$109
Champagne Dolphin Sail and Reef Snorkel

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with …More

Likely to Sell Out
Likely to Sell Out

Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with...

3 hours
5.0 (10)
from
$109

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