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Top Florida Sailing Trips

106 Results
Key West Ultimate Beach Pass with Parasailing

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass. …More

Key West, USA

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass....

8 hours Free Cancellation
4.7 (19)
from
$107
Bimini or Grand Bahama Island Day Cruise

Just a 50-mile ferry ride from Florida, the beautiful Bahamas awaits! With over 700 stunning islands, this tropical paradise is famous for white-sand beaches, crystal-clear …More

Likely to Sell Out
Likely to Sell Out
Fort Lauderdale, USA

Just a 50-mile ferry ride from Florida, the beautiful Bahamas awaits! With over 700 stunning islands, this tropical paradise is famous for white-sand beaches, crystal-clear...

12 hours Free Cancellation
3.7 (24)
from
$265
Key West Sail and Snorkel Day Trip from Fort Lauderdale

Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it out for the first time! This day trip from …More

Fort Lauderdale, USA

Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it out for the first time! This day trip from...

15 hours Free Cancellation
3.4 (14)
from
$149
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
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 hours 30 minutes (approx.) Free Cancellation
$2,399
$2,270
Private Dolphin Sightseeing Sail on the Lazy Daze Catamaran

Join us for a Private Charter aboard the 41-foot catamaran Lazy Daze and experience fun dolphin sightseeing as we sail in the shimmering waters of …More

Panama City Beach, USA

Join us for a Private Charter aboard the 41-foot catamaran Lazy Daze and experience fun dolphin sightseeing as we sail in the shimmering waters of...

1 hour 30 minutes Free Cancellation
from
$857
All Inclusive Full Day and Sunset Private Catamaran in St. Pete

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter …More

St Petersburg, USA

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter...

8 hours Free Cancellation
from
$2,200

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