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Key West Sailing Charters

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Champagne Sunset Catamaran Cruise

Champagne Sunset Catamaran Cruise

98 ratings
Duration1.5 Hrs.
Enjoy a night you’ll never forget on a Champagne Sunset Catamaran Cruise in Key West. Watch the masterfully painted sunset fade into dark as the stars give an encore unlike any other. Stretch out and enjoy a pampering of complimentary drinks with family or a special someone. Come feel the ocean breeze blow through your hair and dance across your skin as the sun sets over Key West, book your Champagne Sunset Sail today!
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from
$64
Experience Today
Southernmost Sunset Sail with Bar and Hors d’Oeuvres

Southernmost Sunset Sail with Bar and Hors d’Oeuvres

203 ratings
Duration2 Hrs.
Entice yourself with the starburst blaze of colors that is the Key West sunset on a luxurious sunset sail. See local landmarks and sail past Sunset Key and historic Fort Zachary Taylor as you dine on a tasty selection of varied hors d'oeuvres. Watch the sunset with your favorite drink in your hand and your loved ones by your side. Enjoy live music from local musicians! These are moments you’ll savor long after you leave town! Don't miss the boat. Book your spot today!
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from
$74
Experience Today
Snorkel & Sail Adventure on the Floridays

Snorkel & Sail Adventure on the Floridays

New to TripShock
Duration3 Hrs.
Set sail on a journey to the only living coral barrier reef in the continental United States with this Snorkel & Sail Adventure on the Floridays! Spend the first hour sailing on the beautiful Key West water in a 54-foot yacht, feeling the breeze and warmth of the sun on your skin. Once at the reef, have some fun and snorkel the surrounding area. Admire the world under the water as you get the chance to see this coral barrier reef and the marine life that calls this place home! As you travel back to the Florida coast, enjoy complimentary drinks as you reminisce with family and friends about your time at the reef. Don't miss out on this once in a lifetime adventure, book your experience now!
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New to TripShock

from
$79
per ticket
Experience Today
Key West Private Sunset Sailing Cruise

Key West Private Sunset Sailing Cruise

New to TripShock
Duration3 - 6 Hrs.
Get ready to sail in luxury aboard your own private 44-foot catamaran. Sail to your heart's content in the open ocean in the Gulf of Mexico on your 3 or 6 hour sailing excursion and end the day watching the sunset in all of its striking glory. Catered completely to your preferences, have your day your way. Whether you want to paddleboard, swim, or just cruise around and sightsee, this is a great trip for the whole family to be entertained. Grab a drink and feel the warm breeze in your hair. Book your Key West Private Sunset Sailing Cruise experience today!
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New to TripShock

from
$800
per charter
Next Available:
Monday
Key West Sunset Sail on Schooner Jolly II Rover

Key West Sunset Sail on Schooner Jolly II Rover

New to TripShock
Duration2 Hrs.
End your day soaking in the sights and sounds of the emerald waves on this Sunset Sail on the Schooner Jolly II Rover. Witness the beauty of Key West, Florida as you admire the sunset from the decks of a schooner. Watch for Florida wildlife, dolphins, turtles, flying fish, pelicans, and more as you coast through the ocean. Help raise the sails, fire the cannons, and take your turn at the wheel for an authentic sailing experience. Enjoy an exciting sailing experience and take in the amazing views. Book your tickets today!
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New to TripShock

from
$85
per ticket
Experience Today
Morning Reef Snorkel and Sail in Key West

Morning Reef Snorkel and Sail in Key West

31 ratings
Duration3 Hrs.
Begin the day in the lap of luxury on an expansive 69’ sailing catamaran with Sebago Watersports. First, you’ll sail seven miles off Key West’s majestic coast to the shallow Caribbean water of the Florida Keys Reef. Imagine yourself swimming in warm tropical waters with swarms of vibrant colorful fish all around you. Set off on an adventure and book your Morning Reef Snorkel with Sebago Watersports today.
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from $50
$42
Experience Today
Private Snorkel and Sunset Sail Excursion

Private Snorkel and Sunset Sail Excursion

1 rating
Duration4 Hrs.
Climb aboard and set out on a private snorkel and sunset sail. You'll get the best of both worlds as you glide across the water in classic sail boat before jumping in magical blue waters to snorkel and explore the underwater ecosystems off the coast of Key West. Then wrap it all up with a world famous Key West sunset. The perfect way to spend time with friends and family, book your private snorkel and sunset sail today.
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from
$895
per boat
Experience Tomorrow
Wind and Wine Sunset Sail

Wind and Wine Sunset Sail

67 ratings
Duration2 Hrs.
Sail into an unforgettable Key West sunset while sampling beer, delicious hors d'oeuvres, and 8 fine wines from around the world. Rated one of the top two sunset tours in all of North America by Coastal Living Magazine, this luxurious Wind and Wine Sunset Sail on a historic Schooner will not disappoint. Make some new friends, enjoy tropical music, and delight your palate as you watch the sun melt into the water. Book your spot today!
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from
$109
Experience Today
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FREQUENTLY ASKED QUESTIONS

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