Key West Sailing Charters & Tours
Set sail on a private sailing charter & tour in Key West and immerse yourself in the breathtaking beauty of this island paradise from the water. Whether you're enjoying a romantic sunset sail with your loved one, sipping champagne as the sun dips below the horizon, or embarking on an exciting day of exploration, Key West's calm, crystal-clear waters provide the perfect backdrop. Glide past the iconic coastline, spot dolphins playing in the waves, and explore the nearby waters, including the famous reef systems and secluded islands. These sailing tours are tailored to your preferences, ensuring an unforgettable, personalized experience that highlights the best of Key West’s natural beauty and vibrant marine life.
Featured Sailing Charters & Tours in Key West
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Jan 31 - Feb 6
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Private Trip
Public Trip
Swim Friendly
Cruise Only
Restroom
Captain Included
1-6 passenger
13-20 passenger
21-40 passenger
41-75 passenger
75+ passenger
Half Day Trip (if duration 3-6 hour)
Kid Friendly
Water Toys Available
Morning Departure (5am-11:59am)
Afternoon Departure (12pm-4:49pm)
Evening Departure (4:49-11:59pm)
Air Controlled Cabin
Food/Drink Available
Live Music
Kid Friendly (All Ages)
80
Key West: Southernmost Sunset Sail with Live Music & Hors d’oeuvres
4.7(211)
2 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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52
Key West: Rise & Reef Snorkeling Trip With Breakfast & Unlimited Mimosas
4.5(39)
3 Hrs.
Embark on an unforgettable snorkeling adventure to explore Florida's best reef aboard the Sandie Cat, Key West’s newest and fastest catamaran. Spend less time traveling and more time in the crystal-clear waters. Enjoy a complimentary breakfast, unlimited mimosas (mango, strawberry, and orange), and draft beer during this all-inclusive experience. Join the crew for a true Key West experience with family and friends. Reserve your spot today!
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86 80
Key West: Sunset Cruise with Live Music & Cocktails Included
4.9(85)
2 Hrs.
Sail away with an ocean breeze for a night of music, drinks, and dancing on this Live Music Sunset Cruise in Key West, Florida. Experience some of Key West’s best musicians as you dance to the backdrop of a gorgeous, tropical sunset. Eat, drink, and be merry aboard a spacious and comfortable catamaran and take in all of the stunning sights and sounds. For an evening you'll want to last forever, set sail on this Live Music Sunset Cruise! Book your experience today!
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57
Key West: Dip and Sip Snorkeling Adventure with Open Bar Included
4.7(55)
3 Hrs.
Take an afternoon and plunge into the depths of Florida's coral reef for an amazing snorkeling experience. The Sandie Cat is Key West's newest snorkeling catamaran, which allows you to get to the reef with speed, comfort, and some serious style. Join the captain and crew, round up your group, and hit the waves for an unforgettable Key West experience packed with fun, sun, and tasty spirits. This all-inclusive trip boasts an open well bar including unlimited mimosas (mango, strawberry & orange) & a variety of soft drinks! Book your spot today!
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79
Key West: Sunset Sip and Sail with Open Bar and Live Music
4.8(53)
2 Hrs.
Have you ever seen Key West at dusk on the open ocean? Just sit back on a Sunset Sip and Sail with Open Bar and Live Music and immerse yourself in the ambiance of this nightlife experience. You can dance the night away to live music while you sail the calm waters. Enjoy the best seat in the house with all of the good time essentials like draft beer, live music, open well bar, and appetizers. Book your spot now!
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117
Key West: Sunset Sail Aboard the Historic When and If
5.0(20)
2 Hrs.
Set sail on Key West’s most elegant historic schooner, the When and If. Built in 1939 for General George Patton’s dream of sailing around the world “When and If” he was able, is available to the public for the first time in the yacht's lifetime. Sit back and experience the beautiful Key West sunset in style as the wooden schooner glides through the water driven by wind power alone. Meet the crew as they serve up a beautiful array of gourmet cheeses and share their stories of old Key West and the sea. Book your Sunset Sail today!
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425
Key West: Harbor Day Sail Aboard the High Tide
5.0(2)
1.5 Hrs.
Cruise the scenic water of America's southernmost city on a private day sail adventure with the professionals at Sunset Sail Key West. From the history of Mallory Square and Fort Zachary Taylor to the natural beauty of Key West's National wildlife preserve, this comprehensive sightseeing cruise is the perfect way to experience picturesque sailing in Key West with your family or friends. Relax with a drink, take in the scenery, or test your hand at sailing the ship! Don't miss the fun, book today!
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100
Key West: Windjammer Schooner Champagne Sunset Sail
5.0(1)
2 Hrs.
Spend a romantic evening aboard an authentic wooden schooner on this Windjammer Schooner Sunset Sail in Key West, Florida. This sailing vessel is fit for royalty, with its wide decks and ample seating and includes an open bar. Journey in comfort to landmark sites like the Navy Mole, Fort Zachary Taylor, Sunset Key, and more as the sails are hoisted and the tropical breeze whisks your cares away. Witness the beauty of a Key West Sunset and behold the grandeur of the star-filled Southern sky on this cruise. Book today!
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55
Key West: Windjammer Schooner Day Sail with Complimentary Beverages Included
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2 Hrs.
Catch the wind on an historic, dual-masted sailing vessel for a pleasure cruise through beautiful Key West, Florida with a Windjammer Schooner Day Sail. Journey the calm, tropical waters to view landmark sites like Fort Zachary Taylor, the Navy Mole, and opulent Sunset Key. Sample a wide variety of premium complimentary drinks like homemade sangria, draft beer, premium wine, and more. Climb aboard an authentic sailing schooner for this luxurious day sail and cast your cares into the warm breeze. Book your spot today on this Windjammer Schooner Day Sail.
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747
Key West: Chill Out Sail with Lily-Pad
5.0(2)
3 Hrs.
Live the Key West lifestyle as you set sail over calm blue waters then drop anchor and chill out on a giant floating lily pad. Enjoy this unique private adventure with family and friends, away from the crowds. Be sure to take in all of Key West's beauty while relaxing and soaking up the sun from the water. Book today and set out on a private sailing adventure.
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60
Key West: Catamaran Champagne Sunset Sail
4.9(101)
1.5 Hrs.
Set sail on a Catamaran Champagne Sunset Sail in Key West for an unforgettable evening. Sip complimentary drinks as the ocean breeze carries you into a breathtaking sunset, fading into a star-filled sky. Whether with family or someone special, relax, unwind, and savor the beauty of Key West. Book your Champagne Sunset Sail today!
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45
Key West: Morning Reef Snorkel and Sail with Unlimited Mimosas
5.0(34)
3 Hrs.
Imagine yourself swimming in the warm tropical water of Key West, Florida with swarms of vibrant colorful fish all around you as you begin the day with a Morning Reef Snorkel and Sail with Unlimited Mimosas aboard an expansive 69’ sailing catamaran. Sail seven miles off Key West’s majestic coast to the shallow Caribbean water of the Florida Keys Reef. Set off on this adventure and book your spot today.
Read moreBooked 2 times in last 48 hrs