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.
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Jul 24 - Jul 30
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Private Trip
Public Trip/Individual Tickets
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(212)
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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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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117
Key West: Wind and Wine Sunset Sail Aboard a Historic Schooner
4.8(71)
2 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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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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106
Key West: Morning Sail, Snorkel, and Kayak Excursion with Complimentary Beverages
4.9(28)
4.5 Hrs.
Start your day with a serene escape into Key West’s natural wonders on this morning sail, snorkel, and kayak tour. Cruise aboard a spacious 65-foot schooner into the heart of the Florida Keys backcountry, where wildlife sightings are abundant and the water is shimmering. Paddle through winding mangrove tunnels in a guided kayak eco-tour, then snorkel over vibrant seagrass beds teeming with tropical fish, rays, and other marine life. Perfect for early risers looking to beat the crowds and experience the best of Key West’s outdoor activities in one unforgettable morning. Book your spot 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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64 62
Key West: Coral Reef Snorkeling Catamaran Trip with Margaritas Included
4.8(10)
3 Hrs.
Experience the best afternoon you'll find on the straits of the Florida Keys by snorkeling this gorgeous coral reef. Climb aboard a luxurious catamaran as you cruise the crystal water to North America's only living coral reef. Dive into the sparkling, tropical water for underwater exploration, teeming with brightly colored tropical fish and corals. You don't have to be a jet setter to have a world-class time, so book your trip on this Coral Reef Snorkeling Catamaran Trip with Margaritas Included today!
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125
Key West: Schooner Champagne Sunset Sail with Complimentary Beverages Included
5.0(11)
2 Hrs.
Come along on this Champagne Sunset Sail and step into luxury in Key West, Florida. Sip, relax, and unwind aboard a gorgeous wooden schooner. Enjoy your authentic sailing experience as you cruise the crystalline water to landmark sites while sampling a wide variety of complimentary drinks. Come toast to an idyllic Key West sunset on the schooner cruise that is sure to become your favorite new Key West tradition. Book yours today!
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144
Key West: Sail, Snorkel, and Kayak Excursion with Complimentary Beverages
5.0(12)
6.5 Hrs.
Get out on the water and experience nature at her finest with a Sail, Snorkel, and Kayak Excursion. You'll see an incredible array of birds, fish, and other regional wildlife while you explore Key West's backcountry and take in all the beauty around you. Live the island dream as you set sail on a 65-foot Schooner, then kayak through the mangrove forests. Snorkel the blue waters in search of tropical marine species. Book this Full Day Sail, Snorkel, and Kayak Excursion today and let your adventure begin!
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89
Key West: Snorkel & Sail Adventure on the Floridays with Complimentary Beverages Included
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3 Hrs.
Set sail on a 54-foot yacht in Key West, Florida for a scenic cruise to the only living coral barrier reef in the continental U.S. with this Snorkel & Sail Adventure on the Floridays. Cruise the water on an hour-long sail followed by snorkeling among vibrant marine life. Relax with complimentary drinks on the return trip as you cruise past the turquoise waters of the Florida coast. An unforgettable way to experience the natural beauty of Key West! Book now!
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135
Key West: Bugeye Schooner Backcountry Eco Tour Aboard the Appledore Star
5.0(1)
5 Hrs.
Have you ever wanted to take the wheel or hoist the sails of a real schooner? If so, here's your chance! This Bugeye Backcountry Tour is an amazing mix of sailing, snorkeling, and kayaking among the most scenic settings in the Florida Keys, including the Sponge Garden Reef and Mangrove Island. Discover the amazingly diverse ecosystem of Key West’s backcountry and observe the abundant wildlife from the water. This tour is a MUST for outdoor enthusiasts! Book your spot today!
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