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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Jul 4 - Jul 10
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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)
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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45
Key West: Morning Reef Snorkel and Sail with Unlimited Mimosas
5.0(33)
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.
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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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91
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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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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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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64
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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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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60
Key West: Afternoon Reef Snorkel and Sail Aboard a Luxury Catamaran
5.0(1)
3 Hrs.
Immerse yourself in the tropical water of Key West when you set out on a snorkel and sailing adventure. Watch swarms of colorful fish and marine wildlife swim around you as you explore the only living coral barrier reef in North America. The experienced captains will select the perfect reef based on the afternoon's water and wind variables so you can have the best snorkeling experience possible. See Key West's coral reef and book the Afternoon Reef Snorkel and Sail today!
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35
Key West: Morning Coral Reef Snorkel Adventure & Catamaran Cruise
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3 Hrs.
Experience some morning snorkeling in the sparkling water of the Florida Keys on this Morning Coral Reef Snorkel Adventure & Catamaran Cruise. Climb on board a luxurious state-of-the-art catamaran and journey to a nearby reef teeming with tropical fish. Enjoy sightseeing around North America’s only living coral reef as you soak in the wonders around you. Book today for the ultimate snorkeling experience and catamaran cruise in Key West!
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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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117
Key West: Afternoon Sail, Snorkel, & Kayak Adventure with Complimentary Beverages
5.0(5)
4.5 Hrs.
Get out on the water for an incredible day of sailing, kayaking, and snorkeling in one on this Key West Sail, Snorkel, & Kayak Adventure. Treat yourself to the island life as you climb aboard a 65-foot Schooner and kayak through the mangroves, then snorkel in the sky-blue waters off the shores of Key West. Experience a wealth of tropical wildlife in the air, on the land, and in the sea while you explore Key West's backcountry. Finish off your day with a famous Key West sunset. Don't miss the boat, book your Key West Sail, Snorkel, & Kayak Adventure today!
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