Key West Sailing

Set sail on the ocean blue with a luxury sailing excursion in Key West, Florida. An essential Key West activity, choose from sunset, champagne, snorkeling, and more. With private and public trips available, your perfect trip is only a few clicks away.
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Jun 13 - Jun 19
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Dolphin Watch Sunset Sail with Premium Wine and Tapas Pairings

114 ratings
2.5 Hrs.
Embark on an unforgettable sailing adventure through the crystal-clear waters of Key West with the Dolphin Watch Sunset Sail. Enjoy superbly crafted tapas like tuna poke and shrimp cocktail along with champagne, select premium wines including LaCrema, beer, and sangria as you journey to view majestic dolphins, landmark sights and the world famous Key West sunset. Get an authentic sailing experience as the captain and crew raise the sails on your luxurious catamaran and set out to find dolphins playing and frolicking in the surf and often near the boat! Book yours today!
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Champagne Sunset Catamaran Cruise

100 ratings
1.5 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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Southernmost Sunset Sail with Bar and Hors d’Oeuvres

211 ratings
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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Morning Reef Snorkel and Sail in Key West

32 ratings
3 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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Dip and Sip Afternoon Snorkel with Open Bar

53 ratings
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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Live Music Sunset Cruise with Cocktails Included

85 ratings
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 today!
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Key West Sunset Sail on America 2.0

45 ratings
2 Hrs.
Embark on a spectacular sunset sailing adventure off the coast of Key West, Florida in search of the famed "Green Flash." Experience the magic and romance of sailing at dusk as you sip champagne and watch for dolphins and other marine wildlife in the surf. Your friendly captain and crew will teach you the basics of sailing and even let you take the wheel. So, take a turn at the helm of one of the fastest schooners in the United States, book today!
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Wind and Wine Sunset Sail

71 ratings
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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Day Sail Aboard Schooner America 2.0

17 ratings
1.5 Hrs.
Explore the high seas in style on the Schooner America 2.0, the namesake of the first sailboat to win America's Cup in 1851. This stunning 105-foot sailboat features teak decks, mahogany trimmings, and ample seating for the whole family. The sights you’ll see along the way include a waterside view of Fort Zachary Taylor, the famed Sand Key Lighthouse, Mallory Square, and Sunset Pier. So sit back and feel the warm breeze dance across your skin as you watch the sights of the beautiful waters around Key West. Book your spot today!
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Sunset Sip and Sail with Open Bar and Live Music

53 ratings
2 Hrs.
Have you ever seen Key West at dusk on the open ocean? Just sit back 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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Rise & Reef Snorkeling Trip With Breakfast & Unlimited Mimosas

39 ratings
3 Hrs.
Take an adventure into the depths to explore Florida's best reef on a snorkeling experience you will never forget! The Sandie Cat is Key West's newest and fastest snorkeling catamaran, which means less time wasted and more time for exploring the deep blue sea! Join the crew as they hoist the sail and get you and your family and friends out for a true Key West experience. Enjoy a complimentary breakfast, as well as unlimited mimosas (mango, strawberry & orange) & unlimited draft beer, in this all-inclusive snorkel experience. Reserve your spot today!
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Key West Sunset Snorkel Cruise

60 ratings
3 Hrs.
Treat yourself to an evening of incredible snorkeling, delicious drinks, and groovy melodies on the Miss Valyn Catamaran. A twilight experience unlike any other, this is your opportunity to enjoy the nightlife while having the option to plunge into the depths by Florida's best reef! Take in the fleeting Key West sunset while indulging in an ambiance that only the cat delivers. Enjoy reef snorkeling, draft beer & wine on this snorkeling experience. Book your spot today!
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Morning Half Day Sail, Snorkel, and Kayak Excursion

27 ratings
4.5 Hrs.
Get out early and experience nature at its finest with a half-day island adventure complete with sailing, kayaking, and snorkeling all in one. 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 natural beauty around you. Live the island dream as you set sail in a 65-foot schooner, then kayak through the mangrove forests and snorkel the blue waters. Book today and let your adventure begin!
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Key West Sailing, Kayak, & Dolphin Watching with Breakfast and Lunch

10 ratings
6 Hrs.
This fun-filled Key West tour combines three awesome adventures into one package. Enjoy a day of sailing, snorkeling, and a grand kayak tour through the mysterious mangrove backcountry. An awe-inspiring eco-tour of glorious Key West, you'll embrace nature in all of her glory as you encounter and observe diverse wildlife on land and under the sea. This all-day adventure includes delicious spreads for both breakfast and lunch, as well as an afternoon snack that is sure to please. Book your Key West adventure today!
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Schooner Champagne Sunset Sail

11 ratings
2 Hrs.
Come along on this Champagne Sunset Sail and step into luxury. Sip, relax, and unwind aboard a gorgeous wooden schooner. Enjoy your authentic sailing experience as you cruise the crystalline waters 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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Full Day Sail, Snorkel and Kayak Excursion

12 ratings
6.5 Hrs.
Get out on the water and experience nature at her finest with Full Day Sail, Snorkel, and Kayak Excursion complete with sailing, kayaking, and snorkeling. 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. Let your adventure begin!
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Afternoon Reef Snorkel and Sail

1 rating
3 Hrs.
Immerse yourself in the tropical waters 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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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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Stock Island Wind & Wine Sunset Sail

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2 Hrs.
Climb aboard a 65-foot historic Schooner for a luxurious experience that has been rated one of the top two sunset tours in all of North America by Coastal Living Magazine. Join this unforgettable Wind & Wine Sunset Sail in Stock Island, Florida! Embark on this journey and indulge your senses with a selection of wines and light appetizers that beautifully pair. As the Schooner glides across the water, you will witness the breathtaking spectacle of the sun melting into the horizon, casting vibrant hues of orange and pink across the sky and reflecting its beauty onto the water. This charter offers more than just an opportunity to relax and unwind, it is a chance to connect with fellow passengers, make new friends, and share in the joy of this extraordinary moment. Whether you're a wine enthusiast, a sunset lover, or simply seeking an exceptional experience, this journey promises to exceed your expectations. Book your spot today!
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