Key West Luxury Activities, Tours & Attractions

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Jun 14 - Jun 20
Barefoot-Billy-s-Seabreeze-Dolphin-and-Snorkel-Tour

Seabreeze Dolphin & Snorkel Tour

18 ratings
3.5 Hrs.
Be on the lookout for Key West’s magnificent dolphins while cruising the crystal clear backcountry waters of the Gulf of Mexico. On this family-friendly outing filled with amenities, observe dolphins and other Key West wildlife mingling in their natural habitat among deserted tropical islands. Don't forget to dive in and snorkel Key West's warm, gentle water to see all the ocean has to offer with a Seabreeze Dolphin & Snorkel Tour. Book today!
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Sunset-Dinner-Cruise-by-Sunset-Watersports

Key West Sunset Dinner Cruise

289 ratings
2 Hrs.
If you are looking to make memories on a glorious Key West sunset as you dine and enjoy drinks with your loved ones, then this is the perfect cruise for you. This Key West Sunset Dinner Cruise allows you to have it all. Experience a delectable dinner and drinks out at sea with a friendly crew and dine on tropical-inspired featured dishes like Roast Pork with heavenly Cuban Bread followed by fried plantains. Your meal is prepared fresh on board and your catamaran features a fully stocked bar and comfortable seating in a climate-controlled cabin. So, get out on the water and dine, drink, and dance away the day on this classic Key West Sunset Dinner Cruise. Reserve your spot today!
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Booked 2 times in last 48 hrs
Land-s-End-Sunset-Sail-with-Hors-d-Oeuvres-by-Sebago-Watersports

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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Key-West-Sunset-Sail-on-America-2-0-by-Classic-Harbor-Line

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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Barefoot-Billy-s-Seabreeze-Sunset-Harbor-Cruise

Seabreeze Sunset Harbor Cruise with Wine and Beer

18 ratings
2 Hrs.
Escape the hustle and bustle and experience a breathtaking Key West sunset with a Seabreeze Sunset Harbor Cruise. Your journey takes you away from commonly charted boat paths to unobstructed views and miles of turquoise waters, while snacking on delicious sushi and snacks. Travel to where the Gulf meets the Atlantic and on to the Southernmost Point of the United States. For an intimate and romantic evening that is sure to help you unwind, book a Sunset Harbor Cruise and toast to life!
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Wind-and-Wine-Sunset-Sail-with-Danger-Charters

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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Sunset-Sip-and-Sail-with-Live-Music-by-Sunset-Watersports

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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Schooner-Champagne-Sunset-Sail

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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Private-Harbor-Day-Sail-Aboard-the-High-Tide

Private Harbor Day Sail Aboard the High Tide

2 ratings
1.5 Hrs.
Cruise the scenic waters 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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Ultimate-Adventure-Key-West

Ultimate Adventure H2.0

2 ratings
3.5 Hrs.
Embark on an all day water excursion that includes unlimited water sports for you and your whole crew with this Ultimate Key West Adventure. Enjoy complimentary snacks and drinks from the deck of a spacious 65-foot catamaran as you cruise the Atlantic for a truly incredible experience. Next, journey into the Gulf of Mexico where you will enjoy an afternoon of banana boat rides, jet skiing, parasailing, and playing on an epic, brand new 3,500 square foot water park. Prepare yourself for good times, food, and fun on this ultimate water sports adventure cruise! Book yours now!
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Private-Snorkel-and-sunset-Sail-with-Sunset-Sail-Key-West

Private Snorkel and Sunset Sail Excursion

1 rating
4 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 sailboat 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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Private-Chill-Out-Lily-Pad-Sail-with-Sunset-Sail-Key-West

Private Chill Out Lily-Pad Sail - Up to Six Guests

2 ratings
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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Sunset-Sail-Aboard-the-Historic-When-and-If

Sunset Sail Aboard the Historic When and If

20 ratings
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.
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Private-Key-West-Morning-Boat-Charter-for-up-to-6-guests

Private Key West 3-Hour Boat Charter

5 ratings
3 Hrs.
Climb aboard for a day of ultimate relaxation on this Private Key West Morning Boat Charter. Get ready to cruise away on a day to remember where you can do it all. Choose from any or all activities including snorkeling, kayaking, paddleboarding, guided ecotours, sandbar trips, family fishing, or just cruising and sightseeing. Totally private and customizable! It’s your day and it can be designed around you and your interests. With no set schedule to adhere to, you may spend as much time doing each activity as you like, just let your Captain know and he will try to make it happen.
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Windjammer-Schooner-Day-Sail

Windjammer Schooner Day Sail

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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. 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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Windjammer-Schooner-Sunset-Sail

Windjammer Champagne Sunset Sail

1 rating
2 Hrs.
Spend a romantic evening aboard an authentic wooden schooner on this Windjammer Schooner Sunset Sail. 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 2 hour pleasure cruise.
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