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Key West Special Occasion Activities, Tours & Attractions

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Dip and Sip Afternoon Snorkel with Open Bar

Dip and Sip Afternoon Snorkel with Open Bar

44 ratings
Duration3 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!
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$46
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Southernmost Sunset Sail with Bar and Hors d’Oeuvres

Southernmost Sunset Sail with Bar and Hors d’Oeuvres

189 ratings
Duration2 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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$74
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Champagne Sunset Catamaran Cruise

Champagne Sunset Catamaran Cruise

94 ratings
Duration1.5 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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$53
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Key West Sunset Dinner Cruise

Key West Sunset Dinner Cruise

270 ratings
Duration2 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.
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$80
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Half-Day Key West Ultimate Sandbar Adventure with Mangrove Kayak Eco Tour

Half-Day Key West Ultimate Sandbar Adventure with Mangrove Kayak Eco Tour

1 rating
Duration6 Hrs.
Enjoy the ultimate combination of adventure, rest, and relaxation on this Half-Day Key West Ultimate Sandbar Adventure with Mangrove Kayak Eco Tour. Cruise out to the Florida Marine Sanctuary for an incredible guided kayak eco tour through the mangrove isles and keep your eyes open wide as you never know which of the over 500 marine species of wildlife you will encounter. Your expert guides will take you to the best spots! After the kayak tour, have lunch on the way to a local secluded sandbar and then when you're all done on the kayak tour, the bar is open!! You will have unlimited access of soft drinks, draft beer, and wine selections. Grab a beverage and explore the secluded sandbar. Each trip will have a master captain and two additional crew members catering to your every need. Leave your stress behind and book this amazing sandbar adventure today!
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$110
per person
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Dolphin Watch Sunset Sail with Premium Wine and Tapas Pairings

Dolphin Watch Sunset Sail with Premium Wine and Tapas Pairings

102 ratings
Duration2.5 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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$85
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Key West Kayak Eco-Tour

Key West Kayak Eco-Tour

16 ratings
Duration2 Hrs.
Join in on this guided Key West Kayak Eco-Tour and paddle at a relaxed pace through the crystal clear water of Key West's backcountry. You will see beautiful seagrass beds and paddle alongside and even through the intricate and enchanting mangrove eco-system. Learn all about the local marine life including tropical fish, birds, sponges, sea stars, and jelly fish. You will even see the occasional shark, ray, or manatee! This is a great option for kayakers ages 6 and up. Get out in nature, book this Key West Kayak Eco-Tour today!
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$55
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Downtown Parasailing Adventure

Downtown Parasailing Adventure

3 ratings
Duration1 Hr.
If you are looking for something exciting to do over downtown Key West, then this is the adventure for you. Parasail the blue skies over Key West's eclectic and colorful downtown and see everything from 300 feet in the air! One of the most extreme and stunning activities around, so take in the scenery, look below for mesmerizing marine wildlife, or simply enjoy the salty ocean air as you soar. So what are you waiting for? Book today!
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$66
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Beach Pass Watersports Package with Beach Chairs and Umbrella

Beach Pass Watersports Package with Beach Chairs and Umbrella

2 ratings
Duration8 Hrs.
Enjoy everything Smathers Beach has to offer with this Beach Pass Watersports Package with Beach Chairs and Umbrella. Capture the magic of Smathers Beach with this all-day Ultimate Beach Pass. This amazing pass offers something for everyone and includes volleyball, paddleboard, windsurfing, kayaking, Hobie Cat Sailboat, beach chair rentals, umbrella rentals, and float rentals. A tremendous value and a great idea for groups, get your Beach Pass and get out on the water today!
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$100
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