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Staff Picks

Who has the best job in the entire world? Ask Lisa, Jen, and Thomas at CoolKeyWest.com: “We do!” As some of the hardest-working vacation specialists in Key West—which means A LOT of waverunner tours and sunset cruises!—no one knows Key West vacation fun like they do. When it comes to what makes Key West great, take it from these three: “YOU do!”

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Special
Offer

Key West Split Fishing Charters

With Key West Split Fishing Charters the overall cost of the charter is split between several people in order to reduce the cost for all.

Times: 8:00AM Duration: 4 or 6 hours Activity Level: Moderate
$350
$165
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Special
Offer

Original Island Jet Ski Tour

On our Key West Island Jet Ski Tours you jump on one of our Yamaha Waverunners and cruise around the island on a 28 mile, 90 mins guided jet ski tour.

Times: 10:00AM, 12:00PM, 2:00PM, 4:00PM, 6:00PM Duration: 90 mins (approx.) Activity Level: Moderate
$150
$129
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Backcountry Safari Key West

Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness.

Times: 8:30AM Duration: 6.5 hours (approx.) Activity Level: Moderate
Best Rate
$120
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Wind & Wine Key West Sunset Sail

The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running. See the sunset on a beautiful 65ft sailing boat.

Times: 4:30PM Duration: 2 hours (approx.) Activity Level: Easy
Best Rate
$85
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Call (855) 274-1023 to speak with an Island Specialist

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