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The top boating charters in Caladesi Island

Caladesi Island

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Step aboard Sunny Day Family Charters, a beautifully restored 2007 Andros 26 Tarpon Bay boat (refitted in 2025) based in sunny Clearwater, Florida. 

Sunny Day Family Charters

Experience the ultimate adventure on Fish Fixation LLC, a brand-new 2024 Blazer Bay 2400 Bay Boat, departing from the scenic Tarpon Springs, FL. 

Fish Fixation LLC

Looking for an exciting boating adventure? Wish Upon A Fish Charters is your ticket to an unforgettable day on the water! 

Wish Upon A Fish Charters

Get ready for an unforgettable experience aboard Wet Lines, a luxurious 2019 Misty Harbor S-2685SR Pontoon, cruising from the beautiful shores of Clearwater. 

Private Boat Tour

Welcome to Suncoast Island Adventures, where adventure meets tranquility on the sparkling waters of the Gulf of Mexico. 

Suncoast Island Adventures!

Step aboard Fishful Thinkin Charters, a powerful 36’ Cape Horn Center Console, and get ready for an unforgettable day on the water! 

Fishful Thinkin Charters

Embark on an unforgettable adventure with Olt Bay Adventures, offering a luxury experience aboard a 2023 Skeeter SX230 Bay Boat, based in the beautiful Belleair Bluffs. 

Olt Bay Adventures

Embark on the ultimate Florida adventure with a private, customizable boat tour! 

Wells Saltwater Tours

There is no better way to experience the beauty of Clearwater than by getting on a boat and seeing it from the water. 

Island Time Family Eco Tour/Fishing Charters

Experience the ultimate Clearwater boating adventure aboard this 2019 Sun Tracker Party Barge Pontoon! 

Caladesi Island: 17 boats available

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Caladesi Island: 17 boats available