There are many places to sail in this area if you have your own boat. I don't know of any rental/charter opportunities nearby. St.Peteresberg has several charter companies and individuals that will bareboat or take people out for day charters. The Bahamas are the nearest that have bareboat charters and the waters are stunning. We use to winter at Man-O-war key and cruise in the Abacos.
Nearby we have Lake Harris, Lake Dora, Lake Eustice, Lake Wier, and On the St.Johns river Lake George. Lake George is the largest with Silver Glenn spring a very attractive overnight for shallow draft vessels. Lake Harris is also Large. Lake Eustice has a very active one design sailing club.
We have a small Cat Boat called a Sun Cat. A very unique mast hinge and with a block and tackle makes stepping the mast very simple and easy from the cockpit. Secondly the main sail stays bent on all the time. The whole point is that the boat can go from trailer to sailing in about 15 minutes. We tow the boat all over central Florida from the nearby lakes and coast to coast. It's a shallow draft centerboard boat very suitable for our shallower waters on either coast and the nearby lakes.
Google WCTSS web site. You will find many really cool places to sail to. West Coast Trailer Sailors (WCTSS).
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