We live in the area and very seldom go out more than a few miles out into the nothingness. We have a TI all super rigged with massive sails and outboards, yet I'm pretty sure I have never been more than 5 miles out (in the Sarasota area anyway). We do a lot of 50-60 milers around the area but tend to stay in the intercoastals and near shore. It's really hard to comprehend just how massive Tampa and Sarasota bays are, and just how dangerous they are (the two most dangerous areas on the gulf). Even little Sarasota bay when the wind kicks up gets 4-5 ft washing machine chop where even in our heavily modded for offshore TI we are in great fear. Personally I'm pretty sure you will love the area I'm pretty sure there is more to do here than almost any other place on the planet with your Island, I'm pretty sure we have the highest concentration of Island boats anywhere in this area, and we all have a blast all year round. If your going for the big gaming fish, take a charter out, or better yet just drive down to Islamarada and jump on a charter down there (probably the big game fish capital, and only 5 hrs drive away). Hope you like good fresh seafood, it's the norm down here in restaurants. Good luck Bob
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