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Try looking at Com-pac Yachts
You might try looking at Com-pac yachts, they are made in the Clearwater area and were designed for the type of sailing around Tampa. Shoal draft, but very seaworthy in a variety of sizes from 16' to 27' and prices from $2500 on up to over $30,000 depending on size and age. I have sailed a com-pac 16 from the Fort DeSoto park ramp all around the Tampa-St Pete area and out around Egmont Key. Pick your weather conditions right and you can go 5-7 miles offshore easily enough, I've sailed the compac 16 in 5' choppy seas at the mouth of the bay with the tide going out and the wind blowing in.
You just have to be careful of the cruise ships and freighters because you're sure not going to outrun them ! I just purchased a compac 23 and look forward to making some longer trips in it.