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Re: Charter in Tampa, St Pete, Ft Meyers, Marco?
I recently chartered with Sailing Florida, and did a daysail with Southwest Florida last winter.
I'd recommend both of them. The cruising grounds in the Gasparilla Sound (Southwest) are nicer, as most of Tampa Bay is too shallow, and there is only one really nice anchorage. My memory is that the boats at Sailing Florida are both newer and less expensive. The staff at both are quite good, and the actual marina at both places are very nice.
I don't think you would really go wrong with either.