In a state with at least 4500 islands (and you can triple that statistic if you include tiny ones under 10 acres in size) you need a lot of boats. And if you don't have a boat (I'm workin' on it) then you need a lot of Captains. Fortunately for us all, there's no shortage of have-craft-will-chauffeur Captains out there plying their trade.
One of my closest Captainly allies is Captain George on Anna Maria Island, who will for a pittance shuttle your ass wherever you want to go. Even if you don't really want to go anywhere. Even if you just wanna be dropped off on Beer Can Island for awhile to go frolicking nude in the mangroves with a bottle of Kraken and a bag of limes. His boat, the Mystic Dolphin also comes equipped with a CD player that plays both kinds of music - Jimmy Buffett and.... Jimmy Buffett.
Call the man: 941.778.2761. And tell him I sent you by!