David, if you plan to go in Big Sarasota Pass there has been recent shoaling reported. It's almost a local knowledge pass at best. Kinda screwy the way in winds in close to shore and makes the turn to starboard. I suggest that you call TowBoat/US or SeaTow for info.
Marina Jack's is a good place. There is a mooring field for about $20 a night. They are limited, so call ahead. You can walk to the restaurants in town from there, or the one at Marina Jack's is good.
Yes that looks like what is building to be an anvil shaped cloud. They get so tall that the winds aloft can be blowing a different direction, and blow the tops in a different direction or speed.
It is kind of touchy getting into Marina Jack's from the pass. You have to get to the GICW and go a little north, then turn around the point of a shoal to starboard. To me the markers are a little tricky at that intersection. Take your time, and figure them out. Gold triangle and squares are GICW.
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