Den,
Tomorrow does look a bit marginal. Under the influence of a High, just after that front went thru, you'll have some northerly wind flow that could make it a tad rough. Friday seems like a much better choice, especially if you want a good ride for your passengers.
I've spend a ton of time diving on Looe Key (about the half way point) and running up and down that area in small (~25') boats, but when the wind picks up it can get sporty.
Checked the NWS digital wx and shows 15mph winds and 2 ft seas for Thursday. Friday looks much better, but prudent to check again later today, it might lay down a bit. The aviation wind charts show the same.
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Seevee
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