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November it can still be very hot, it starts cooling down in December. Hurricane season is thru the end of November. I think either month will be a nice time to go, with December eliminating hurricane risk. I personally go in November.
If you're into boats that go fast, the first full week of November is the Super Boat International World Championships. Races on 2 or 3 days, plus a Duval Street party and lots to see. That's my week in Key West.
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