I do t believe you can legally.
Yes. We saw a man getting his stuff all hooked up and ready to go just as we were leaving.
I didn't see anyone doing it when I was there.
In all the years I have gone to Key West, I have never seen anyone parasailing off Higgs Beach. They parasail off Smathers Beach and on the golf side of the island.
You can book a parasailing trip at one of the booths or online
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