From where you are, I'd be totally comfortable turning the AIS back on, but it's the Skipper's call. We didn't find the traffic to be that congested in the Yucatan Channel, but since we were so close to Cuba (about 5 miles offshore) and we were in the Traffic Separation Lane, we preferred to have the AIS on at that point. Once we rounded the Cape, we hugged the shore, well, about 10 miles out, heading East until we were crossing the Gulf Stream on a more direct crossing.
Once you get around the corner, you will have the waves out of the North, today 2', 4 seconds, building to 4', 4 seconds tomorrow, then 4' 5 seconds on Sunday, all out of the North. . . . . Forecast . . . .
Once they drop you off, do they plan on staying in Key West for awhile, or heading North? Route? East via Hawks Channel off the Keys, or farther offshore, or NE across the Gulf to Fort Myers and Caloosahatchee Canal?
If they come through the Canal, they can tie to the dock if you give us a day or so notice.
Safe travels!