I commuted from the TCI's to Cayman is 2006 with a stop over in Ocho Rios for
fuel, and the
crew wanted a cheese burger in paradise, I stayed with the vessel.
I have had no bad experiences with Jamaica but didn't get a good feeling in my gut both times I've been there. Both times have been just day stops and someone was alway on board.
Cayman does not have much for
anchorages, but there are over 150
mooring balls throughout the three islands. They are not intended for overnight or long term use, but I have not had any issues, other than some divemaster beaking at me one morning after I dinghied in to RENT
tanks from him, about spending the night on one. I asked him if he preferred I rake my
anchor across the
coral instead. Anyway, you will need to check in and out on the West side of the island at the down town
water front. It can be quite rocky and rolly at times because of
tender traffic from the
cruise ships. It's nice to move a little North along seven mile beach and drop a hook if front of the Westin or Ritz hotels.
Depending on your
draft 6' or less, you can get into North Sound and find anchorage in Governors harbour, which is not to bad, and if you go further in to Lime Tree bay, you are walking distance to a Cost-U-Less and some good restaurants.
Hope this helps
Cheers