I am sure that if you go to or contact any of the Yacht harbors in Mo Bay or Kingston you will find sail/motor yachts for rent with a crew/chef....I have Bareboated in the Bahamas which is simply renting the sailboat and sailing yourself..Jamaica is not known for bareboating as many of the reefs are very hard to read and navigate. Most of Jamaica is open watre sailing as well and is not as as easy and laid back as inner sea sailing that you willfind in the Bahamas and many of ther other Island Cahins in the Caribbean. For the true sailors out there the open water is where they want to be in a broad reach making wake. I really see no reason to pull into say Fallmouth and tie up next to a bauxite freighter loading red dirt....

Jamaica just is different than many of the Island Chains...I am sure that with a good boat and a good crew they would take you to some very nice spots but Jamaica is not the destination if I sailed or Bareboated again....In the Bahamas running aground on a sandy bottom is much more foregiving than running up on the reef...