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Montego Bay, take a tour!  Do not go into the downtown shopping area.  If you do, you will be hounded to death by the locals trying to sell you something, or simply begging.  If you wish to do some shopping there, a duty free shopping area is located right next to the pier.  In Grand Cayman, I highly recommend Captain Marvin's Stingray City tour (about half the cost of a similar tour booked through the cruise line).  Do not plan to do any shopping here; prices are staggering!  In Coz, I recommend Chankanaab Park and of course, Carlos & Charlies.  Have fun!