US Citizens are slowly beginning to be allowed back into Cuba. You have to go as a group tour, with art, culture or religious purposes. Certain companies are doing it as escorted supervised tours. I don't know much about travel from Jamaica though.
It is very easily done from Canada and sure it is even easier from Jamaica! When flying from Canada all you have to do is ask immigration not to stamp your passport! Not that I have ever done this or anything else that is prohibited by law!
Jamaica is an island country situated in the Caribbean Sea. It is very pleasant place with the nature beauty.
I like the cold places just like Jamaica and Eilat. There are various places available in Israel, which are tourist attraction and one of them is Red Sea of Eilat, one can enjoy the beaches and awesome Eilat weather here.