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I just got back from my eighth trip to Jamaica.
I've been to Kingston, during the day. I wouldn't want to stay in the city without a well-known and trusted local as a guide. Neighborhoods change quickly from posh to ghetto in a short distance. Plus, way more importantly, Jamaica is electing a new Prime Minister on Dec. 29th. If you were planning on going soon, like next week, I'd wait. There is a long history of political violence on the island often centering in Kingston.
I wouldn't recommend trying to see too many places your first time. Find somewhere you like, relax and chill there for a while. North Coast is nice but busy touristy. South Coast is really nice and less populated. Negril is the party town and you either choose to stay on the 7-Mile Beach or the Cliffs of The West End. I like the West End best...
Remember, if you travel, don't carry ganja with you. There are frequent road blocks and you don't want to have to bribe your way out of trouble, or worse, go to Jamaican prison. You'll be able to get plenty more once you reach your destination...
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