I spent a week in Jamaica three years ago. Stayed at the resort Gran Bahia Principe, and it was a very nice, 5 star facility. It was relaxing, but the fact that everyone at the resort pesters you to buy weed from them, got old fast. You can't even go to the pool without being asked 2 or 3 times.
Safety wise, we (group of 7 guys) didn't have any problems, however while we were there one of the security guards that mans the enterance was shot. We didn't hear about it till 3 days after when our room service guy asked us if we heard the shots.
We ventured into ocho rios to hit up a club called Margaretaville, and while the club was safe inside, the outside was sketch as fuck.
After all is said and done, I would go back. But that is because I perfer to smoke over drinking, and with any other island nation, like cuba, it's much more risky to blaze.
As for the prices of weed, like everywhere, you'll get a better deal if you buy larger quantities. Don't pay more then $200 for a Quarter Pound.
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