re: Jamaica. Is it safe to leave the resort?

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Nothing like standing in line with the rest of the cattle at the resort waiting to pile hot dogs on your plate. To each their own.

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Road food is the best. In the Bahamas the local vendor stands had some great food, the restaurants near the beach all catered to tourists.
In Cozumel we traveled to the other side of the island past "the mexican target" to this little cafe. They didn't even have power. Guy was bringing lobsters and fish straight out the water to the grill.
Cheap and much fresher than the tourist restaurants. I always like to rent a scooter or a car.
Only bad (really not bad) experience,was I paid 20 for ganja in Nassau and the guy gave me wadded up paper in a bag. I felt played. lol

Other than that and all the trinket peddlers it wasn't bad.
Mexico, Bahamas, Jamacia Honduras all have similar things around the tourist areas. People know that they can hustle tourist.
Hell New Orleans has a lot of people that hustle tourist, the riverfront is the worst. (Were you got dem shoes at)