I have gone to Negril and Montego Bay alone many times and I'm a woman. Can't tell you much about Ocho Rios. I've met some wonderful people and just like at home -- just keep your wits about you. Going out at night is absolutely safe -- I do it all the time. Margaretiville is not my kind of spot -- too touristy but, having said that and your being solo, this might be the place to really meet some people. Also, the Rockhouse on the cliffs, The Jungle, Alfreds and Roots Bamboo Beach Bar. If you really want to get to know the Jamaican culture and make some Jamaican friends, strike up a conversation about the politics and the challenges Jamaicans face. Most of all, have respect, if you're asked to purchase something and you don't want it, say no thank-you but, please don't just ignore the seller. Jamaicans are very proud people. Have a wonderful trip.
Respect.
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