I have traveled solo since I was in my teens and early 20s with my first travels being a 3 month camping trip down the coast of Mexico. In my twenties I also traveled to India and many European countries. I didn't get to Jamaica until later in life, but always went solo and loved it. Be sure to stay somewhere secure, always use red plate cabs and the advice that has been given here about having a designated driver for when you want to go out to shows, etc is a good one. I have heard good things about Judy house--and I think you might meet fellow travelers there to hang out with. I have met so many wonderful locals and also a handful of shysters. Use your street smarts and don't let anyone hustle you. Carry a cell phone and have a contact number for someone at Judy House and your driver in case you find yourself in an uncomfortable situation. GO! You will love your adventure. I am so thankful that I traveled as much as I did on my youth--those experiences are with me forever and I treasure the memories! You are full grown--enjoy, explore and learn. And do whatever you need to to make your dad feel more comfortable about it.