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Being in Jamaica without some of my personal music is out of the question for me. If I am poolside, I always ask if others are around if it is a problem. Never had a problem so far but if I would....earphones...never leave home without them!! Relax and enjoy the sounds of sweet reggae or whatever your preference.
You can never beat your own selection of music, especially when your on vacation.
I bring ear buds for the beach and speakers for the room/patio area.
I always bring the iPod and some little speakers. I can't be in Jamaica without my roots reggae. I even bring them down to the beach. I used to be worried that it would bother others and always do the courteous thing and ask anyone that's sitting near us.
I would always be worried I was bothering someone else. I would walk around our table and chairs to try to judge if it's too loud or not. I've never once been asked to turn it down much less off. (there just little speakers, it's not like a Marshall stack) In fact, most times I ask, I hear a "no problem.....turn it up!" You'd be surprised how the sound dissipates in the tropical breezes. You can't hear it after you get about 10' away or so.
Bring the tunes!