Ahhh, the jort. After relocating from a major metropolitan area to upstate ny I was surprised to find that people still wear this oft overlooked "fashion staple". Often with thick white socks and off white (from age) sneakers, mullet optional.
My reply is, and has become standard as I grow older and care less what people think - do what you want to do, and wear what makes you feel most comfortable. It is your vacation. I do own a pair of cut off jean shorts that I wear with a white tank and strappy sandals because I like how it looks. I think they would be a little heavy in Jamaica weather.
Personally I like the Jorts with tall white socks and work boot look. Does that cry BEACH or what? Oh, I don't smoke, but I still roll a pack of cigs. up in my white T shirt sleeve. That and a second degree sunburn and I'm on vacation!