honestly dude... I would pass on Jamaica, I've been there like 10 times, never seen a wave worth surfing. The areas around Kingston have the best surf, If you do end up going. But those areas are also the most ghetto and non hospitable to tourists. Look up Jamnesia Surf Camp, that would be your best bet in that area. Really though... If your going in the summer, hit up central america. And if your going in the fall or winter, hit up Puerto Rico. There is nothing worse than going on a 'surf trip' and not scoring any surf, trust me...
I'm sad to say, i'm on my way.... yeah, man. jamaica is kinda expensive and indeed hostile to tourists unless you know someone who lives there. cheaper and way friendlier (and with some awesome surf) would be guatemala and panama near costa rica (costa rica itself is getting over-used by americans and it has affected the economy, but it is still awesome)....with tourism down all over, a lot of those places are willing to cut some great deals on hotels and car rental. have a blast
Been there once... I'll never go back. Surf is way too inconsistent to be a reliable surf trip destination. Nothing but hassles and dirty looks everywhere I went that wasn't a tourist spot. Even the little kids would give you the finger when you drive by. Better waves and friendlier people elsewhere.