We spent many years travelling to Jamaica, and have been then well over 20 times. I used to think it was friendly and laid-back until we started sailing down island in what I consider the "true" Caribbean. Because of that, I tend to think of Jamaica as a hurried place where "tourists" are put up with, but not really accepted.
For the last 5 years, we have been spending our time on a sailboat, typically 3 times a year, 2-3 weeks at a time. We sail to small islands, away from the resorts and the tourists, and meet the real natives. It's amazing when you drop anchor off a small island, dinghy ashore, and find a small local bar. Beer and drinks for 50 cents, and many times having them bought for you by locals. We've made a number of good friends down island over the years, a few who have come up to Montreal and stayed with us.
We should get everyone together and do a Webmaster Charter down in the British Virgin Islands or in St. Vincent and the Grenadines. I can guarantee you an amazing time.
BTW, here is the boat we just ordered down at the Miami Boat Show over the weekend.
A cutter-rigged Hylas 54 raised deck, center cockpit 
-- Danny