Booking a trip to the Caribbean seems simple enough. The islands are right around the corner. Most don't have visa requirements. All you need to do is jump on a plane, hail a taxi, beach yourself on a patch of sand, and wait for people to start fanning you.
But as you're happily, blissfully letting your guard down, you have to be prepared for a totally foreign experience. Even in American territories like Puerto Rico and the Virgin Islands, the rules are different when you get to the Caribbean. First-time visitors naturally make a lot of mistakes, and even when you've been going for as many years as I have, you keep finding more to make. In hopes that you don't, I'll share with you the stuff you need to do (and not do) to make the most of your trip.
Assuming everyone speaks English
Even if you're not so big on stuff like "history," you should know that the Caribbean was colonized by the Spanish, French, English, Dutch, and a few other countries over the better part of the past millennium. Accordingly, people do not speak the same language in every country, and the dialects of the languages they speak are completely different.