The previous advice about insurance is good! Two things I should mention: Caribbean ports are generally not as hot as the Gulf coast areas in the U.S. Expect temperatures around 85-90, and humid, on the islands. The ocean temperature is in the 80's there, so the breeze is pleasant but not cool! I cruised in late Sept. a couple years ago, when there were 3 tropical storms circulating in the Caribbean, but we never saw a single one of them, and the water wasn't even very rough. That's one advantage of a cruise - they can stay away from the hurricanes, and often avoid any "side effects" (such as rough seas), unless of course a hurricane hits the port of embarkation! Hurricane season is why cruise prices are so low in the late summer and fall.