Caribbean in October

December through April delivers perfect weather and peak prices. Hotels double their rates, flights cost 40% more, and popular beaches fill up by 10am. But the trade winds keep things comfortable, and you'll dodge hurricanes completely. May and November offer sweet spots — fewer crowds, decent weather, better deals. Hurricane season runs June through November, peaking in September. Don't let it scare you off entirely; many storms miss the islands, and you'll find incredible deals. Just buy travel insurance and stay flexible. Rainy season doesn't mean constant downpours — more like afternoon showers that cool things down. Carnival seasons vary by island: Trinidad in February, Barbados in July, Jamaica year-round but biggest in April.