Negril in December

December through April is peak season for good reason — the weather's perfect, trade winds keep things comfortable, and rain stays away. But you'll pay for it. Hotels double their rates, and Seven Mile Beach gets packed with cruise ship crowds. Here's the sweet spot: late November or early May. Weather's still gorgeous, but prices drop and the beaches clear out. Hurricane season runs June through November, but don't let that scare you off completely. September and October see the most storms, but July and August can be brilliant — hot and humid, yes, but also empty and cheap. The rain usually comes in quick afternoon bursts that cool everything down. Plus, this is mango season, when the fruit falls off trees and into your rum punch. Just keep an eye on the weather and have flexible travel insurance. December brings the most tourists but also the best party scene. New Year's Eve at Rick's Cafe is legendary, but book everything months ahead.