The most popular time to visit Jamaica is between mid-December and mid-April, when the temperatures are pleasantly warm and there is less humidity. June until October, meanwhile, is considered rainy season, when days can be punctuated by short, sharp showers. Occasional heavy rainfall can also happen at any time of year. The Caribbean is susceptible to hurricanes and hurricane season officially runs from the beginning of June to the end of October. On average, Jamaica is hit only once per decade. The season is at its height in August and September. You can expect higher temperatures and humidity at these times, too.