Description: when is the best time to go to jamaica The tropical island receives a heavy amount of rainfall throughout the year. Temperatures usually range from the low to mid-80s. The wettest months are November and October. Rainfall is heaviest on the eastern coast, but it eases up by late November and early December. These months are the most affordable times to travel to Jamaica.If you are staying in an all-inclusive resort in Jamaica, you will want to book in advance to get the best rate. Some large all-inclusives shut down restaurants in low seasons because they're competing for business. You'll also want to check reviews of the property before making your booking. Finally, don't forget to purchase travel insurance to protect yourself against unexpected expenses. You'll want to book early and avoid peak season crowds.