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Best time to visit Jamaica The weather in Jamaica is generally sunny all year round, and the weather is warm during the peak tourist season, mid-December to mid-March. You can also visit Jamaica in the shoulder season, from mid-April to May and November to mid-December. During this time, hotels and rates are much cheaper, and the island is less crowded. If you want to avoid the summer crowds, visit during the shoulder season.During the wettest months, October and November have the highest rainfall. June and July are driest months, while July and August are hot and humid. However, you can still enjoy warm weather in Jamaica even during the rainy months, as the island is rainier during these months. Rain is most common during November and October, but the weather can still be pleasant in October. Although October is the wettest month of the year, it can last only a few minutes or even hours.Early fall is the worst time to visit Jamaica, with early fall lands within hurricane season. While the summer months are generally dry, August and October are more likely to experience damaging tropical storms. Fortunately, these months do not see as many hurricanes as the other seasons, so you can enjoy cheap rates and warm temperatures. If you are planning a trip during these months, you should also look into travel insurance to avoid cancellations and costly airline tickets.