There are three factors to consider when choosing your Caribbean holiday: weather, cost and crowds. The weather in the Caribbean is generally best – namely driest, with low humidity and pleasantly cool nights – December through to April. Summer and autumn are stickier, a few degrees warmer and wetter: showers and short, heavy downpours are common, prolonged spells of constant rain less so. June to November is also the official hurricane season.
Statistically, September, followed by October, are the months you’re most likely to encounter a major storm such as Hurricane Matthew, which caused devastation in parts of the region, including Haiti, in October 2016. However, even in these months the odds are slim. It partly depends on which island you go to, as some are more hurricane-prone than others.
In terms of cost, mid-December to mid / late April is peak season in the Caribbean, and hotel (and villa) rates are 20-50 per cent higher then than the rest of the year. For travel during any school holiday period, you’ll pay a premium for flights.
As for crowds, hotels are fullest and the beaches most crowded in the peak winter months, especially Christmas/New Year, February and Easter. September and October are the quietest months, when some hotels and restaurants close, and bars can be near empty.
Taking into account the weather, cost and crowds, May is an ideal month to visit. The weather then is often almost as good as in the peak winter months, but accommodation costs significantly less. For similar reasons, the first half of December is also a good time to travel. If you’re tied to the school holidays and intent on keeping costs down, consider travelling over May half term, when flights can work out cheaper than other school holiday periods. If you want to go in the school summer holidays, note that fares tend to drop in late August.
