If there is a sailor's paradise existing, then it's the Caribbean Islands. They offer ideal conditions for sailing for almost the whole year, the climate is tropical and subtropical.
The sun is shining almost every day and the temperatures are enjoyable high. From May to November there may be heavy rainfall. Depending on the geographical location, there are climatic differences: in the northern Caribbean, e.g. on the Bahamas, the climate is very mild and pleasant. In the winter period, when average temperature falls to 20°, the water is often warmer than the air. The climate on the Greater Antilles is a bit wetter due to the constant wind. The Lesser Antilles, the "leeward islands", are under the influence of the northeast trade winds, which bring moist air with short, violent rain. The "leeward islands" in the south have a much drier climate. Although the Caribbean islands are considered as a year-round region for sailing, you should take into account the period of hurricanes that occur from June to December.
Especially in August and September, there are more and more violent storms.
Air and water temperatures at a glance (eg Antigua):
