The best is always relative, and that definitely applies to the best time of year to visit the Caribbean! There is sand and sun all year round and winter temperatures do not change much from summer. The best time will depend on where in the Caribbean one is visiting, where one is travelling from, and what one is looking to do. Having lived and worked in the Caribbean for over 22 years I can say that only you can decide when is the best time for you!
Each region of the Caribbean has special festivals at different times. Antigua and Nevis do carnivals the first week in July, St. Kitts is the week between Christmas and New Years. Trinidad is just before Lent. Then there are various music festivals, sailing weeks and parties scattered throughout the region and the year. There is always a party somewhere in the Caribbean.
If one is travelling from the northern regions of the world, winter may be best. The Caribbean is a good area to go to escape those cold arctic winds and enjoy some warm sunshine. The winter temperature averages just over 79 F on the smaller islands of the Eastern Caribbean and marginally warmer in the larger countries. Showers are light and usually in the late evening or early mornings, when most people won’t be out anyway.
Those from more southern places should consider the Caribbean during the summer. Unlike the southern United States or Mediterranean, much of the Caribbean does not under go temperature extremes. The sun may pass directly over head, so use sun screen, but the temperature in many places only averages 83 F in July/August! If it does feel too hot, take a dip in the sea! The waters in the summer are at their best with visibility for diving some days at 200 feet! In winter, when it is 3 degrees cooler, visibility may only be 100 feet, still not bad.
Everyone does not always visit the Caribbean for vacation, some go to visit families or for conferences. In that case, summer rates for flights and hotels are cheaper, so one can stay longer, “island hop” or do more activities. For any discount traveller, May through September is the time to visit the Caribbean. Many worry about storms, so go in May through July as there are few hurricanes before August and most are further north, hitting Florida and the South-eastern United States! In this day with modern weather satellites and communications, hurricanes are easily avoided.
The Caribbean is always a wonderful place to visit. Choosing the time that is best is virtually impossible. Check with what is happening in your life, check out what is happening in the Caribbean (Either through the Internet or a travel agent), check the prices, and the check into the Caribbean at the best time for you!