We've had good luck with the end of April/beginning of May. Weather is warm without being too hot and humid and the seas have been calm. Had some rain, but never a full day of it.
Celebrity Century 1/09
Carnival Destiny 10/07
Carnival Destiny 9/06
Monarch of the Seas 3/06
Carnival Inspiration 8/05
Carnival Miracle 4/05
Carnival Inspiration 4/04
Sovereign of the Seas 4/03
We've done a lot in April and May and have always had good weather. June is OK. Late July & August could be rainy as well as a lot of kids. Last week of November and first week of December is a great "price deal" time and weather is OK.
Hurricane season is what you want to make of it - if you go with "it was worth the money" and "we had a great time" attitude, then you will do OK. If you think you get a great deal and then squawk about the seas and the weather, then you should go in the spring. The cruise lines do a great job of avoiding weather but there are times when, well, it just gets rough.
The temperatures aren't that much different between summer and winter for most of the Caribbean, especially for those of us coming from the North Country (Maine). Warm is warm and very greatful. :O)
Actually, a good TA should be able to tell you what time of the year us best for whatever destination you have chosen. You can save money going off season, but I think you can pay a big price weather-wise.
We have taken 4 winter cruises because it is nice to get away from the yucky OH weather for a while.
We have taken one summer cruise--to Alaska. It all depends on what you want. If you want to escape the cold and snow, go in Jan/Feb. If it doesn't matter, then go whenever your schedule permits.
I'm trying to get DH to agree to two cruises a year again so we can do the British Isles/Norwegian fjords and the Mediterranean and also do the Carib in the winter. He's not quite ready to shell out the $$$, but does want to do the summer ones and skip the winter ones. But my mental health needs a sunny break in Jan/Feb, so we are at an impasse. However, the friends who helped me twist his arm to do Alaska are gung ho on our coming with them on the other summer cruises, so I do have hope.
Explorer E. Carib. 1/12/02
Explorer W. Carib. 1/18/03
Summit Alaska cruise/tour 8/3/03
Adventure S. Carib. 2/8/04
Galaxy Panama Canal 2/3/05