We always go the first weekend of December. It fits our schedule and lets us "reconnect before we disconnect". I work a second job doing taxes, which helps pay for the trip. We live in Central WI so we like to get away when it is cold, and by the time tax season is over, we are getting warm again, so December fits us best. To us the weather and the water are fine (but like I said, we live in central WI)
The weather in Jamaica varies little through the year, they don't have weather temperature seasons like we do. If you were there and it wasn't warm enough for you it was a fluke. We usually go in November but have been in October a few times, both are hurricane season. We've had a few evenings that were chilly according to what we had expected due to storms but always able to wear swimwear during the day and be on the beach comfortably.
From the FAQ page but you'll find the same info if you do a google search on Jamaica weather:
We will be at CTI in a few days too. We have been going there in April for a long time. The weather is always great. Even with the sometime short showers, it's all good. Not to worry.
If you are out on TI you can look for us. We are known as "April Amigos". You are welcome to join us.
We like mid December for our trip. It starts to get colder here in Ohio then and it's nice to escape from it. Although it is colder in January and February, December (before Christmas) lets us take advantage of the "Low Season" rates but keeps us out of hurricane season (which officially ends November 30). Going in December also helps with having my mother-in-law watch out daughter. It's easier since our daughter is still in school so my MIL doesn't have to be "on duty" 24-7.
We like April but it is hard now that we live far away from all of our family and we have young kids, some in school. The weather in April is great and the price drops so that is nice too. Where we used to live it was still pretty cold in April so it was nice to get away from that. Here it isn't so bad. Sometimes it is nice and sometimes it isn't. Last year we left when it was in the 40s and came home to 70s and tulips blooming.
We went in October once and that was nice too. Again, that's a hard time for us with school and everything. Next year we are going to go in the end of July/beginning of August because that's not a very busy time for us and my mom can watch the kids since she has summer vacation too. I think July/August will probably be our new time to travel until the kids are a lot older.
The down side of April is that lobster is not served. I can't eat it but my husband loves it. There are a lot of other awesome choices during the off season and it doesn't really impact our travel plans, but now he knows what he is missing since we went in Oct last year. Lucky for him we are traveling during lobster season next year.