The Caribbean - High Season in the Carribean?

Any ideas when airfares to the Carribean get a little less pricey, (or tools which which quickly show airfares across a wide range of dates?) I was looking at airfares to SJU in January, and they are pretty expensive. I suppose I should have realized that would be high season, but now that I know that, I'd like to figure when "high season" starts to end. My dates are pretty flexible, and any time from Jan 1 to to 3/15 should work for me.

Suggestions?

High season is usually December to through April depending on where you are going. Some places have a shoulder season that would be Oct-November and May/June. Any holidays during those months are usually carved out for higher prices.

Cheapest time of year for the Caribbean?

Two words:
Hurricane season

One of the things to consider when going in "high" season whether it is the carribean in the winter or europe in the summer is that fares are more likely to go up than go down the closer you get to departure time.

We bought tickets to go to the Puerto Rico DO, in mid-January, when they were very low priced. ($218+ sfo-sju purchased in May) Tickets are now over $400+ and unless loads have not met expectations I do not expect that they are going to get lower. If they do get lower than what I paid than a refund of the difference will be in order. YMMV

....... (or tools which which quickly show airfares across a wide range of dates?) ......

Suggestions?farecompare.com will show you a wide range of fares over a one year period. If you become a little familiar with the website, by reading the following post on their site you might learn how to find out if there have been spike drops in the past. Others have found that for example fares always seems to drop on the route they are searching for in the last week of September or the first week in December.
05/31/2006 Addition of "Fare Trends". Explained in detail in the document Using Historical Information to Make Better Buying Decisions (PDF) or HTML.

Please continue to follow this thread in the FT Caribbean Forum.
Obscure2k
TravelBuzz Moderator

On the Mexicaribbean side, they call November "Novihambre" - "Novhunger" due to the low season issues. There and in places like the Virgin Islands, they seem very happy to see folks November through December ~15, when the gong rings and high season is tolled in. I've benefitted from some nice fares, accomodation prices and dive operator prices during the Nov ~ mid-Dec lean times.