Since you live in New York, I would check these two websites for deals to the Caribbean.
I usually do my research on the web and then check with my local travel agency. Most times they will match what I find on the web and often they are cheaper. They have the contacts with the resorts and airlines. Liberty Travel (gogo tours) have great travel packages.
Punta Cana, Dominican Republic have great all-inclusive resorts, beautiful beaches, decent food and a fun place.
I also like the Riviera Maya area in Mexico for all-inclusive resorts. The Palace or the Riu Resorts are very nice.
The most economic time to travel is right now. But it's also hurricane season. September being the most active month for tropical storms.
There are deals out there the first 2 weeks in December. You have to search. Mid January (right after New Years) for about 2 weeks. High season starts Dec 15th to about April 15th. Prices will drop after that (spring sales) Hurricane season June 1 to Nov 30th prices drop some more. This is what I have found and I live in the New York area.
I just booked airfare to St Maarten for $350.00 round trip for November. That's a great price. However, we are flying non-stop mid-week. (cheaper rates mid week)
Good Luck, I hope this answer helps)
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