I know ANY TIME is the best time to cruise, but with my work and demands, the busiest time is July through beginning of September when time off is not usually approved, and OT is "required" to meet the needs. I've got my eyes on some Caribbean cruises from September through December, but my only times I've cruised were in July and April/May. 

Just looking for some feedback from veterans on experience and preference on sail dates. Has the weather still been warm and beautiful during typical winter in the northeast? Were the seas rough during hurricane season?