I live on St Croix in the USVI....we have the good fortune to be able to sail pretty much all year round,,except for an occasional hurricane its pretty much a sailors heaven....living right on the water is certainly a nice plus,,,but also very expensive...Im about 15 min from the yacht club where I keep my boat right on the beach...the summer highs are in the upper 80s while our winter is the low 80s,,,tough to take but we mamage..lol...the water temp drops below 80s so we pull out the wetsuits...the trade winds are pretty good all year...the norm in the winter is 10-20...summer there are some lulls but not bad at all....but the warm weather all year round is the best,,,,