Sailing is best described as "terror at 7 miles per hour," meaning while you are in constant danger and must remain vigilant, it is kinda sedentary.

If it gets really cold (and even in Florida, it gets cold), I have gear for my extremities: Going from the outside in on my feet, I have a pair of oversized surf socks. These are water permeable, so under those, I have a pair of waterproof socks from SealSkinz. The SealSkinz are not insulated, so I have a pair of shortie socks made from Menlo wool (wool stays warm when wet.)

For my hands, I have a pair of waterproof ski gloves with fleece inserts. To me, gloves are useless since your fingers are always cold and you have to take them off for any fine work, anyway. Mittens make much more sense.

My cold weather hat is very special. My mother's pastor spun the wool from sheep found in the ghost town of Shaniko. It is possible that is the oldest strain of sheep in Oregon. Once spun, my mother knitted the hat according to my specifications. That's a damn special hat. I just might have to be buried in it.