I find that it is possible to sail anytime during the year except for those times when the water and air temperature falls below the level where I can use my hands. Frostbiting during the winter start off by getting into the boat. Hands go pretty much numb. Feeling is lost, then dexterity. Eventually by forcing my hands to operate the boat, they begin to warm up - but its quite painful getting the blood into the fingers. Eventually after a few races, the blood returns to the hands and they seem to work fine. They are beet red and even warm to the touch in spite of holding onto an ice covered main sheet.
Last year I said the heck with this and trailered some boats to Sarasota Florida for several months during the winter.
I investigate the prospects and found that a full membership and boat storage costs at the Sarasota Sailing Squadron was quite reasonable. We drove down with three boats on the trusty SPOT van and deposited them at SSS. I left the van with Chris and Cassie Gorton who were generous enough to store and look after it while we were not there, and to drop it off at the airport prior to arriving each time we arrived.
Chris and Cassie went out of their way to bring us to the local hole in the wall restaurants. I found Sarasota to be a really nice community - an anomaly in Florida.
We flew down every second or third weekend last winter to sail around in the warm waters of Sarasota Bay, spending a total of about 20 days. We sailed in shorts and t shirts, practising in Albacores, and racing with [slaughtering] the SSS Sunday series Portsmouth handicap fleet. We had great breeze every day we were there - only losing one day on the water to threatening thunderstorms. With five boats, Sarasota Sailing Squadron has a growing fleet of Albacores. It seemed like there were always people who wanted to go sailing.
Airfare to Sarasota is running around 200 for a round trip. Sarasota airport [SRQ] is about a 15-minute drive from SSS. Accommodations run from about 75/night on the island and less in town. Camping is permitted on club grounds. Showers are available.
The last week end we spent in Sarasota was for Albacore Midwinters. What a great way to spend the winter.
I plan on driving down again this winter in December.