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I have windows, November and December, then April and May but this is in Florida and I'm on vacation, hence why I choose to have a boat here, however when we do have good days in the UK I'll blag a loan of a Jetski or wakeboard behind a boat if invited.
The British summer is generally good but water temps are never high so a wet suit is always used but then we don't have stinging jellyfish, sharks, stingrays or Gators .
I usually target Memorial Day to have the boat ready (but don't go out until the following weekend to avoid the drunken amateurs that day).
The season usually ends in late September / early October for us. The actual day that I winterize and put away for the year is more dictated by other commitments than weather. That said, I have no desire to be out in the driveway winterizing on a cold, drizzly late-October day, so I'll admit I hedge my bets and put away a little earlier than I probably need to. This year I could have been putting away mid-November and still been nice and warm.
As to the second part of your question: We are usually happy if we get out 8 - 10 times in a summer. (1 "time" = one full day on the water from about 9:00 a.m. until at least 5:00 p.m.)
It's not as much as we'd like, but I know we still do better than some so we take what we can get.
I put ours in in mid April, and we're out in early October before they pull the dam boards on Columbus Day. Of course, living on the lake helps, because I can continue the spring cleaning on the boat while its' on the dock. We would probably stay in until November if the boards weren't getting pulled, but with low water years like this one we knew it was time to get out.