We push our limits as much as possible.
Our Marina closes on Nov 1. We launch in Mid April so it is a 6-1/2 Month season. That's not bad for midwest.
After Nov 1, I sail with a buddy on a 21-footer on a small inland lake. He is trailerable and the marina lets him haul out whenever he likes. The biggest issue is ice on the ramps. A little ice on the lake does not hurt but a solid freeze would be bad. Snow on the ground does not stop us.

We are going out on Saturday.
During the holiday season we drive down the JAX to visit Family and I bring along our Sunfish, than we go back in March for one last visit and Sunfish Sail.
Before you know it, It's time to do spring boat work.
And you can also throw in a visit to Annapolis or two and sail on a buddies boat.
There is always a way....