Take your time sailing in late season. Don't go far, don't start early, quit early. That takes advantage of the shorter days an limited warm sunlight.
Sail down wind as much as you can, that's the warmest. Sail upwind less, try to plan that in the mid day sun.
Plan for the most protected anchorages at night.
Keep lots and lots of cloths onboard. You don't need fancy gear(but that's fine) but layers of clothing can make all the difference on a boat in the late fall. If you're a skier, you have lots of good cloths for late season sailing. Sailing is pretty sedentary compared to skiing so plan on extra layers. Hats, hoodies that close off your neck, you're from Buffalo so you know what I mean.
The good thing about sailing dressed like this is, you probably won't see anybody.
For overnights, be sure you have lots of layers for berths. You can stay warm if you're dry and have enough blankets/comforters, etc.
Any kind of heat is nice. If your engine is clean, open it up(turned off of course), to the cabin after you motor into an anchorage. It'll warm things up quite a bit.
Cook a chicken if you have an oven(I'm not kidding, but it could be a pizza as well

)
Don't even think about getting wet!
Any kind of heat is appreciated, especially in the morning.
If you want company, it's good the person is into winter recreation. My wife loves sailing in October in Maine. We're snowboarders in the winter.
Did I mention a little heat is nice?