This is a beautiful area with several 30+ mile long lakes that average 1 to 5 miles in width so you can go a long way, but not feel that you are out range of help if you need it. There are no reefs or rocks for the most part so you don't need to worry too much about navigation skills. Cayuga and Seneca have many areas below cliffs that are not accessible except by water for nice private picnics.
Unfortunately the season is VERY short if you have an aversion to cold water. The best sailing is mid-July to mid-October. Sailing in the fall is especially rewarding with the foliage in full bloom, warm constant breezes, warmer water (high 60's), and only a few fisherman sharing the the lake - no summer visitors or $%^ jet skis.
Oh yeah - we are a recognized appelation' for wines. That means great wines and about a zillion wineries to choose from. Red Zeppelin or Red Cat are winners for a fun day of sailing without any wine-snobbery.
I love where I live - come up and visit sometime.
http://www.visitfingerlakes.com/
