I keep my boat up on the shores of Lake Champlain for the winter and sail down the Hudson to get to some actual sailing with steady wind and ocean swell. I do not like even hoisting sails in the capricious winds on the Hudson or for that matter on the lakes. Am sure it's a different story on the Great Lakes where you can get away from land effects. One design boats like Bluejays and Lightnings can be fun on the Hudson for day-sailing. The summer afternoon onshore breeze goes pretty far up, at least to Haverstraw. If you live in Albany there are plenty of places to keep a boat and then just use the river to get to the ocean. If I were a bit closer, would keep the boat down that way to avoid having to travel the Champlain Canal which is novel about once and then just tedious thereafter.
Alberg 35: With a philosophical flourish Cato throws himself upon his sword; I quietly take to the ship.