I did a Hudson trip with my old boat in September of 2015 and can't wait to do another one with this boat this year. I went straight up to Kingston last time, stayed there overnight and then went south for another overnight in Liberty Landing. The only thing that rivaled the scenery were the numbers on my depth finder. I think we're going to try to do 4 nights this time with a stop at either the Culinary Institute or West Point area then continuing the next day further up towards Albany, a third night at either Newburgh or Haverstraw and then a fourth night in Jersey.
Those who haven't done it before should seriously considering going up the east side of Manhattan to Spytun Dyveil and then coming back down along the west side.