Definitely allow for time on The Lake. I just did the trip from Hudson to Wilsboro Bay and back in August - seven days total without staying two consecutive nights in one spot. I could have stayed at Wilsboro Bay for a week! For the upper-Hudson end of the trip, assuming you head for the locks out of Kingston or Catskill (Catskill being a bit further north and a decent day-cruise from NYC), expect to get to Lock C5 in one day, C12 (the last lock) the next day. From there, Wilsboro or Burlington can be done the next day in a 28' cruiser (what I have as well). My recommendations to look into on your own would be: Rondout Yacht Basin (if you stay in Kingston), Catskill Marina (if you stay there on the creek); Schuyler Yacht Basin is your only choice at Lock 5 - I didn't love it but it served its purpose; Whitehall Marina vs. Lock 12 Marina (although the restaurant at L12 Marina is terrific); I stayed at Westport Marina after Whitehall because I thought I would need to for distance, but it wasn't necessary and I didn't love it; then Wilsboro Bay Marina which was exceptional with a top-notch restaurant. From Wilsboro you can do lots of exploring, including Burlington. I was told, and found it to be true, that if you don't get at least as far north as Wilsboro, you haven't really experienced The Lake. Please let me know if you have any specific questions about my trip!