We boat out of Stony Point, on the Hudson.
We have done the trip south to the Inner Harbor.
We have also gone north, through Lake Champlain, up to the St. Lawrence, past the 1000 islands and over to Toronto. We came back across the lake to Oswego, then east on the Erie canal.
Coming up from the Chesapeake, we stopped at Cape May, and stayed at Schooner Island Marina. It is a clean, nice place, low fuel prices and close to groceries, restaurants and the beach.
I recommend fueling up in either Manasquan or Belmar before getting into the Hudson where fuel prices are much higher.
Navigating the Hudson is very easy, for the most part the water is deep enough, and the channel is well marked.
The best place to anchor is off the beach on the north side of Croton Point. We like Bowline pond across the river from Croton, but you need local knowledge to get in. Someone from this forum will be able to guide you in, if you desire. Fuel will be available at Haverstraw marina (Tarrytown marina also has fuel, but they are always much more expensive). From Haverstraw, a nice stop is at Shadows Marina or Hyde Park marina, and then a walk across the Hudson on the Walkway over the Hudson.
Kingson, on Rondout Creek is always a good stop.
Navigation gets a little trickier north of Kingston, but if you stay in the well marked channel you'll have no problems.
There are a few marinas in Albany, then you're into the canal. A number of towns provide free tie-up along their bulkheads, and most of the locks have places to tie up for the night.
Lake Champlain is beautiful, plan on spending a few days enjoying it.
We went from Champlain to Sorel, and stayed at the marina right where you come out onto the St. Lawrence. You will probably be coming the other way, which is smart, as you'll have the current with you.