Day one - GW to Kingston. Lots of things to see and do in Kingston. These guys can fill you in.
Day two Kingston to the Troy Lock (approx. 3 hr run at 19 kts) and then up into the Champlain Canal to Schuylerville Yacht Basin (another 3 or 4 hours due to locks and no wake - reservations highly suggested). August is Track season in Saratoga which is a 1/2 hour taxi ride (or rental car) from Schuylerville. Also worth seeing is the Saratoga Battlefield which is walking distance from the river and is worth a visit. Downtown Saratoga is very nice.
Next day Schuylerville to Whitehall (End of Champlain Canal - could be 4-5 hours).
Here you have a choice to make. Stay in Whitehall for the night or try to push it up through the narrows of the lake to Port Henry, NY or Addison, VT. There is not a whole lot in between so a lot of folks break up the canal into two days and stay in Whitehall overnight. There is a museum there (Whitehall is the birthplace of the US Navy). Go to the Finch an Chubb Restaurant. It's worth it.
Day four. Get an early start and get through the narrows into the lower broad lake. Option to anchor and visit Ft. Ticonderoga along the way. A good stop is the Basin Harbor Club. These guys know how to pamper a tired crew. You can pick up a mooring at the Basin Harbor Club in Vergennes, Vermont (make reservations). Stay there for at least lunch and go visit the Lake Champlain Maritime Museum which is an easy walk from the club. Give yourself at least a few hours to see the museum.
If you opt not to spend the night at the Basin Harbor Club, you can continue a short way up the lake on to Otter Creek and proceed up the creek to Vergennes, the smallest city in Vermont.
There are public docks near an interesting waterfall. The town is a walk up the hill and has grocery, shops, restaurants, post office, banks etc close by.
Next Day. Leave Otter Creek and continue North. More choices to make. From here you can stay along the Vermont side or head over to the NY side and see towns along that area. Lots of people go up one side of the lake and then come down the other. Essex is a nice town in NY. Two marinas and a few shops, galleries etc.
Westport, NY is a nice town. Larger than Essex.
Some other places to see are the Shelburne Museum in Shelburne, Vt. It is a car ride (or long bike ride) from the Shelburne Shipyard. That is worth spending the good part of a day.
Burlington, Vt. is a must stop. Lots of culture, shops etc. to see and do there. ECHO (ecology / aquarium / museum) is easy walk from the city marina.
There are a lot of other things to see and do around the mid to northern lake. Plattsburgh, Rouses Point (heck, you can even go up into Quebec for a few days), Valcour Island. Lots of places to anchor out for a night, or a few. Lots of "mom and pop" campgrounds and marinas, bed and breakfasts and resorts. (Check out Hero's Welcome Marina).
Bring your bikes. Hope this helps. Ask more questions!
. We once did Kingston to Whitehall in one day in Mark's old 27 footer. Yes, we left the dock at 4 o'clock in the morning, and yes it was very grueling doing all the locks in one day. But it was doable. So certainly Troy to Whitehall can be done in one day. Of course, you might want to stop along the way and check out the scenery and such, which would make the trip longer...
Plan on 3 weeks!