As said before, you have the 3 legitimate options.
1.) East through Trent Severn waterway to Lake Ontario to Oswego Canal to Erie Canal and then Hudson. This is good if your near the Georgian Bay. This option has VERY little actual sailing.
2.) Lake Erie to Erie Canal to Hudson. This is easy, quick, low cost (one cheap canal), and you can sail on Lake Erie and Huron.
3.) Lake Erie to Welland Canal to Lake Ontario to Oswego Canal to Erie Canal and finally the Hudson River. This option allows you to sail the great lakes, but may be a day or two slower than the Erie Canal route (unless you sail all night). Note: Need three people on the Welland Canal.
Of the three, Lake Erie to the Erie Canal would be my choice.
The complete Erie Canal route from Lake Erie to NYC will take about 10-13 days depending on how much you motor per day. The mast must come down before entering the canal, and can be put back up just south of Albany. There are 35ish locks, but after you do one, you've done them all. You should get the 10 day pass, which will be available at the second lock in Lockport (the first lock is free).
Once on the canal, most towns have terminal walls you can stay at for free. Some also have power, water, restrooms, etc. too (rates vary from free to $1/foot).
Once on the Hudson, its pretty narrow and thus difficult to sail till you get close to NYC. Also planning to go out with the tide can make all the difference in the world.
Let me know if you have any specific questions.
Boat: O'Day 25 / Sea Ray 270 Flybridge
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