Re: Finger Lakes,NY to Key West,Fl.
As you travel down the Hudson, think about stopping in Cold Spring. I'm not sure about draft at the docks there. Years ago (pre 9/11), I know you used to be able to tie up at West Point. If you still can, its worth seeing. I have a feeling you can't now.
If any in your family are hikers, my favorite trail is about 2 miles outside of the village of Cold Spring. I lived nearby many years ago. It goes up the side of a ridge immediately next to the river and views of the Hudson River and surrounding Highlands are spectacular. Bring lunch and you'll find several places to stop along the way. It is a serious hike however.
Breakneck Ridge Loop | New York-New Jersey Trail Conference
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.