Re: ? Sail from Lake Erie to Florida late August
Have at it!!! There will be a reasonable amount of staging to pull the mast, transit the canal, then restep and tune the rig. Perhaps even have the stick shipped to the other end. Several of us have done it, if you need tips.
Then you head down the Hudson, which I had no appreciation for when I was young and growing up just north of NYC. Now, I find it one of the most beautiful rivers in the world.
Its not until you decide to exit the Hudson that you really need to worry about hurricanes. You should have plenty of notice to plan for a contingency along the way. You should check with your insurance company, however. They typically won't cover you below the Carolinas until after Nov 1, unless you have that included and pay more.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.