Join Date: Feb 2007
Location: New Jersey
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Re: sailing r/t Annapolis-New Rochelle, Ny
That time of year, most boats that do so are moving south. I think there's probably a good chance that you could hitch a ride from the NYC area headed toward Annapolis.
Around 9/23. Many southbound sailors time their trip to coincide with the Annapolis boat show, which begins on Oct. 4th this year.
City Island would be a likely place for you to be able to hop on a southbound vessel. Many boats moving south also end up waiting for a weather window to transit the NJ coast in The Atlantic Highlands ( NJ) . There's a fast ferry from lower manhattan that will take you there.
Odds are that there will be fewer boats moving north. I would guess that if you modify your plan to look for a one way trip south you'd be more successful. Or, at least two separate trips. You might get lucky.
It's probably too early to get any commitments, I'd check back in early sept, when people are beginning to move their boats.
It's unlikely that any one boat would be doing a R/T that time of year.