It may not fit exactly with what you want to do if you want to hug the coast, but Hank Schmitt runs a rally from Newport to the Carribbean, via Bermuda, in the fall. Check out his site, which is Offshore Passage Opportunities: Halesite, New York
. Hank does all the things that rallies do, like provide weather routing, camaraderie, help with all kinds of things, etc. If nothing else, check out his website.