Thanks for the great advice and encouragement. Yes, I do have an EPIRB on board and have a 4 man coastal liferaft. I was considering getting a Garmin 76 GPS without the charts as I've heard they are a great little unit.
I do have dead reconing skills and know how to use my hand held compass to triangulate my position. I have all the paper charts from Maine to the Chesapeake. I have sailed my Westsail on the bay in 35 knot winds and have done so solo and practiced hoving to. I have a double reef main, a double reef staysail, a 110 jib on Harken roller, a Yankee, trysail, and code O.
I am pretty stuck on my departure time. I would have liked to leave in August but my wife and I run a seasonal business which continues after Labor Day but does quiet down enough for her to handle it alone.
Saying that, I will look for the first good weather window right after Labor Day. I don't have a schedule or time constraints. My intention is to look for a 48 hour weather window leaving Maine and ride a high pressure system from the north.
Good advice also on the route. A three day passage outside may be prudent to the Chesapeake Bay bridge. If weather cooperates, that would be a good alternative. Part of my desire to go inside LI sound is just the adventure of it and sight see.
I have heard from a couple of my Westsail brotheren who are willing to jump on board. Both are X Navy with years at sea and sailing experience. Both are open to as much time needed to make the voyage and can be ready within a couple days notice.
Having some apprehension is not all that bad. I have a LOT of respect for the sea. I agree that it would have been beneficial to have crewed for others to gain ocean experience but I believe I have the skills to get this trip done.
Again, thanks for your sincere comments and suggestions. I hope to see you out on the water.
PS. After getting the boat down to the Chesapeake, I will drive back to Maine, finish the business commitments, and head back down with my wife to the boat and continue to venture south for a few months.