This is my first post here. I too singlehand. I purchased a Westerly last year, lived aboard it in Md., and when spring arrived I sailed it alone down the Chesapeake to Va. My first thought was to have it delivered to Va., but I knew I just had to sail it myself. Yes, my little ship and I bonded.
The sail down was the greatest experience out their alone. While sailing to VA., I anchored out once and docked at two marinas along the way. Stopped at a little village - Reedville - strolled the main street - found a nice little ice cream shop, and just enjoyed the quiet little creek. Next morning the fishing boats were out early, as I was, and I had a wonderful sail down the Bay. Fellow sailors were extremely nice and helpful, and yes I did get some "I can't believe you're doing this by yourself" when it was realized a woman was sailing alone; and I am not a spring chicken - 58 yrs. young.
My Westerly is presently on the hard, bottom painting, etc., as I am trying to learn everything I can about maintenance, with the help of my brother.
I plan on taking the ICW route in another year. I can't imagine doing anything else, but being out there.