After purchasing our 1985 Tayana 37 in 2005, we undertook a major refit to prepare the boat for extended cruising. Right after the Annapolis Sailboat Show that year, we loaded up a one-way rental car and drove to Yarmouth, Maine. We were hoping to sail the boat back to our homeport of Annapolis so that we could finish moving aboard, and if all went well, to pack-up our household belongings and put it on the rental market. Then we planned to continue south via the Intracoastal Waterway (ICW) to St. Augustine, Florida, the port we selected for refitting the boat based on the recommendations of several friends in the marine industry in Annapolis.