The Plan, just having bought a 1983 Bruce Roberts Spray 36A steel cutter, is to renew the hull then cruise clockwise from NW Florida or Alabama through the Caribbean this year (Fall, Winter 2013-14 Spring). Then sail up the western Atlantic and cross over to northern Europe for summer 2014. I am not sure how I am going to keep my house...
and do all of this preparatory sailing. Once I get through the Panama Canal I do not foresee returning to the Americas for a year or two. Maybe I will have to sell the house.
Anyway, a good year or two of sea trials ought to be enough time to see how I do and the boat does in challenging conditions. I imagine replacing standing rigging, running rigging and adding a set of sails. The galley and head may need some refitting.
Any leads on water catchment? The boat is in Florida now. Add udders to the awning and mains'l cover?