[killarney_sailor]

I agree with Jack about the female only lessons. You want her to be able to sail the boat by herself evn if she never has to do it.

The kind of boat (and the conditions of course) determine much of what is possible. You must have a good autopilot and sail handling systems. For our 36000 lb boat (and I suggest you use displacement rather than LOA for the discussion), we have very reliable inmast furling (and yes I know people don't like it), large jib winches (65s), and an inner stay for small staysail. Actually removing and replacing sails on a big boat becomes almost impossible if you are by yourself - the damn things just weigh so much.

Also, sailing way offshore away from shipping lanes is much easier than where there is traffic, land, and anything else you can bump into.