Re: Sailing alone??
You def. want somwthing big enough the she can stretch out and realx with out getting in the way of your need to handle the boat. A 30 foot or so cat is perfect for this. I ran a 30 foot cat single handle as a 6 pack back country charter with no problem. The deck is big and stable and safe. I could get all over the place with 6 lounging guest's and never say" excuse me" You want something she can invite friends on and the fact that they don't heel much and can get into shallow water, run up on a beach even, a huge plus. I had a self tending club footed jib on a windsurf boom and the main was light enough I could raise with out the winch. Hand raise the anchor as well. That boat is called the Java Cat. You can prob see it online at Key West eco-tours. I wish I owned it.
" Some are boat wise and some are other wise"