My husband asked me that same question ( I had only been on a sailboat 3x sailing trips to our local island before -but on dive boats lots) 3 yrs ago. We looked until we found one we thought we could live on easily & sail well enough too. I was still working so he went in search. He found the boat & I moved on sight unseen. (I saw only photos by email) We left 2 months later for Ensenada, Mexico
and for La Paz
3 months after. 3 years later we still love it. I am back working- getting ready isn't tough once you have a routine. The life is great. You have to be adaptable, adventurous & ready to stick it out together no matter what. A cute book for your gf to read is The Motion of the Ocean: 1 small boat, 2 average lovers & a Woman's Search for the Meaning of Wife by Janna Cawrse Esarey. It's a humorous look at a couples time sailing & their relationship.