JohnB, Redherring had some good advice for a newbie... why not hire a skippered charter
on a vessel about the size and accommodation you are looking for in the area you intend to cruise
? Not only will you get some hands on experience without the large capital outlay, you will get to know the boat over a week or so and see if the area appeals to you for a longer term stay.
There are many folks who thought this lifestyle was for them on the boat of their dreams only to find it didn't meet their initial expectations. Good luck with your search. Phil