Join Date: Oct 2002
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Lots of good advise here. If you want to read about an amazing couple who bought a cheap, rough 100 year old 28 foot boat in Malta because it was cheaper than renting a flat, look up anything you can about Tim and Pauline Carr. They became enchanted with the boats history, learned to sail her well, ended up becoming sailing legends (they are our heros). I.e. living aboard lead to a whole new life path for them.
Although I don't like to go against the flow, I think I would recommend
learning to sail on a smaller boat, something around 12 or 14 feet. Get out with a local club or take a course. Or even borrow a small boat and get out on the water to learn the magic of sailing. Small boats react faster to sail adjustments, teach you what balance means, teach you to maneuver up to docks under sail and you can't do much damage to anything other than your ego. When you can competently sail the small boat, you will be able to figure out how to upgrade the rig on your 30 footer so it is easy to sail.
Sounds like the beginning of a grand adventure.