Shane Acton was in his mid 20s and mostly broke when he decided he would like to go sailing. He had absolutely no sailing experience but was brim full of confidence and, as events would prove, with competence. He spent months searching for the right boat and finally found Shrimpy a 5.5 meter twin-keeled yacht with a draught of just 1.5 feet. The yacht was a Caprice, made of 3/8" plywood, with an enclosed cabin and 2 bunks.
While he was searching for the boat he taught himself celestial navigation, and made a bit of money along the way teaching it to other yachties. So, armed with a few charts, a plastic sextant, and enough food and water for a few weeks, he set out from Cambridge and began his 8 year voyage around the world.
Along the way he made many friends, found employment when he needed it, and met a beautiful young adventuress from Switzerland who joined him for most of the voyage. He makes light of most of the hazards and difficulties, and concentrates on the beautiful far-off locations where they spent most of the journey. In fact, the only really serious difficulty that he got into was in the Red Sea when the boat was lifted 3 meters in the air and dropped with a thud, cracking the plywood bottom. He was able to effect a temporary repair with greasy rags, which actually lasted until he arrived weeks later in Cyprus.
This book definitely makes my list of favorite sailing stories. Some others that I like are Alone Against the Atlantic by Gerald Spiess, Sailing Alone Around the World by Joshua Slocum, and Two Years Before the Mast by Richard Henry Dana.
Sadly, I think that Shrimpy is now out of print, but it is available used from Amazon.