"Tinkerbelle" by Robert Manry. True tale of a newspaperman with limited sailing experience crossing the Atlantic in a 13 foot sailboat. As opposed to many books of this type Manry has some truly insightful things to say and an eye for the telling particular. He left the U.S. on the sly as he didn't want his friends to think he was crazy, only 3 or 4 people knew he was going in a 13 foot boat. He was at sea and out of radio contact for 78 days; in that time the story travelled around the world, he was expecting a quiet arrival in England and was shocked when the Royal Navy and 50,000 people were waiting to greet him.
"Longitude" by Dava Sobel. Another true tale, this one about John Harrison who spent 42 years solving the puzzle of determining longitude. If you like "Bowditch" and other navigation geek books you'll love this one.
"Modern Seamanship" by Don Dodds, specifically the chapter on anchoring. If you're a geek or engineer this is the most fascinatingly technical explanation of proper anchoring technique I've ever read. Also "Modern Cruising Under Sail" by the same author.