Start with high-confidence sailing books, then narrow by subgenre or adjacent topics.
A Voyage for Madmen
Peter Nichols
Sailing Alone Around the World
Joshua Slocum
The Arts of the Sailor
Hervey Garrett Smith
Stress-free Sailing
Duncan Wells
Rigging Handbook
Herb Benavent
The Little Book of Incredibly Useful Knots
Geoffrey Budworth, Jason Dalton
Fifty Places to Sail Before You Die
Chris Santella
