It may be apostasy to whisper the name on this forum, but I cut my boating teeth on Donald Street's The Ocean Sailing Yacht, Volumes 1 and 2. Yes, I know he spent most of his long life running an engineless wooden yawl around the Caribbean, but man, you can't read a chapter without picking up a bit of "streetwise" advice about keeping your vessel afloat and safe, preventing trouble, or getting out of trouble. Street belongs on any mariner's bookshelf.
Lots of valuable works mentioned above, like Chapman's and Dashew. I'm surprised that no one has so far named Robert Beebe's Voyaging Under Power.
Both to educate yourself as well as to resolve arguments, find a copy of Farwell's Rules of the Nautical Road, Eighth Edition, by Craig Allen (Naval Institute Press, 2005). Farwell's doesn't just spell-out the rules, it explains their genesis and how centuries of accidents and admiralty law have shaped them. Every rule has a history!
