1 & 2 Calder's Manual and Cruising Handbook
3 Self Steering
for Small Craft --- John Letcher
4 This Old Boat - 2nd Edition --- Don Casey
5 Dutton's Piloting (and/or Chapman's, but Dutton's better on navigating, Chapman's wastes a lot of space on basics)
Handed Sailing Richard Henderson (there's the online singlehanded sailing book, too)
OK, I cheated, but if I had to choose, these would be the ONLY books I'd need.
I keep referring them to others who ask.
You could also do a SEARCH on this or any other boating
forum and pretty much get the same answers.
All the fiction by Tristan is great reading. Rousmaniere's stuff is great, too.
Anyone who wants to sail SF Bay
: Kimball Livingston's Sailing The Bay, either edition. There are two.
Agree on Sailing for Dummies, too.
Heck, ya shoulda asked for the Top Ten