If your interested in "the great loop" read the classic "A Year in a Yawl". This is the true story of the first time anyone did it - late 1890's. Whats facinating is it was four young boys who built a Yawl by themselves - and take off - Tom Sawyer-esk. The first edition is 1904 I believe, but re-prints can be found cheap.
Of course the best, IMO, written "Catboat Cruising" story is Plummers, "The Boy, Me, and the Cat". The CBA just put it back in print a few years back....