He started sailing in cat rigged dinghies, International 14s, then worked up to Dragons, a CAL and a custom Kirby 36. When he got on in years he bought a Nonsuch 30. The other keel boats were all called Robin Hood but the Nonsuch was called Square One because he figured it was just like the boats he started out in. His last boat was a trawler but he was a true sailor until the day he died.
They do sail pretty well to windward. Livius even raced his for several years. As long as there was a lot of wind he did ok but jibing in winds over 20 knots can get a little hairy.