Originally Posted by imasaluki
Great choice with the O'Day. I'll second the Rhodes 19 for a classy kind of guy.
Cool cool cool boats... and easy on the eyes.
Yes, yes, yes. The Oday Daysailer or the Rhodes 19 would be perfect. Both are easy to trailer, launch and sail, and are very forgiving designs for the new sailor. You can't tip them over or really even scare yourself too badly. And as noted, they are smart looking craft.
Catboats are ok too, but if you have to sail off a lee shore on a regular basis, keep in mind that cats are not closewinded boats. Doesn't sound like a good match to me. But hey, if you are going to use the motor to get someplace else before you sail, that would work.