Join Date: Aug 2007
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If you are trailering in Minnesota, I'd avoid the fixed keel Capri. Shallow launch ramps and shallow lakes make a centerboard more practical.
Others have suggested 22 footers... yes they are "trailerable" but you'll quickly tire of rigging and launching for anything less than an overnight... too much work for a daysail. I've raised the mast on an O'Day 222 with one other guy and I'd only do that for a season, maybe a weekend but NEVER for a daysail.
Carefully consider your overnighting prospects. If daysailing is really the desire, then you can go to things like O'Day Daysailer (my mid-fifties wife and I can launch and retrieve in ten minutes), Flying Scot, Rhodes 19, etc. Cheap to buy, easy to trailer, fun to sail, spacious cockpit... just no cabin.