A trailerable that I''ll always regret parting with was a Holder 20. It''s an older boat, large cockpit but with a small cabin that you could sleep in if you were so inclined, but its tight. It has a drop keel with a bulb on it and a pin to keep it in place so it is like sailing a keel boat after launching it, but it is easy to trailer and launch on a ramp. Great sailing characteristics with some zip. I really miss that boat.
check out the Tanzer 14 or 16 for easy trailering, rigging and great sailing/ another great boat is the Mercury 15, centre board by Cape Cod Ship located in Wareham, Ma.