Also try a Flying Scot. I owned one for 15 years and it is a great boat to learn to sail. It also is very stable and has built in flotation. The large cockpit will allow you to get four on board comfortably. Its a 19 footer and easy to haul on a trailer. My trailer had a release in the center and the boat easily slipped into the water; same on loading. Its a fractional rigged sloop with a spinnaker. You should be able to get a used one for anywhere from $3,000 to $7,000 with the trailer. Good luck.