RE: Sailboat; 6'+ Hull Length?
Any of the classes I mentioned would do it for you. For a radio yacht, vintage designs have a weakness - they were designed to run straight, the rudder was really a trimming device. A radio yacht is intended to steer, so changes have to be made. On your link, look at the difference between the IODs and the vintage "A" boat near the bottom of the page.
The difference between a boat and big plane is that you probably wheel the plane to where you want it, then set it off. With a boat, you have to lift it in and out of the water, preferably without joining it. The heavier the boat, the more counterbalancing involved. The bigger the sails, the more interesting the proposition.
The awning and beer seem an excellent idea. Trouble is, sailboats demand attention when on the water. They dont stop, and, like any object of beauty, if they sense that attention s lacking, will wander off. The other odd thing is, if they lack a driver slowing them down, they invariably go faster than you ever thought possible.