We self taught ourselves into flying RC airplanes. Quite challenging, but I think RC sailboats would be fairly easy as long as there is a way to retrieve it if you get boxed in or the wind dies. Looks like there are powered boats available if that happens which might save a long walk.
Remote Control (RC) Sailboats
We found the bigger the plane the easier it was to fly. Don't know if that would be true of boats? Sounds like fun.