Wolf and PCP thanks for the great advise. I was looking at something called "Sailtime". I can do bareboat charters on their boats and get to know the ropes as it were. I have been looking for awhile and I have narrowed my choice of manufacturer's to Ericson, Hunter or Catalina. I checked out some Island Packets also but just too pricey for my first boat. I will be looking for a boat between 34 and 38 feet for myself. I will be cruising the Chesapeake Bay for the first couple of years to get to know her and then after that, go out on some longer range voyages. Again thanks for the good advise!
If you have never sailed before, at all, you would be better served to learn on something of the 15 foot range. A bigger boat is more stable and less sensitive. If you can handle a smaller boat, a bigger boat is easier. The boat I taught myself on was a tender 10' moth-like dinghy. Later, when I got my holiday 20, it seemed as stable and steady as a rock.
But, if you learn sailing on a cruising yacht, the day you have to sail a smaller boat, like a dingy, will be a shock.