Annapolis is perhaps the most active competitive sailing community in America. I am willing to wager that every Jr college or community recreation association in the area has a sailing program.... Take advantage of your resources...... sure you can read "sailing for dummies" and throw your boat in the water and blindly venture out with one hand on the tiller and the book in the other...... but ....why?
If I were you, my first google search would be "sailing programs in the Annapolis area" .... sign up for one of the classes... learn to sail a dinghy and you'll meet some cool people....
Second search would be for the local Catalina 22 fleet... you need someone to show you how to set up the boat.... that connection will perhaps lead to a sailing buddy..
