I was lucky to grow up in the golden age of small boat racing and family cruising. This book describes my sailing history from our family cruising in a bugeye, sea scouts in Tech dinghies and my first boat, racing a Shearwater catamarans. Like many professionals, I returned to cruising in rebuilding a "homemade "catboat, and cruising in a Hunter 25 and Erickson 35 on the Chesapeake. When my wife and I decided to give up cruising, I returned to racing, built a fiberglass Chesapeake 20 and now own a historic 1939 Chesapeake 20. In moving to Sarasota FL, I found kindred sailing friends and began racing E Scows and MCs on Sarasota Bay. I kept logs of the boats and cruises over 60 years. Each chapter describes the sailboats that my family or I have owned, the cruises, racing and stories, many of them written by my wife, Judy.