Proceedings of the Twenty Third Chesapeake Sailing Yacht Symposium held at the United States Naval Academy on March 15 - 16 2019. The proceedings include a collection of 15 technical papers relating to the art and science of sailing vessel design and operation. A detailed bibliography of all papers presented at each of the previous 22 symposia is included. The conference was sponsored by the Society of Naval Architects and Marine Engineers and the Sailing Yacht Research Foundation.