During the summer of 1968, to celebrate his twenty-first year with the Institute, the Executive Secretary sailed his boat Jester in the third single-handed transatlantic race, from Plymouth to Newport, Rhode Island. Of the 35 starters Jester was the last of the boats which completed the course. He here describes the reasons which led him to take a route which extends the distance of the course from 3000 to 5000 miles, and gives an account of the passage and of some of the problems of single-handed sailing.