The Newport Bermuda Race began in 1906 and occurs every two years in June. Sailors from around the world sail from Castle Hill Lighthouse in Newport, RI to St. David’s Lighthouse in Bermuda. The race takes anywhere from 2-6 days to complete and is considered very difficult but addictive by sailors. The race actually began as an act of rebellion by Thomas Fleming Day when the ‘Establishment believed that it would be insane for amateur sailors to race offshore in boats under 80 feet.’ It’s rumored that three boats under 40ft were each given funeral wreaths. The winner of this first race was Thomas Fleming Day in a 38ft yawl Tamerlane.