 Awarded for the best cruise in a yacht up to 30ft overall | ||
| 2008 Sean McCormack Marie Claire II | 2009 Bill Rea Elysium | 2010 Sean McCormack Marie Claire II |
| 2011 Sean McCormack Marie Claire II | 2012 Mike Delap North Star | 2013 Mike Delap North Star |
| 2014 Peter Fernie Mystic | 2015 Conor O’Byrne Calico Jack | 2016 Conor O’Byrne Calico Jack |
| 2017 Duncan Sclare Freebird | 2018 Peter Fernie Mystic | 2019 Conor O’Byrne Calico Jack |
| 2020 Conor O’Byrne Calico Jack | 2021 Conor O’Byrne Calico Jack | 2022 Conor O’Byrne Calico Jack |
| 2023 Paddy Barry Drascombe Lugger | 2024 Conor O’Byrne Calico Jack | |