Awarded to the First Overall boat in the Islands Race
| Year | Sailor Name(s) | Boat Name | Boat Type | Results |
|---|---|---|---|---|
| 2024 | ||||
| 2022 | Roy P. Disney | Pyewacket | Volvo 70 | |
| 2021 | Hill Blackett III | 'io | Antrim 27C | |
| 2020 | John Schulze | Horizon | Santa Cruz 50 | |
| 2019 | Thomas Furlong | Vitesse | RP 52 | |
| 2017-2018 | Roy P. Disney | Pyewacket | Andrews 68 | |
| 2015-2016 | Chris Hemans | Varuna | Rogers 46 | |
| 2014 | Brack Duker | Holua | Santa Cruz 70 | |
| 2013 | Peter Tong & John Sangmeister | OEX | Santa Cruz 70 | |
| 2012 | Tom & Terri Manok | Pole Dancer | J/120 | |
| 2011 | Andy Rasdal | Valkyrie | TP 52 | |
| 2010 | Paul Casanova | Flaca | Santa Cruz 50 |