Rolex Sailor of the Year Award

Sail Canada Rolex Sailor of the Year winners are individuals who have provided global recognition to Canadian sailing and Sail Canada. They are renowned leaders who have attained high levels of excellence with results and accomplishments around world events or activities. Along with recognition for exemplary sportsmanship, they have held the respect of their fellow sailors.

Sail Canada recently accepted nominations for the Rolex Sailor of the Year Award based on the time period from December 2nd 2019 through to August 6th 2021. Nominees are individuals who:

  1. Have been significantly involved in an activity that, through the year, has provided recognition to Canadian sailing and Sail Canada. Results and accomplishments in world settings are considered in recipient selection, with priorities given to leaders who have attained high levels of excellence in Olympic/Paralympic class sailboat competition.
  2. Have shown leadership qualities with respect to an event or activity.
  3. Demonstrate sportsmanship and the gaining of respect from fellow sailors.
  4. Are Canadian citizens or permanent residents of Canada.



Sail Canada’s Rolex Sailor of the Year will be awarded at Canada’s Celebration of Sailing reception. Join us! Find details around the next Celebration of Sailing event here: Canada’s Celebration of Sailing



The award was first presented in 1986 to America’s Cup supporter Paul Phelan, who successfully organized a merger between Canada’s top 12-meter syndicates. To date, the Rolex Sailor of the Year has been awarded to many more outstanding Canadian sailors.

Previous Winners

2020-2021 – Sarah Douglas
2019 – Sarah Douglas
2018 – Tom Ramshaw
2017 – Brenda Bowskill
2016 – John McRoberts & Jackie Gay
2015 – Lee Parkhill
2014 – Eric Holden
2013 – Terry McLaughlin
2012 – Oskar Johansson
2011 – Paul D Phelan
2010 – Fredrik D Eaton
2009 – Curtis Florence
2008 – Paul Tingley
2007 – Evert Bastet
2006 – Michael Leigh
2005 – Chris Cook
2004 – Ross MacDonald and Mike Wolfs
2003 – Derek Hatfield
2002 – Stephen Tupper
2001 – Terry McLaughlin
2000 – Livius Sherwood
1999 – Richard Clarke
1998 – Dirk Kneulman
1997 – Gerry Roufs
1996 – Bill Abbott, Joanne Abbott and Brad Boston
1995 – Ross Cameron
1994 – Paul Henderson
1993 – Karen Johnson, Jennifer Normand, Suzanne Calladine and Cathy McPherson
1992 – Ross Macdonald and Eric Jespersen
1991 – Hank Lammens
1990 – Ross Macdonald
1989 – Andre Julien
1988 – Lawrence Lemieux
1987 – John Hughes
1986 – Paul J. Phelan, CM


  • Rolex
  • Helly Hansen
  • Gallagher Skippers' Plan
  • BMO Sail Canada MasterCard
  • Government of Canada