The Irish Sailor of the Year Awards began in 1996.

The awards are administered by Afloat, Ireland's boating magazine.

• 1996 Mark Lyttle
• 1997 Tom Roche
• 1998 Tom Fitzpatrick & David McHugh
• 1999 Mark Mansfield
• 2000 David Burrows
• 2001 Maria Coleman
• 2002 Eric Lisson
• 2003 Noel Butler & Stephen Campion
• 2004 Eamonn Crosbie
• 2005 Paddy Barry & Jarlath Cunnane
• 2006 Justin Slattery
• 2007 Ger O'Rourke
• 2008 Damian Foxall
• 2009 Mark Mills
• 2010 Anthony O'Leary
• 2011 George Kenefick
• 2012 Annalise Murphy
• 2013 David Kenefick
• 2014 Anthony O'Leary
• 2015 Liam Shanahan
• 2016 Annalise Murphy
• 2017 Conor Fogerty
• 2018 Robert Dickson & Sean Waddilove
• 2019 Paul O'Higgins

Yes. The boating public and maritime community can have their say to help guide judges in deciding who should be crowned Ireland's Sailor of the Year by using an Afloat online poll). The judges welcome the traditional huge level of public interest in helping them make their decision but firmly retain their right to make the ultimate decision for the final choice while taking voting trends into account. By voting for your favourite nominee, you are creating additional awareness of their nomination and highlighting their success.

Anthony O'Leary of Crosshaven and Annalise Murphy of Dun Laoghaire are the only contenders to be Afloat.ie "Sailors of the Year" twice – himself in 2010 and 2014, and herself in 2012 and 2016.

In its 25 year history, there have been wins for 15, offshore or IRC achievements, nine dinghy and one designs accomplishments and one for adventure sailing.

Annually, generally in January or February of the following year.

In 2003 Her Royal Highness Princess Anne presented the Awards.