O'Leary will be part of a 10-boat Irish contingent heading to Scotland, but the Irish are by no means the farthest travelled as France's Gery Trentesaux from Brittany is also racing.
O'Leary, who has charted the Ker design from Colm Barrington for this years Commodore's cup, learned that the assymetric arrangement was adequate for reaching but poor dead downwind.
O'Leary has borrowed a pole, and new spinnakers are being made this week for the biggest event on the Scottish calendar, an event the Royal Cork sailor has twice won.
The introduction of the new 'Scottish Round the Island' Race is an addition to the event for the CYCA fleet this year.
Those who do travel can expect to race against an impressive and highly competitive field. Participants include last year's overall winners Mark Mansfield, Conor Phelan and the crew of Conor's self built vessel Jump Juice, who will be competing for the top spot against Anthony O'Leary, title winner in 2006.
Twice winning captain of France's successful Rolex Commodore's Cup Teams, Gery Trentesaux, returns to Tarbert, Loch Fyne over the Whitsunday Bank Holiday weekend in search of his first ever overall Class win at the Bell Lawrie Scottish Series.
It will be Trentesaux's sixth time racing on the esteemed Scottish waters. In 2002 he was second overall with his IMX 40 Courrier Nord, just pipped by Ireland's former Commdore's Cup team captain Colm Barrington on his Gloves Off.
Lille-based entrepreneur Trentesaux, who has kept his string of 'Courrier' named yachts in picturesque Brittany for many years, admits that his love of the picture postcard Scottish surroundings is an even bigger draw than the chance to test the form of several of Ireland's top yachts, who will likely prove formidable opponents again when the Rolex Commodore's Cup takes place on England's Solent in June.
The Rolex Commodore's Cup is the most sought-after international three boat team event raced under the worldwide IRC handicapping system.
Other entrants include Ewan MacKay and the crew of Haggis who came second in the sports boat class last year and hope to steal first place this time round. Northumbrian, Nik Aitkinson, who made an appearance on local news after crashing into the Millenium Bridge on the river Tyne, will be taking to the water on his boat CORKANUT to compete for his fifteenth year at the Scottish Series.
A new competitor to the event, Phil Eagleton will be racing his boat Chia Chia, which has previously been sailed to victory under another helmsman winning the overall Scottish Series title in 1986. Also Fiona Hicks, who was part of the very first all female crew to compete in the Round Ireland Race, will also be competing with the crew of No Angel.