Star sailor Rudy Bailey will be gunning for a hat-trick of Flag Pole to Flag Pole titles when the Comet Fleet sets sail from Hamilton Harbour to St. George's Harbour on Sunday.

The West End Sail Boat Club stalwart has dominated this race for the past two years and if all goes according to plan this year he hopes to make it three on the trot.

Bailey has made a positive start to the 2009 campaign having dominated inter-club racing in the Great Sound last weekend to capture the Lee Hayward crown.

He also finished runner-up in the Burchall Brother's Bowl earlier this month.

The Somerset resident and well-known taxi driver will not reveal the identity of his crew until the actual day of the race.

"I have two crews. I have a plan A and B and so who is going to be in the boat is all up to mother nature," Bailey said.

Bailey is confident he can rise to meet the challenge but admits he has his work cut against arch-rival Stevie Dickinson and club-mate Gladwin Lambert who won this year's Burchall Brother's Bowl with crew Greg Proctor.

"I am a bit concerned about Gladwin because he is going extremely fast this season," he added.

"With all his experience and help from me he has gotten extra fast. It could be a three-boat battle between Dickinson, Gladwin and myself, or if Stevie and I get tangled up Gladwin could just sail away from both of us. Stevie is my equal or better on any given day.

"But I'm ready to sail. I have won several races already and if I can keep the boat upright I think I can sail fast."

Dickinson finished second last year followed by Lambert in third.

Last year's race ended in controversy when Dickinson claimed Bailey sailed in a lighter boat to gain an unfair advantage.

And in what is believed to have been an unprecedented move, the entire Comet fleet was weighed with Bailey's boat proving to be within regulations.

Bailey's demands for an apology from Dickinson fell on deaf ears.

Meanwhile, Royal Bermuda Yacht Club's Contest III will defend its Heritage Cup, Anniversary Cup and Leon D. Fox Cup titles when the 2009 Fitted Dinghy season gets underway on Sunday in St. George's Harbour.

With skipper Somers Kempe at the helm, Contest III made a clean sweep of top honours, including an unprecedented six straight Heritage Cup crown, in the East End in last year's event.

Kempe and crew also successfully defended the Leon D. Fox Cup.