After countless memorable on-field performances in the wet, it seems only fitting that Sydney Swans legend Jude Bolton’s next challenge will be on the water.

Bolton, who hung up his boots at the end of the 2013 season, will set sail with the LOYAL crew in this year’s Sydney to Hobart Yacht Race, which begins in the Sydney Harbour on Boxing Day.

While his football commitments have held him back from participating in previous years, Bolton said sailing in the annual race had always been on his bucket list.

“It’s absolutely something I’ve always wanted to do and it’s something that I was asked to do a couple of years ago by Anthony Bell, who owns the boat,” Bolton told sydneyswans.com.au.

“It’s certainly something that’s really challenging and something I think is going to test me over the time from Boxing Day onwards.

“I think it’s a great outlet to be able to walk straight from footy into a really competitive sport straight away.”

Bolton, who describes his sailing experience as ‘pretty limited’, will work as a member of the sail crew during the event.

“You need upwards of seven or eight people to move these sails because they’re ridiculously heavy,” he said.

“I’m responsible for helping them bring the sail down; so we pick them up, bag them up and put them down deck.”

The former Swan will be in good company in next week’s race and will sail alongside Olympic gold medallist Tom Slingsby, as well as leading Australian sailor Jessica Watson.

Former Wallaby Phil Waugh and television personalities Karl Stefanovic and Larry Emdur will also join Bolton on the LOYAL team, which aims to raise funds for the LOYAL Foundation.

Bolton said he believed the LOYAL crew were in with a chance to contest for line honours.

“Having seen the guys in operation they’re really an elite team, however there are other teams like Wild Oats who have won six times, so it’s going to be a tough task but it’s something that’s going to be a great challenge,” he said.

“Tom is just phenomenal and he’s an Olympic gold medallist and just recently won the America’s Cup and Jessica Watson is such a great sailor that she was able to sail around the world by herself at the age of 16.

“I think we’ve got a really good boat and have got a really good team.

“I’m just rapt to be able to compete in such a prestigious event and to be on a real competitor as well.”