Two-time America’s Cup champion Jimmy Spithill is a man of many crafts. Next month he’ll compete in the Devil’s Isle Challenge for the second year, then captain Team Oracle at the America’s Cup. Photo: Sam Greenfield

2x America’s Cup champion Jimmy Spithill talks Bermuda’s 40-mile SUP race

Jimmy Spithill is a man of many crafts. He’s is the skipper for Team Oracle and has won not one, but two consecutive America’s Cups. He’s competed at Molokai 2 Oahu twice and completed the 32-mile crossing both times. He’s flown planes at Red Bull events and with the Blue Angels. These days, you can find the 37-year-old Australian living on Bermuda with his wife and two kids, but with the 35th America’s Cup coming to the island May 26-27, he’ll probably be on the water training with his team. But Spithill’s packed agenda doesn’t stop him from taking on the occasional SUP race, and on May 7 he’ll be competing in the world’s longest open-ocean paddleboard race—the second annual Devil’s Isle Challenge. Chalk it up to a training day. We caught up with the renaissance waterman for a quick chat between sailing sessions and this is what was said. Inspired much? –MM

You're considered to be one of the best, fittest most experienced sailors on earth. How prepared are you for a 40-mile paddleboard race?

It's going to be tough. I haven't paddled much lately because there's just not enough time right now. With the (America's Cup) coming up my days are very long and we're working as much as we can. So it's been tough getting miles on the paddleboard, but I still want to do Devil's Isle Challenge. I love the race and how tough it is; it's a good way to test yourself, especially with the timing of America’s Cup.

When you do find the time, what type of paddling do you usually do around Bermuda?

On our team we have an ex-ironman and a few people who are into ski-paddling, but a few of us are into standup and on the real windy days we will load up our big America's Cup chase boats with boards and go miles upwind, then jump out and paddle back. We have had some awesome downwinders here and there are some really nice stretches of water here when it really gets going.

Some bumper stickers say “My other car is a BMW.” Jimmy Spithill’s says “My other SUP is a sailboat.” He ain’t lieing. Photo courtesy of ORACLE TEAM USA/James Spithill

This will be your second consecutive year competing in Devil's Isle Challenge. Are any other America's Cup contenders racing with you?

Anders (Gustafsson) from Team Artemis—an ex-Olympic kayaker who set the course record for a solo kayak last year—might compete again this year, too. There may be a few guys from other teams going for it as well. It'll be really cool if they do.

How does a SUP race like Devil's Isle Challenge help you prepare for a sailing race like the America's Cup?

Operating our sailboats is very, very physical and standup paddling works a different set of muscle groups, so the physical side of Devil's Isle Challenge is an attraction. But the real attraction is the mental test. 40-miles is a long way to paddle, and it's not like M2O where the wind and waves can help you out. Here the course is surrounded by reef and the wind often works against you. It's a grind, but mentally that challenge is part of the reward if you are able to overcome it.

What’s 32 miles of open ocean paddling for a two-time America’s Cup champion? Another day in the office. Spithill crosses the Ka’iwi Channel at M2O. Photo courtesy of James Spithill, Facebook.

If a 40-mile SUP race is just another prep day for your sailing endeavors, the daily training for Team Oracle must be tremendously intense. How does pausing that rhythm for a day of paddling affect your preparation?

With how long and involved our team's working days are, breaking free to paddle for a day is refreshing because it gives you time to really think. Obviously you'll be thinking about your technique and trying to get everything out of each stroke and bump, but it's also a great opportunity to really think about Team Oracle's campaign. Sometimes it takes that sort of isolation to think things through without distraction.

What's the biggest difference between sail racing and SUP racing?

In sailing we work with a team of more than 85 people to make our craft go. Every day, every outing is a big operation. In contrast, paddling is an individual sport, and especially in the long-distance stuff you're doing it more or less on your own. The simplicity is kind of cool. Just pick up the board and paddle and off you go.

SUP Magazine will be onsite for Devil’s Isle Challenge reporting the event live from Bermuda. Look for more from Jimmy Spithill around the date of the event, May 5-7.

What is the Devil’s Isle Challenge?

Meet some of the other athletes competing in Bermuda.