Stephen Colbert Featured in Sailing World Magazine.

Stephen Colbert Challenges You to an Ocean Race.

Stephen Colbert’s first offshore racing experience, the 2005 Charleston to Bermuda Race, couldn’t have gone any worse. The 45-foot cat ketch on which he sailed finished dead last. In fact, it took his crew so long to reach Bermuda, they arrived two days after the awards ceremony. But as unequivocally bad as it was from a racing perspective, as an experience, it was equally as profound. In fact, the normally glib 46-year-old, who hosts the satirical news show “The Colbert Report” on Comedy Central, says he has trouble finding the words to accurately explain why he enjoyed the 777-mile race so much, and why, come May 21, he’ll do it again.

What’s your sailing background?

I grew up right on Charleston Harbor, right across from the Carolina YC. The regattas were right outside my window. I wasn’t allowed to go sailing because I don’t have an eardrum in one ear and I couldn’t get water in my ear. It just drove me crazy. My mom felt so badly for me, that when I was 20, my doctor said, it’s healed enough—the thing that was wrong was still wrong, but it was better—he said, “You can go out there now.” My mom said, “OK, I’ll get you sailing lessons.” I said, “I don’t really want to now.” Which, of course, really upset her, because to her I was still a little boy. But, I said, to hell with it. I’d moved on.

So I kind of just left it behind. I’d done a little sailing, I’d snuck behind her back, and capsized, and got in trouble. But I hadn’t really done that much sailing, but the little I’d done I had enjoyed.

Then [in 2005] when I was 41, a friend called up and said, “The C2B [Charleston to Bermuda] is this year. I know somebody who’s got a boat, and you know almost all the guys on it. Do you want one of the berths on the boat? I asked my wife, and she said, “Yes. Go.” She shocked me. That was my introduction to serious sailing. I just loved it.

This past summer when we were down in Charleston—I hadn’t decided to do the C2B this year, the Charleston to Bermuda that OnDeck is doing. One day I was looking out, it was a beautiful day; I was down there for a couple of weeks. I actually called up OnDeck, not knowing I was calling up OnDeck, because they took over the maritime center in Charleston, and rented a Beneteau to take it out. Then I found out they were running the race and that’s how the whole thing started with me back involved with them again.

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So this time around, what non-essentials are you going to try to sneak onboard for the trip?

It was a dry cruise last time. The captain said, “I want to be clear, this is not a booze cruise. This can be dangerous business and I want everybody sharp. No one’s to bring any alcohol.” After that whale came up and drifted away from the boat, the captain said, “OK, wherever you’re hiding it, you can bring it out.” And every single person had brought liquor on the boat. Then we all had a cocktail. So I suppose I’ll bring a bottle of gold rum. You know what I’ll bring, an XM radio. It’s not supposed to work that far out, but it does, it works all the way to Bermuda. That’s what I learned last time.

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What sort of coverage of the race, before during or after, are you planning for your show?

There’s a cult that says the world is going to end on May 21, 2011. That’s why the race starts on May 21, because I’m leaving the country before the rapture. If I get raptured, it’s better to be at sea because I’m not going to bump my head on anything as I get raptured up. And if I’m not raptured, if I’m left for the tribulation, I want to be in international waters, so God can’t extradite me, because I don’t think he has an extradition treaty with Neptune. That’s one of the ways I will talk about it on the show.

I also will encourage other people to challenge me because I have declared myself to be the Greatest Sailor in the World. Since Sir Richard Branson forfeited, I’m the Greatest Sailor in the World. One thing that’s sincerely made me happy is with the economy the way it is, the last two sailings of the C2B have been very sparse, but I think they already have more boats committed at this point than they had even the year I did it. It’s my hometown, I’d like this race to be bigger.

I challenge anyone if they think they can beat me. I’ll see you on the dock and I’ll see you in Bermuda and I’ll throw the party if you win.

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Last question. Is there anything that you’re especially looking forward to with this race?

Spending more than 12 hours in Bermuda would be nice. [In 2005] we arrived at 10:30 p.m. on Saturday night and I had a 10 a.m. flight the next morning. So I literally came in, took a shower, tried to sleep—which was impossible because the room wouldn’t stop spinning—and then I had to get on an airplane the next morning.

Well booking a 65-footer is a good first step.

That was part of the impetus. I’d like to maybe play a round of golf and have a Dark N Stormy.

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Full Interview: Sailing World.com