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.

So you can keep up on things?

I can listen to a little CNN, what’s going on in the news back home. But I can’t do anything about it. That’s the greatest thing: with my job, I have to keep my head so to ground on what’s happening every minute, that I love being someplace where I can’t respond.

Don’t we all?

How many places are there left where you get to do that in the world. 500 miles out, you really are in the middle of nowhere.

What’s the latest with your challenge to Sir Richard Branson?

He said no. Virgin America is launching Chicago that week. They’ve worked for years to get the placements, and he’s there for the launch of every major city. The launch date is in the middle of the race. I’m going to have him on the show and mock him about it, and see if I can get him to change his mind. In the meantime, he says I can borrow the term, Greatest Sailor in the World.

Isn’t that a title he gave to himself?

I’m going to accept it. I don’t care if it’s a false term. I’ll take it. I don’t believe there is a place of Narnia, but I’ll take Aslan’s title if he’s willing to give it to me. 

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.

So it sounds like sailing is getting the patented “Colbert Bump”?

I am bumping sailing. I am America and so this is the real America’s Cup.

Courtesy Comedy Central

"If I can't beat you over the line, then I'll sink you!"

So does that mean Larry Ellison and Oracle Racing are competing for the false America’s Cup?

Ellison’s a fraud, and if he wants to prove me otherwise, he can meet me in Charleston and race me.

Pop Quiz Time: What are the ingredients in a Dark N Stormy?

Ginger beer, and dark rum, and lime.

OK, what specific brand of rum?

Bacardi Dark?

Close, Goslings.

Goslings is one of the sponsors of the race, damn! I got dark rum right, c’mon.

Half credit. Question No. 2. Have you ever experienced the Gold Bond handshake? This is when someone comes up from below, after dusting their privates, shakes your hand, leaving a behind a nice white residue, and you look at your hand and think…

I know the last place that [other person’s hand] was. No, but I have to remember to get some Gold Bond. One thing I did learn was how easy it is to get swamp ass. I had an historic case of swamp ass. You know what’s tough swimming in the middle of the ocean?

Tough as in scary?

When we were becalmed out there for two days, the first day we said, “Hey, let’s go for a swim.” Some people stayed on the boat, so it wouldn’t drift away from us. We put out some lines and some bumpers and we all dove in. Until you look down with goggles on. It was so clear, as clear as air, and I felt immediately like I was falling through the infinitely receding sunbeams below you. And also that something big was about to come up from the depths.

I know exactly what you mean. It almost gives you vertigo.

We were in 15,000 feet of water. It’s absolutely freaky. The odd thing is, it doesn’t get dark, it just gets away from you. It’s like looking at the sky, but down. I’m just afraid it’s going to be filled with a tooth-filled mouth. Every single person who looked down immediately said: “Put out the ladder, I’m coming up.” And we didn’t go swimming again. Plus the next day we woke up, and as far as the eye could see, it was Portuguese man-o-war. 

Do you have any sailing heroes?

Christopher Columbus. Magellan. No, I don’t have any sailing heroes. I wish I did.

What about a favorite sailing song?

Farewell and Adieu You Fair Spanish Ladies, I supposed. Farewell and adieu you ladies of Spain for we’ve received orders to sail back to Boston and won’t be seeing you again. 

Going the more classical route?

I’m going the Orca from Jaws, Captain Quint. Obviously, having grown up in the 1970s in South Carolina, it’s hard to avoid Son of a Son of a Sailor by Jimmy Buffet. It’s extremely difficult. 

That’s not bad, I thought you were working toward Christopher Cross.

No, I’m going to avoid Christopher Cross’s Sailing. Ride Like the Wind or Arthur, but not Sailing. And the Wreck of the Edmund Fitzgerald. And Sloop John B. Actually you know what our sailing song was for two days we were out there and we were just slowly gyring being becalmed. It was Will it Go ’Round in Circles. We were all singing, “Will it go ‘round in circles.” 

There was a [competitor in the race] which was to our port and astern, maybe 8 miles. You could barely see its light at night, and during the day it was just this little bump on the horizon. Of course no one’s supposed to turn the prop because the race hasn’t been called yet. We’d look around and go “Holy s&*t, he’s must be turning his prop. Look he’s going ahead of us.” But the boat’s just turning and we have no reference points, perfectly blue sky, not a cloud. Perfectly flat water, so flat you could see the stars by looking down at night. So we realized that we were slowly turning and the compass was staying still, of course, and so Will it Go Round in Circles by Billy Preston become our theme song for the whole thing.

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.