2026 Everglades Challenge: to the End

To get a sense of my favorite skipper's 2026 Everglades Challenge,  you could just watch this video clip from Nate "Natedog" Villardebo on repeat for 94 hours, 8 minutes, and 22 seconds. 

And a glorious sunshiney adventure it would be.

You could alternate with the following video from Jahn Moresailesaid's pre-race delivery to Fort DeSoto for a little variety on the 327.07 miles.

​But as any sailor will tell you, it's never just chamber-of-commerce weather and champagne sailing.

There was equipment failure, storms, doldrums, and of the 94 hours (Saturday morning till Wednesday morning) only about 15 hours of sleep.

Plus we severely under-packed electrons.  

​The water ballast tanks, which help keep Zygote hiked flat against the wind and allow the carbon-fiber creature to move like a scalded cat are powered by a nifty Lithium battery that fainted on day 3. Which meant that my favorite skipper, TwoBeers, was obliged to sail at turtle pace.

Likewise, the repowering packs for his phone, GPS, etc. gave him their best efforts and then said, "Go on without me, Comrade."

Still, TwoBeers had only just finished building Zygote, and his stated ambition was to simply get the boat from St. Pete Beach to Key Largo. 

At the risk of encyclopediaing this trip, TwoBeers' adventure went a bit like this:

Spotting Andyman and Natedog coming in Rabbit Pass, TwoBeers paused on his way out of Check Point 2 by Chocko Island so he could buddy-sail with them.  

Was he short of navigation? I ask. Nope, the tablet AND the Garmin were operational.
He just wanted to hang out? Yeah.

​Plus Andyman lent him his extra paddle, since of course the pedal drive had busted 13 hours into the adventure.

As it turned out, that nice long kayak paddle, a back-up to the pedal-drive, was still in the van. Oops. ​

Andyman and Natedog highlighted in red because their tracker lost track for a bit...

The two boats, plus Crazyrussian on a catamaran, leapfrogged their way together all the way to Check Point 3.
​On the RaceOwl site, the three boat names often covered one another, nestled like spoons on the virtual map.

Watching from shore, I saw  a distinct cowlick as the wind shifted and swirled just shy of the Cape Sables, and I imagined it was going to be an unpleasant sail through it. Gusty conditions (to 59 mph!) possible.

I texted my intel. It's one of the nice things about this race, you can call or text or send smoke signals during the event. 

I was, sadly, right about the cowlick.  "Every time the place I wanted to go was 45 degrees off the bow, the wind came around on the nose. And piped up."

"I went right up to shore at the capes," Jeff said. "The waves were so much less awful in there, but I had to short tack over and over. I can't wait to see my track. It must be 90 tacks I made."

"Yeah," Andyman said. "It was so gorgeous for a while, and then it wasn't."

Zygote made it to the entrance to Flamingo, Check Point 3, first of the three, but did not enter the tiny pass. His tracking dot paused. I figured he was waiting for a favorable tide. 

So when I woke up at 5 to see he'd moved, but not very far, I was a little concerned. Maybe his anchor dragged, I thought.  Then at 6 his dot was crawling again, only it seemed erratic. Hmmmm.  

At 630, I was actively worried. Twobeers appeared to be sailing AWAY from the checkpoint. Lack of sleep can do terrible things to a person. Not just to the racer, but to the ground control as well, to be honest.

At quarter to 7, I did the thing: I called the Checkpoint captain at Flamingo.  Hi, I said, hey, I'm a little concerned about TwoBeers. Could they see him? I was worried that my skipper might be losing his ever loving mind. I think I actually used that phrase, a nod maybe to Bones on classic Star Trek. 

Gil at Flamingo assured me that I was doing the right thing by calling. It was, he told me gently, too dark for him to see anything (damn Daylight Savings Time), but that he'd take a look as soon as he could. As we talked, Jeff's tiny blip on the map turned around and started creeping toward to Flamingo.  ​

45 minutes later, an unknown number called: Gil made Jeff talk to me to assure me that he was compos mentis. My skipper sounded cheerful and still determined to get to the finish. Tom Ray, bless his photographer's eye, posted a lovely proof-of-life photo on Facebook. 

To the Finish Tuesday to Wednesday morning
From Flamingo, the wind was out of the northeast at around 7, making it a beamy reach, and while both Andyman and Jeff tried for the eastern route, there just wasn't enough water. Being short on navigation power, Twobeers decided to shadow Andyman. They faffed around for a bit and then pointed their boats along the conservative southern route across Florida Bay. 

Sailorking and Possum at the finish!

SailorKing and Possum, leaving Flamingo at the same time, did not faff around, having already decided on the southern route. As Jeff said, "They slaughtered us."

Without water in the ballast tanks, Zygote struggled to stay upright once the breeze gets up over 10. This is a fact that the boat had made abundantly clear to Jeff, but was much less obvious to his buddies Andyman and Natedog aboard their Highlander, Bubbles Up.  

Why was Jeff going so slow? What was wrong with him?   A flurry of text messages ensued as the two boats poked across Florida Bay.  Andyman and Natedog did not like the look of things. They were going to hover around Zygote. They told Jeff to anchor up, hop onto their boat, and come back to finish after a rest on shore.  

Jeff eventually demonstrated the ballast issue, filling a tank by hand while Andyman held the bowsprit of Zygote on the stern of Bubbles Up. With a full tank, Zygote headed off like a bolting quarter-horse, but, alas, had to dump ballast to tack and resumed moving at a glacial pace.

So the two traveled as a caravan for a while, the sun slowly sinking in the west. At 8:45, as  Bubbles Up nipped through the cut at Toilet Seat pass, Zygote missed the cut and ran solidly aground.  Andy hopped off his boat and came over to help push Zygote off the bank, but to no avail.

​The tide was rushing out.

Like Max Smart says, "Missed it by THAT much."

On shore later, TwoBeers admits he suspected that his friends had deliberately put him on the hard.

They swear it was a mistake.

In any case, the options were few as the stars came out and the tide continued to ebb away. Jeff waved his friends along, left me a voice mail, got out his MRE and prepared for a hot meal before settling into his sleeping bag.

He was asleep before he could finish preparing his  "Beans and Chili."

At five, I woke to the muted ping of a message on my phone: Jeff was on the move.

It was only 8 miles or so from Toilet Seat to the finish.  I was really happy to punt on the variety of rescue mission measures I'd been cooking up with Jeff's bevy of friends:  Moresailesaid's call for Bob's inflatable to be deployed, Steve's offer to zip down to Marathon and maybe borrow a boat, DSea's suggestion of sailing one of the EC boats down to Toilet Seat and assess my favorite skipper's acuity, etc. etc.  

Meanwhile, Zygote was enjoying the light morning breeze, sliding northeast up the Florida Keys.  I tracked the little dot as it came through Baker Cut into Buttonwood sound, and then...kept going. Good lord, I thought, is he going to Gilbertson's for a breakfast burrito?  

I called him, and he answered, chipper as a cricket.  Hey babe, I said, are you going to tack?  
What, he said.
I can see you and you're going past the finish.
I'm coming up on marker —is it 92? I'm like 20 miles out. 
You aren't.
The boys said I was.
Well, I said, I promise you are not. Are you on starboard, with both blue sails up?
Ye-esss.
Okay, I'm looking RIGHT at you. You need to check over your shoulder at the black schooner and the big cell phone tower.
Pause.
​Oh, yeah. I'll be right there. 

Zygote landed at quarter after 8 on Wednesday, to a chorus of cheers and bleary fist-pumps.

​The assessment from nearly every finisher: this EC might have been the hardest one they remember. I concur. 

Thanks to everyone for the phone calls and messages of support and congratulations for Twobeers! It never fails to amaze me. We are fortunate beyond words. ​​