David Cook

As long as his Chrysler holds together, Ben Friberg and his four friends should reach Key West today. They'll unload bags of gear onto a chartered boat, shake hands with the captain and sometime this weekend, begin to sail 90 miles south to Havana, Cuba.

There, among the jazz and cigars, they'll wait.

And when the weather breaks and that perfect window of opportunity opens, Ben will take one goodbye step off a Cuban beach and onto his stand-up paddleboard (SUP) to attempt what he says no person has done before.

A nonstop SUP trip from the shores of Havana to Key West.

"Good conditions? 20 or 24 hours," he said Wednesday. "Worst-case scenario is 40-plus."

In 2011, a Miami lifeguard named Cynthia Aguilar made the trek, but did so prone -- on her knees, her hands paddling in the water, making that underwater silhouette perfect for "Jaws." She'd tried before, but was apparently undone by strong currents and Portuguese man-o'-war stings.

(Second time around, she wore long sleeves.)

Minus the moments when ocean swells and squalls might knock him down, or if the board underneath him wobbles him off during a lightning storm, Friberg, 35, will be standing the whole way. His board of choice is 14 feet long and 26 inches wide. His feet will face forward, and he'll paddle kind of like you do when you want to go really fast in a canoe: 10 strokes on his left side, 10 on the right.

Repeat, from Cuba to Florida.

"It is like a 90-mile gauntlet," he said. "A 90-mile obstacle course with Mother Nature."

Tropical storm Dorian is brewing in the Atlantic, and moving, ahem, dead-eye toward Cuba. Oddly, he's not that upset, as if the storm only adds an extra dose of hell-yes adrenaline to the trip.

"I'd rather there be some energy from Mother Nature," he said. "Makes it exciting."

Last summer, he SUP'ed farther than anyone's SUP'ed before: in 24 hours, 238 miles down Canada's Yukon River. Not long after Yukon, he started cooking up what he calls "the Cuba concept." He got the green light from Cuban officials, but only a few weeks ago did the permits and permission from Washington arrive.

"Nobody's done it before," he said.

Friberg picked his perfect crew: his dad, well-known funeral director Russell Friberg; Hunt Jennings, a local paddler who will kayak near Friberg, shuttling him food and drink (to-go packs of vanilla pudding and fresh blueberries are his favorites). A medic, navigator, boat captain, cook, journalist and two friends: Sam Silvey and Hugh Huffaker, of the digital marketing group Silvey + Huffaker Creative.

"It'll be a great story," said Silvey.

The two locally-known adventurers plan on documenting Friberg's journey with six cameras, including one mounted to a drone they'll pilot remotely from the boat.

They created www.cubasup.com, which will give live feeds from the adventure.

"If you see him going off in the wrong direction, you know a shark ate him," said Huffaker.

The rules: Friberg can't get aboard the chartered support boat. Can't draft off the kayaking Jennings. Won't paddle more than five strokes while sitting.

If Dorian blows heavy from the east, Friberg will have to paddle the entire journey from his left side.

Think he's nuts?

Somewhere out in the blue-cold waters between Canada and Greenland right now is an even crazier man named Bart de Zwart who's paddling from Canada to Greenland.

Unassisted.

Nobody else but him, his supplies and his SUP.

"Last night, he was probably sleeping on a piece of ice," Friberg said.

(If you've ever fought with your wife before bed, you may know the feeling.)

Because of storm Dorian, Friberg gives himself 50-50 odds on making it.

"So be it," he said. "We'll still be having fun."

Once again, an outdoor athlete from Chattanooga is making headlines and drawing attention to the treasure of outdoor wonderland opportunities here.

"Friberg is definitely pushing the limits of what kind of distances can be covered on a standup board ... if his past accomplishments are any indication, he'll set records for years to come," emailed Will Taylor, associate editor with SUP magazine.

So Ben, bon voyage. We'll be watching and cheering -- this journey, and all the ones to follow.

Contact David Cook at dcook@timesfreepress.com or 423-757-6329. Follow him on Facebook and Twitter at DavidCookTFP.