Skip to main content

Sailors take on the "Ultimate Challenge"

Florida circumnavigation adventure pits competitors against 10-foot Gulf waves and 1,200 miles

Florida circumnavigation adventure pits competitors against 10-foot Gulf waves and 1,200 miles

Wizard, as he is known among the paddlers, finessed his 12-foot sailboat 1,200 miles around Florida — sailing most of the way, sculling some and portaging his 180-pound mini-cruiser 40 miles across north Florida — to win the sailing division in the Ultimate Florida Challenge.

Wizard, aka Matt Layden, a draftsman for a megayacht design firm in Jensen Beach, Fla., is one of the WaterTribe (, a community of small-boat sailors and paddlers who test themselves on adventure challenges. WaterTribe’s March 4 - April 2 ultimate challenge — circumnavigating Florida — drew 10 challengers in this year’s first running. Seven finished, among them Layden, who posted a time of 19 days, 12 hours, 55 minutes — six hours behind super-paddler Warren Richey, a Christian Science Monitor reporter from Plantation, Fla.

Layden, who has designed some innovative kayaks and won the 300-mile Everglades Challenge in a sailing kayak of his own design in 2003, says he much prefers sailing the challenge to paddling it.

“You don’t have to work as hard,” says 44-year-old Layden, who is known for his designs of do-it-yourself shoal-draft “microcruisers.” Enigma — so-named because people ask him, “What is it?” and he replies, “An enigma” — is his own creation. Twelve feet long, shoal draft, with a 56-square-foot lugsail, Enigma is a sailboat — not a kayak — built of glassed-over plywood. It is beamy with a high freeboard, covered cockpit and two add-on wheels for portaging. Layden calls it a “small, light, portable, go-anywhere cruising boat.”

He’s not kidding about that. The ultimate challenge took him on a loop around Florida from Fort Desoto on Tampa Bay down the Gulf of Mexico to Key Largo, and through the Straits of Florida to the East Coast. He sailed up the coast to the Georgia border, then up the St. Mary’s River to Fargo, Ga., where he portaged Enigma 40 miles along a busy country road to the Suwannee River. Back in the water, he sailed Enigma downriver to the Gulf and on to Fort Desoto — in less than 20 days.

“It’s a fun thing,” says Layden, this from a boatman who likes to sail little boats nonstop for days at a time while thriving on catnaps, even when he cruises. He has cruised the East Coast extensively, to Maine, around Florida and to the Bahamas. For the ultimate challenge, he sailed literally 24-7 part of the way because when winds are good, “You just keep going,” he says. “I’d rather be under way than stopped at the dock or exploring a town. That’s just a personal preference.”

Winds were generally favorable during the challenge — pushing him an average of 3-1/2 knots over much of the course, but when winds weren’t good he deployed a “yuloh,” a Chinese sculling oar that extends from the stern and propels the boat when the skipper sweeps it back and forth.

The Coast Guard, suspecting Layden might be a Cuban rafter sneaking in on a sophisticated home-built boat, stopped him off Miami. Once satisfied that he was racing and not emigrating, they made him check in by cell phone each hour because they were worried that such a small boat might sink in such big swells, according to Layden’s log blog. Tired of maintaining this cell phone umbilical cord, Layden cut into the Intracoastal Waterway at Hillsboro Inlet and sailed much of the way up Florida’s east coast on the ICW and the broad Indian River Lagoon.

Enigma and its supplies weighed in at about 300 pounds by the time Layden reached Fargo for the portage. Aside from a flat tire, which he repaired, the portage was uneventful and not as hard it sounds.

“Once you get up to speed, it goes right along,” he says.

The top three finishers arrived at Fort Desoto within six hours of each other. The next boat crossed the finish seven days later; others took 29-1/2 days to complete the 1,200-mile course. “It was a very, very close race,” says Steve Isaac, WaterTribe’s “chief,” which is his race name, too. “Any one of those three could have won it. They were neck-and-neck coming down the Suwanee River.”

Isaac, 57, of Clearwater, Fla., founded WaterTribe five years ago with the first running of the annual Everglades Challenge from Tampa Bay to Key Largo. Isaac — a self-employed software engineer who is married and has a child — said he found the inspiration for the Everglades Challenge in the Eco-Challenge, an adventure race started by Mark Burnett, producer of TV’s “Survivor” series, and in the French Raid adventure races. Both send challengers through deserts, jungles and mountains, and test their skills in mountain-climbing, kayaking, skiing, hiking, motorbiking, mountain cycling and other disciplines.

“I always wanted to be an adventurer,” says Isaac. “But I’ve got a wife and a kid and responsibilities. I didn’t feel that I could chuck all that and go adventuring.” A kayaker for 25 years, Isaac started thinking about an adventure he could pursue. “Why not do adventure races for kayakers?” he wondered. The Florida challenges are completed in a couple of weeks instead of several months, and cost $1,500 or less in entry fees instead of $50,000. Challengers who choose to do only part of the ultimate challenge pay $295 a leg.

Isaac still is reluctant to call WaterTribe’s events “races.” He prefers to call them “adventures” or “expeditionary adventures” because they are more personal challenges than cut-throat competitions. Isaac does set a time limit for the ultimate challenge of a little over 29 days, and seven days for four of the five legs. “That makes it an adventure,” he says. “Anyone can paddle from Tampa Bay to Key Largo — given enough time. What makes it a challenge is putting a time limit on it.”

The adventures draw all kinds of challengers. Sixty-five crewmembers paddling or sailing 55 boats — some of them doublehanders — turned out for the 2006 challenge. Thirty-six boats entered the first leg to Key Largo; 10 raced around Florida; and the rest raced a marathon from Fort Desoto to Boca Grande on Florida’s west coast.

“We have doctors, veterinarians, professors, nurses,” Isaac says. Most are active people at the “upper end of the income scale” who have the vacation and flexibility to do a challenge, and the money to buy a boat and assemble all the survival gear required to enter a challenge.

“It’s something exciting and challenging, not only physically but mentally,” Isaac says. “It does strike a chord with people.”

They can tailor their adventure to their own challenge level.

Top finishers in the Everglades Challenge arrive in 2-1/2 days and paddle pretty much 24-7. “They know the rule by heart,” Isaac says: “Keep paddling while the weather’s good. Don’t stop until you have to.”

Rules are flexible. Some entrants brought folding bicycles for pulling their boats overland on wheels. Two wore in-line skates for the portage and harnessed themselves to their kayaks. Isaac thinks he’ll have to ban the skates next time (the ultimate challenge is a biennial race, the Everglades annual) because they are too dangerous when skippers have to jump on and off the shoulder to avoid traffic.

There are no boat size limits, but several requirements impose a practical limit. Crewmembers must be able to drag their boats off the beach and into the water in a LeMans-type start. Masts must be unstepped to get under a very low bridge at the first checkpoint. The boats also must fit between two bridge abutments 10 feet apart at that checkpoint, which limits the size of multihulls that can enter.

Challenger’s race in four classes: expedition kayaks and canoes with or without downwind sails up to 1 square meter; racing kayaks and canoes with no sail permitted; expedition kayaks and canoes retrofitted with an upwind sailing rig; and an open and experimental class for craft using any kind of wind or human propulsion. Enigma was in this last class, as were some Hobie Cats and other multihulls.

Does paddling in sunny Florida compare as a challenge with trekking across Alaska tundra or Sahara desert? Isaac says the Gulf can kick up to 10 feet when a cold front comes through from the northwest. That and the time limits make this race “very, very tough.

“I tell people this race is not about paddling speed,” Isaac says. “It’s about mental toughness. You have to keep going, even in bad weather. Believe me, it’s a different world 10 miles offshore when you’re by yourself, it’s dark outside and you’re out of cell phone range. You have to cover 50 miles a day to make the time limit.”

A California couple — seasoned adventure racers — paddled the ultimate challenge in a kayak and found it as rigorous as it gets.

“They said, ‘This is the hardest race we’ve ever done,’ “ Isaac says. “And they’d just finished a 100-mile snowshoe race through Alaska.”