Anthony Vandenberg: enjoying the sunset during the 2021 WaterTribe Everglades Challenge | Photo: Vandenberg

A spell was cast on Anthony Vandenberg as he attempted to complete the 2021 WaterTribe Everglades Challenge. This time, blame it on the bull manatees.

"Bermuda Boy" once gave everything he had, but luck is not on his side.

The veteran marathon windsurfer will have to wait for 2022 to try and finish the 300-mile sailing adventure along the Florida coastline, from Fort De Soto's East Beach to Key Largo.

This year, he threw in the towel after only 101 miles of adventures and misadventures.

Here's what happened, in his own words.

Anthony Vandenberg: he rode three manatee in his 101-mile adventure along the coast of Florida | Photo: Vandenberg

Riding Manatees

Five minutes after leaving checkpoint one, I was already bronco-riding a big bull manatee in four feet of water.

The entire board came out of the water about three inches, but I managed to land it. "Once in a lifetime experience," or so I imagined.

As I reached Boca Grande, I was totally obliterated - everything I had worried about and much more was a reality.

I felt like the waves and gusts were treating me like a bowling pin.

I got knocked down so many times in that maelstrom washing machine that I could not even get the sail fully out of the water.

So I rode it out to leeward Gasparilla Island shore by sailing with just the tip of the sail pulled just above the waves by locking a portion of my uphaul into my harness hook and leaning back as hard as I could.

I was bruising the hell out of both thighs where the harness crushed thru to muscle down to the bones.

I got to shore, broke down the sail, secured it to the deck, and went into paddling mode.

Fifteen minutes later, I arrived at Hoagen Key Island camp, re-rigged the sail, pull the top reef out to reduce my sail area, and noticed - or thought I noticed - wind and waves had calmed down a bit.

Anthony Vandenberg: the marathon windsurfer hydrates before resuming sailing | Photo: Vandenberg

The Ultimate Physical Test

I got back on and executed a plan to cut over and across to the west side of Pine Island to get to flatter water.

This passage was the roughest in my entire sailing career, and quite a few times thought the exhaustion would do me in.

Once in the safety of the flat water shallows, I changed out to my six-inch shallow drafter fin - just a fin I chopped down to just under six inches - and sailed the entire length of Pine Island in less than one feet of water.

For quite a few miles, I was plowing a little one-inch deep channel in the mud and scratching flounders' backs.

It was really squirrely with the tail weaving the board with each gust.

It wasn't until a few hours later that I realize that by just tapering down the daggerboard just a pinch, I was able to reduce the weaving and saved my hips greatly from the torture.

I could never have survived sailing downwind 30 miles in the normal channel of the Sound (down Caya Costa, Captiva, and Sanibel Islands) with the open wind fetch and the choppy conditions.

There's no way my body could have taken that punishment, so I'm quite proud of the decision to cut across and risk being stuck forever somewhere in the mud on the west side of Pine Island.

It is really the only thing I feel any pride about.

As I blew past "Conchquistador" - an amazing participant who does the Everglades Challenge on a stand-up paddleboard - a few miles down from the entrance, I could not but help feel this was classic "The Tortoise and the Hare" by Aesop.

I knew this tortoise was going to destroy this foolish hare, so I forbade myself from feeling even a pinch of competitive satisfaction in passing another Triber.

Anthony Vandenberg: relaxing at a beach somewhere in Florida | Photo: Vandenberg

Pee Zipper: Open

I saw the sharks with dorsal and tail fins practicing for movie roles. I think I might have good footage of one on video as I chased him down a bit.

As I approached York Island, I noticed a sliver view of the skyline and Sanibel Causeway bridge between a gap in the mangroves and decided to cut thru.

As soon as I pointed up just a little, I realized immediately that little stub of a fin would not work for any angle but straight downwind.

So, I stopped in the lee of a little oyster bed to change back to my normal fin, jumped off the board, and felt icing cold water enter through the half-inch of the open gap of my pee port zipper.

I reckoned that I had not completely closed it earlier while sailing with only one hand on the boom and the other, not on the TV remote.

After putting back in my racing 21-inch race fin, I prayed with fervor that I would not get stuck behind York Island forever in her muck with the big Sanibel Causeway Bridge within view.

Just as I was making it out from behind York, I got in a wind shadow.

However, the current ninjaly drifted me out of the passage and placed me right atop a whole pod of manatees.

Once they realized I wasn't a cloud shadow, the surface of the water in about a 15 feet radius around me erupted like the nuclear testing in the Bikini Atoll.

The next moment, I was really bronco‐riding a giant bull manatee the sows call Hanker.

First, the bow came out of the water at least 2.5 feet, followed by the stern, and for the second time in my life, I was again bronco‐ing a bull manatee without a support clown.

I had just safely landed that ride and hadn't yet retightened up my hand grip on the boom when a second manatee blew up the 1⁄4 half aft portion of my board and drove my bow and dry back bag underwater all the way to the mast track.

This was my third and last manatee rodeo to date.

Bermuda Boy: checking his equipment before another windsurfing day | Photo: Vandenberg

The End Is the Beginning

Once out in clear wind, I had the best planing run from there, under the big bridge and right onto Fort Myers' North Beach.

Top speed on that run? 18 knots, with 90 percent of that run in the harness and straps and planing.

A bunch of windsurfers on the west side of the causeway looked at me like I was from outer space as I cut through their slalom field.

When I got on the beach, I looked at the forecast for multiple days and saw more too deep broad reaches, most probably right on the tail.

They were practically all squirrelly downwind tacks, so I threw in the towel like the super loser, quitter, crybaby - the real word I want to use would get me canceled - I wish I weren't.

It's been two days now, and I don't think there's been any stop in my brain second-guessing my cowardice and lack of willpower to push on.

I learned a few lessons and still ask myself a few questions.

What the hell was that southeast monster blast wind from just before Longboat Pass to about the mouth of Big Sarasota Bay?

Waiting to go outside until Nokomis Beach Park was a big mistake - I should have sailed out Sarasota New Pass.

I never went under so many bridges by holding onto just the harness lines and laying the sail forward at a 45-degree angle.

Juice, Iron Bob, and Greg must have a motor hidden somewhere onboard - someone should protest the race committee.

Finally, thanks to the lifeguard that, after serious deliberation about the safety of the swimmers, let me launch and sail across his beach into the Gulf with no swimmers or shell gatherers and the lonely three swim buoys.

Once again: thank you to my wonderful and beautiful wife for all her understanding, support, and love.

Top Stories

Professional surfers Kai Lenny and Jamie O'Brien embarked on a thrilling adventure when they set sail aboard the high-performance USA SailGP F50 foiling catamaran.

Planing is one of the most exciting skills you can master while windsurfing. It usually separates beginners from intermediate and advanced sailors. But what is the minimum wind speed to get flying over water?

Imagine gliding across a frozen lake, your sail catching the wind, and skis slicing through the ice and snow. Meet the sport that blends the thrill of windsurfing with the crisp, cold beauty of winter landscapes.

The Portuguese island of Madeira is home to the world's first natural swimming pool windsurfing regatta.