Of course I was at the wheel when the spinnaker halyard broke. Why is it that I always seem to be driving when things get, um, interesting? It’s an unanswerable question. Anyway, here’s what happened.

Aboard the sweet-sailing 57-footer Sky, under the command of one Johannes "Jopie" Helsen, the sun had risen after our second night at sea en route from Tampa Bay, Florida, to Isla Mujeres, Mexico, in the 50th running of the Regata del Sol al Sol, an international yacht race spanning the Gulf of Mexico. I'd been at the helm for about 40 minutes when, suddenly, in a rather fitful breeze at 0940, the kite's halyard parted and the sail fluttered into the sea, as soft and gently as if I were applying a crisp new sheet to a freshly made bed.

The very first thing that popped into my mind was, “This is great!”

I wasn’t kidding. I’ve watched a few spinnakers blow in my day, invariably on a black night in a rising wind in a rough seaway. Here, the waters were calm, the wind lightly astern, and our eight-person crew was wide awake, on deck and ready. If you had to drop a kite, it would be hard to imagine better conditions.

One of the handiest things to have on any sailboat, at any time — but especially in an emergency, large or small — is a skilled sailmaker. Luckily, we happened to have one handy: Dan "DJ" Driscoll, the Doyle Sails rep who'd built Sky's handsome set of brand-new sails. In a tone that was at the same time laid-back and urgent, he said, "Bear off." I was headed in that direction anyway, but his advice was reassuring.

It was a bit of a chore for the crew to gather the soaked sail back aboard — the spinnaker sock’s hoop, streaming astern, was a pretty effective sea anchor, and I had to luff head to wind to help them corral the sail — but the job was accomplished fairly quickly. And almost immediately, Jopie, Dan and the gang had a new chute on deck. Sheets and a fresh halyard were affixed, and it was hoisted aloft in no time flat.

“Nice job, bro,” I said to Dan, who had calmly orchestrated the whole maneuver. His shrug suggested next time we should give him something more difficult to do.

I’d glanced at my watch the moment the old kite hit the drink and did so again when the new one was up and drawing. Twenty-three minutes. Exactly. Hold that number.

Charlie Ball and Jopie Helsen
Fifty years ago, a pair of Florida kids raced together in the first Regata del Sol al Sol; a half century later, the now seasoned sea dogs, Charlie Ball and Jopie Helsen, were at it again.Chris Gourley, Caroline Southwell and Herb McCormick

Fifty years ago, in the spring of 1969, a pair of strapping, sailing-crazed lads from the St. Petersburg Yacht Club, Jopie Helsen and Charlie Ball, were ­crewmembers aboard an Ohlson 38 called Marespell, one of 15 entrants for the inaugural edition of the Regata del Sol al Sol. The event was initiated by the Mexican government as a means to promote tourism and the little island off Cancun called Isla Mujeres, at the time a sleepy fishing village with about a thousand residents and not a single paved road. “From the sun to the sun” was an appropriate name — after all, the sun rises over the starting line near St. Pete and sets over the finish near Cancun. Over the course of the race, the boys had quite an adventure, sailing through a fleet of Cuban fishing dories guarded by a looming gunboat; catching a glimpse of their first leopard ray; washing down beers that cost 18 cents apiece at the finish. Great memories all.

A half century later, on April 27 of this year, Jopie and Charlie were at it again, once more on the starting line for the race to Mexico. This time, naturally, things had changed. Instead of being mere deckhands, the old friends were the skipper/owner and navigator, respectively. The navigation itself was no longer by sextant and loran, but by sophisticated satellite-based instrumentation. And then there was the ride. Sky, to put it mildly, is no Ohlson 38.

Inaugural race map
A lot has changed in both St. Petersburg and Isla Mujeres since the inaugural race in 1969. But one thing hasn’t, which is the racecourse itself.Herb McCormick

No, the strapping 57-foot yacht, built in New Zealand at the vaunted Vaudrey Miller boatyard with a carbon rig and a lifting keel that drops down from 5 feet 6 inches to 11 feet 6 inches, among other features, is something altogether different. And ultimately, above and beyond Mexican races, so is its long-range mission. That’s because Jopie, with his girlfriend, Heidi Trilsch, is planning to sail it around the world.

Sky
With just two hours to go before the starting gun sounded, the scene on Sky was chaotic, with the boat's name and hailing port still being affixed to the transom.Chris Gourley, Caroline Southwell and Herb McCormick

Jopie says that, until very recently, the notion of circumnavigating never occurred to him. But it almost seems like his life’s journey led down such an inevitable road. Born in Holland to a boatbuilding father who moved the clan to Florida when Jopie was around 10, he started sailing at 5 or 6 and has fond recollections of puttering around his dad’s shop, fiddling with wood and model yachts he fashioned himself. By 13, after the family had settled in St. Petersburg, he decided to become a yacht designer and builder, and never changed his mind. In high school, he basically apprenticed with the legendary Charlie Morgan. He studied naval architecture at the Westlawn Institute, and by 25, ran his own boatbuilding company. Eventually, he tired of manufacturing and shifted his attention to yacht brokerage and his own high-end service and repair yard, Sailor’s Wharf in St. Pete, which has now been in operation for 40 years.

Starting on time
Somehow, we made it to the start on time, accompanied by our own spectator boat with the team from Sailor’s Wharf cheering us on. Jopie glanced over as we sailed on. It’s hard to surmise who was happier to bid the other farewell.Chris Gourley, Caroline Southwell and Herb McCormick

His interest in circling the globe was piqued when Sailor's Wharf did the refit for a client sailing in the World ARC Rally. After the customer returned, he regaled Jopie with stories and photos of his adventures in French Polynesia and beyond. Jopie was transfixed. A lifelong sailor, Heidi was also fascinated. One thing led to another, and a search for the right boat commenced. At first, Jopie had little interest in Sky, but he sailed it, then had a second look, then another. Something clicked. He saw the potential. It could definitely be the right tool for the job.

Linwood Gilbert
Linwood Gilbert was another veteran St. Pete sailor who’d sailed more than his fair share of miles and was steady on the helm. Though we’d never sailed together before, it took us little time to come together as a crew.Chris Gourley, Caroline Southwell and Herb McCormick

When Sky set out for Isla Mujeres after its own major refit, it was the first time its new sails were raised. The Regata del Sol al Sol was more than a boat race. It was the shakedown voyage.

Jopie
Skipper Jopie grew up sailing, knew from an early age that he wanted to become a naval architect and boatbuilder, and never wavered from that dream. Now, he’s looking forward to sailing around the world.Chris Gourley, Caroline Southwell and Herb McCormick

Just two hours before the starting gun was fired to begin that shakedown sail (and two days before our drama with the spinnaker), it seemed to me that our participation in the race was far from a foregone conclusion. An army of workers still scurried about the decks, screwing things down. The interior was in shambles, with brand-new cushions scattered everywhere, still in their plastic wrap. Aft, a worker had just affixed the name Sky to the transom in embossed letters, and another broke some bad news to Jopie, standing nearby.

“The S is upside down,” he said, gazing at the nameplate. Before stalking off, Jopie ­replied loudly, and in unprintable fashion.

The poor guy looked to me for solace. “Well, it is,” he said, sheepishly. For multiple reasons, I remained speechless.

But somehow, we made it to the start, over an hour’s motor from Sailor’s Wharf, with minutes to spare. I considered it nothing shy of a miracle. The trouble with owning a shipyard, Jopie later explained, is that all the customers’ boats come first. In any event, we were off.

Regata Amigos
One of the coolest traditions of the Regata del Sol al Sol is the Regata Amigos, when the St. Pete raceboats host some Isla residents for a day of racing.Chris Gourley, Caroline Southwell and Herb McCormick

To say that the roughly 450-nautical-mile Regata del Sol racecourse is interesting and challenging is an understatement. There are not one but three significant currents that must be addressed and compensated for, and doing so correctly (or not) holds the key to one’s success (or not) in the race. The circular, clockwise Loop Current in the middle of the Gulf is the first obstacle, but those who latch on to the southerly flowing east wall can enjoy a significant boost in the early going. Farther south, nearing Cuba, you must avoid, as best you can, the easterly flowing Gulf Stream, which can set you in the opposite direction from which you need to sail. Lastly, on the final approach, the northerly flowing Yucatan Current off the coast of Mexico can be dastardly if you find yourself too far north of Isla while crossing it. Happily, navigator Charlie had seen all this before, and he was ably assisted by yacht broker Josh McLean, of David Walters Yachts, an ex-Air Force man who knows his vectors.

In fact, the whole crew — which included another set of St. Pete sailors, Linwood Gilbert and Karen Park, as well as videographer Chris Gourley — was top notch. We’d never sailed together before, but I have to say we meshed quickly. It was a fun bunch.

With less than two hours to go before the start, Sky was in disarray, as an army of workers scurried about the decks screwing things down. It seemed to me our participation in the race was far from a foregone conclusion.

We enjoyed a good, clean start, and were soon accompanied by a big crew of workers from Sailor’s Wharf on a spectator boat, who were no doubt ecstatic and relieved to bid us farewell. Under Tampa Bay’s iconic Sunshine Skyway Bridge we went, beating to the one and only mark on the course, a channel buoy where a fleet of small-boat fishermen cursed and stamped as we slid past. Little did they know, there were another 29 yachts — the rest of the race fleet — still to come. Sorry, gents. See ya!

Dolphins
Once into the Gulf, for a long stretch we were escorted by a group of playful visitors frolicking in the bow wave.Chris Gourley, Caroline Southwell and Herb McCormick

Before long, the wind freed and we were able to set the spinnaker, reaching before a sweet 10- to 12-knot breeze under brilliantly sunny skies. Dolphins frolicked in the bow wave as we clicked along at a tidy 8.5 to 9 knots. It was Champagne sailing at its absolute very best. And it ­continued on through the night, with steady pressure and a nearly full moon illuminating the sparkling seas. The speedo was locked on 10 knots and even nudged upward in the puffs, with DJ notching the top number of 13.4 knots. The next day, 24 hours into it, we’d reeled off 209 nautical miles. Sweet.

With a northeast wind opposing a northbound current, which at times trucked along at nearly 5 knots, the going was downright nasty. Fast. But crazy. At the wheel, I discovered the best approach was not to look over your shoulder.

It lightened up as the day wore on, but we never doused the spinnaker. The second overnight sail was a little less sporty than the first. Lighter air meant we needed to sail deeper angles, and the breeze was up and down with small but persistent shifts. The level of concentration required at the wheel wasn’t commiserate with the results achieved; our speed hovered between 5 and 8 knots. But it wasn’t bad. The moon remained gleaming, and we were on our way to Mexico. It would’ve been rather churlish to complain.

Hours later, the halyard broke (we should’ve been adjusting it periodically to prevent chafe — oh well) and we had our brief but ultimately satisfactory fire drill. And lo and behold, there were only another 100 miles to go.

They were not easy ones. Actually, our last night at sea was pretty darn wild.

Sky's spacious cockpit
With its wide beam and twin wheels, Sky is simply a joy to drive, and there's plenty of room for crew work in its spacious cockpit.Chris Gourley, Caroline Southwell and Herb McCormick

Charlie and Josh had done a spectacular job navigating, hitting the currents precisely at every waypoint for maximum advantage. Just before sunset, they called for a jibe to head south early so we’d have a favorable slant on the Yucatan Current — we had to cross it sooner or later; there was no avoiding it. With a northeast wind opposing that northbound current, which at times trucked along at up to 4.7 knots, as verified by our B&G instruments, the going was downright nasty. Fast. But crazy.

Jopie Helsen
On his first visit to Isla Mujeres in 1969, Jopie Helsen made his way to the Mayan temple ruins on Punta Sur to record his presence for posterity.Courtesy of Jopie Helsen
Isla Mujeres
He retraced his tracks once again in 2018.Chris Gourley, Caroline Southwell and Herb McCormick

At the wheel, I soon realized it was best not to look over your shoulder, but sometimes I couldn't help myself. The scene was mightily impressive, with standing waves measuring 4 or 5 feet tall. But Sky handled them like an absolute champ, plowing ahead with purpose and dispatch, never rounding up, just tracking along under complete control with its twin rudders as if it were on rails. At one point, the tack line for the spinnaker stripped and the sail went flailing, but ­naturally, DJ was all over it, and it presented but a minor hiccup. We crossed the finish line, one end of which was the 90-foot Mexican navy ship Tulum, right around 0400. Only a pair of boats had already finished, one of which was the famous racer Merlin, the other a Tripp-designed 75-footer. Serious company. For a ­cruising boat on its first major test, Sky had acquitted itself nicely. The cold breakfast cervezas, followed by heaping plates of huevos rancheros, went down smoothly.

Merlin
With a full moon overhead shortly after crossing the finish line, we pulled into the customs dock and were greeted by the sight of the famous racing boat Merlin, one of only two yachts to complete the course before us. We were obviously in very good company.Chris Gourley, Caroline Southwell and Herb McCormick

Isla Mujeres is no longer a quiet village with a single hotel but a bustling island with two towns, 20,000 residents and countless day-tripping tourists from Cancun availing themselves of the many beaches and watering holes. We happily joined the festivities. We also welcomed a boatload of local kids and their families on board Sky for one of the event's traditions, the Regata Amigos. It was a great day.

On the night of the awards ceremony, Charlie and Jopie were justifiably recognized as competitors in both the first and 50th Regata del Sol, a happy and proud moment for both the longtime friends and their crewmates. And Jopie gladly accepted the prize for Sky's victory in our class. The shakedown trip could not have gone better.

Charlie and Jopie
Fittingly, at the awards ceremony, Charlie and Jopie hoisted some hardware. Yes, after all these years, the two friends are still making history together.Chris Gourley, Caroline Southwell and Herb McCormick

Well, except for one thing. When the handicaps were applied for the overall fleet prize, Sky finished second to a well-sailed Irwin 38, After You. Well done, guys.

But we couldn’t help chuckling at the ironic delta in corrected time between After You and Sky. Remember that broken spinnaker halyard story that begins this little tale? You guessed it. Sky finished second by precisely … 23 minutes.

Herb McCormick is CW’s executive editor. For more on the Regata del Sol al Sol, visit the event’s website.

The Regata del Sol al Sol has a fascinating history. It was founded by a local Isla Mujeres businessman named Jose de Jesus Lima (right), who wished to promote his home, at the time a sleepy fishing village. The Lima family continues to play a major role in the event today.

Jose de Jesus Lima
Regata del Sol al Sol founder Jose de Jesus LimaHerb McCormick

Way back when, the elder Lima was friends with Fidel Castro, who trained on the island before returning to Cuba and raising no end of rabble.

Souvenirs
Souvenirs from that era are still on display today.Chris Gourley, Caroline Southwell and Herb McCormick

Sky's Next Adventure

When Jopie Helsen and Heidi Trilsch set sail from St. Lucia on January 12, 2019, to begin the World ARC 2019-20, they will be doing so not only as a personal quest to sail around the world, but also for a cause. Jopie is a cancer survivor, and the couple have many friends and family members who have been affected by the disease. So their goal is to raise $1 million for the Leukemia and Lymphoma Society. A videographer, Chris Gourley, is part of Sky's crew, and the team plans on recording the voyage on YouTube and making their videos available to school kids for educational purposes and also for supporters of the adventure. For more details on how to follow the passage, or to make a contribution, visit Sky's website.