How Never Alone Won the Caribbean Regatta Championship

With Ross Nuechterlein on the helm and his father Paul on the rail, the race crew of the Cal 25 Never Alone from Detroit lead the fleet into Virgin Gorda Sound during the Helly Hansen Sailing World Regatta Series Caribbean Championship hosted by Sunsail. Simone Staff

His tan has long since faded, but Paul Nuechterlein still can’t get the smile off his face from that time when he, his son Ross, a crew of his best mates and a mothership catamaran full of rowdy racer-chasers won the regatta of their lives.

The regatta was, of course, the Helly Hansen Sailing World Regatta Series Championship in the British Virgin Islands. Months earlier, Nuechterlein and his friends on Never Alone had won their Cal 25 division at the series’ Detroit stop, which scored them a championship berth, a 42-foot bareboat monohull from Sunsail and six days of Caribbean vacation racing.

The unknowns they had to top for the title included Jeff Padnos’ S2 7.9 aces (K2) from Holland, Michigan; Craig Roehl’s Tartan 10 Meat entourage from Chicago; Carolyn Corbett and her Elektra squad of IOD and Viper 640 sailors from Marblehead; and Brad Tindall and Greg Turman’s J/105-racing Texans on TNT. Rounding out the fleet was veteran pro George Szabo from Quantum Sails San Diego. He had nine souls crammed onboard his vessel, three of them pre-teen girls.

.embed-container { position: relative; padding-bottom: 56.25%; height: 0; overflow: hidden; max-width: 100%; } .embed-container iframe, .embed-container object, .embed-container embed { position: absolute; top: 0; left: 0; width: 100%; height: 100%; }

K2, Meat, TNT and Never Alone were each sporting motherships laden with friends, so the flotilla was indeed a grand one when it set off from Sunsail’s base in Road Town, Tortola. The itinerary for the racers was simple: Day 1, race around a bunch of islands. Day 2, race to a resort. Day 3, enjoy a lay day at said resort. Day 4, race to a pool, a deserted island and then a dance floor. Day 5, sprint to another anchorage and then buoy race through its mooring field. It would all end with awards on the beach and cannonballs from the upper deck of the legendary Willy T.

That was the plan, and the crew of Never Alone was ready for it. Upon winning their berth back in June, they did what all good race teams do: recon. They got tips on how to locally source materials for a whisker pole, how to get maximum speed from their untunable bareboat and how to get around and through the BVI’s towering islands.

“There was a lot of information available to us to find out which islands we would be sailing to and how to trick out the boat a little bit,” says Ron Sherry the greatest American iceboat racer of our time and Never Alone’s all-purpose crewmember, “what we would need to bring to make our whisker pole and trimming aids and all that kind of stuff.”

George Szabo and Kevin Dumain get their Sunsail 42 into a groove after a challenging start against the BVI’s Sandy Cay. Dave Reed

They arrived in Tortola with a veritable chandlery of hardware, tools and ropes. And lo and behold, the planning immediately paid off. They had a decent start in the first race, a circumnavigation of the islands Cooper, Ginger and Salt, which at one point had them calling for water at reefs awash.

“We had to really hug the shore with the crashing waves and there were three boats all trying to get as close to those rocks as possible,” says Ross Nuechterlein, Never Alone’s captain for the week. “That was nerve wracking.”

Overlapped as they rounded the top of Ginger Island and turned downwind toward the finish, Never Alone’s preparation was on display. The 14-foot 2×4 they’d crafted into a whisker pole was working its magic, as was its handler, Ken Swetka. They had a sophisticated contraption with multiple handy-billies that gave them multidimensional control of the floppy jib’s profile.

The buoy racing portion in The Bight at Norman Island was ultimately a one-race dud, but Never Alone won that one too, and so, before shot-skis, jumps and another late night with their new friends on the Meat mothership, they were crowned Caribbean Champions. Dave Reed

They almost pipped Szabo and his team at the shortened finish.

“Another couple of hundred feet,” says trimmer Tom Dawson, “and we would have had them.”

The next morning, following a morning scramble through the boulders of The Baths—the BVI’s iconic natural wonder—the race committee dispatched the sailors and motherships to their second destination: The Bitter End Yacht Club.

Ken Swetka and Ron Sherry Wave racing. Simone Staff

In preparing for this leg, Sherry had called a friend who knew the area well, and his advice was well taken. “He said, ‘just look for the puffs and stay where the pressure is,’” Sherry says.

With another decent start, Never Alone’s navigator Tom Dawson nailed the layline to the first reef, then did the same to the next set of islands—skirting their 10-foot fathom—and then called a perfect layline into Virgin Gorda Sound from a million miles out.

Buoyed by their race win, they were intent on dominating the Hobie Wave racing at Bitter End YC (the race committee didn’t bother recording finishes), the Mount Gay Rum drink recipe contest (close, but no) and the SUP-tow surf challenge (maybe, but again “scoring issues” prevailed). Still they and the flotilla devoured all that Bitter End and Virgin Gorda offered for the lay day: snorkeling reefs, winging off the beach, windsurfing and nighttime tomfoolery.

The idle hours of the lay day, however, were torture for Szabo, who couldn’t put a finger on what was off with his boat. Naturally, he sought advice from the guy winning the regatta. It didn’t help.

Competitors enjoy a Bitter End YC lay day with Tom Dawson prepping for SUP towing. Simone Staff

“I was standing on the back of our boat at the dock and George was beside himself,” Nuechterlein recalls. “He came over and said, ‘You gotta help me out. There’s something wrong with our boat—the rudders don’t line up. They’re not parallel.’

“So, he then asks, ‘do you mind just going on your wheel and moving it back and forth?’

“I did while he was walking back and forth looking at my rudders. And then he finally says, “Hmm, yours don’t line up either.”

The Elektra crew cooling off with a cold one. Simone Staff

Never Alone carried their mojo straight into the next day’s race to the pit-stop pool at Scrub Island Resort and Marina. To get there, they had to short-tack their way out of Virgin Gorda Sound before weaving through more islands where they once again found themselves nip-and-tuck with Szabo and his family. The San Diegans got the win at Scrub, but Never Alone returned the favor with a runaway victory in afternoon’s second race to Sandy Cay.

With the overall results confirming the top three boats mere points apart, the championship’s final leg was a win-or-lose deal for the Detroiters. To win, they had to first navigate the current-and wind shift-riddled Great Thatch Cut. The Cut is divided by a tall island, so there were only two strategic choices: leave it to starboard and run the gauntlet or leave it to port and work the St. John’s shore.

The latter option rarely works, but Szabo went for it. As did Never Alone, the two of them split from the leaders as they entered the cut. Szabo, however, centered on the rhumb line too early while Never Alone kissed St. John’s and slam-dunked the fleet with truly astonishing upwind boatspeed.

They had their Sunsail 42 smoking. Having applied their own telltales to both the mainsail and the jib was crucial, as was their trimming technique and the use of their handy-billies.

TJ Valentor, of Chicago’s Tartan 10 Meat, is happy to do the whisker pole work on their Sunsail 42. Simone Staff

“The jib tracks on these boats are too far forward and too far inboard,” Swetka says. “It’s perfect for ergonomically walking around the boat with a bathing suit on, but it’s ridiculous for racing. So, when we were going upwind I always pulled the jib outboard and back a little bit.”

Ross Nuechterlein, alone at the helm, had his work cut out keeping the boat up to speed, but his Cal 25 skills were well applied.

“Anytime you start pinching with these boats, you just completely stop,” he says. “When you load them up to get moving out of a tack you can really feel the whole boat going sideways.”

The 2025 Caribbean Champions of Never Alone with the race and support crew, celebrating their win on Norman Island. Simone Staff

As a first-time helmsman of a 42-foot charter boat, he adds, it was especially good having his wife Karly in the middle. “On the Cal, you have two people behind you and one person right in front of you so you can hear what everyone’s saying,” he says. “But not on this boat, so it was great to have her there funneling information to me about what’s going on at the front of the boat.”

The buoy racing portion in The Bight at Norman Island was ultimately a one-race dud, but Never Alone won that one too, and so, before shot-skis, jumps and another late night with their new friends on the Meat mothership, they were crowned Caribbean Champions. And there, on the sands of Norman Island, emerged the mile-long smile that is stuck on Nuechterlein’s face.

The post How Never Alone Won the Caribbean Regatta Championship appeared first on Sailing World.