Dr. Jim Sears and his teammates sealed their fate at Monkey Point. As the countdown timer ticked to its final minute and the whistle blew, the doctor's Team Viper got antsy. In agonizing slow motion, the white bow of the Sears' Sunsail 41 — with sails eased to their stopper knots — broke the starting line early. When the race committee hailed his bow number, 69, the doctor winced in the shadow of his signature lucky straw hat. He knew then and there his four-year reign over the Helly Hansen NOOD Caribbean Championship was crumbling.

The team to leeward, strategically maneuvering to claim the doctor’s title, was led by its skipper Joel White, the tall, white haired and jovial general contractor from Marblehead, Massachusetts. White and his teammates on Juhnksho Bob knew they had the doctor right where they wanted him.

Team Juhnksho Bob
Team Juhnksho Bob, with Kirk Leslie at the helm, fine tunes the trim of its Sunsail 41 at the Helly Hansen NOOD Caribbean Championship’s leg from Sandy Cay to Norman Island. Several hours later they would win the leg and seal their championship win.Dave Reed/Sailing World

The two teams have been friendly rivals since the last time they faced each other in the NOOD Regatta’s British Virgin Islands championship in 2015. That year, Sears won the regatta on the final day, but White and Co., were the only team to beat them. They vowed to someday return to try again.

There, at the starting line off Monkey Point, White and his teammates surged forward in the waning seconds of the countdown and were caught over early as well. “I knew we were over,” White would later confess (although his bowman and co-skipper John Caunter naturally disagreed). “When we heard our number, it was like, ‘Uh oh,’ and then we heard Jim’s number called, and we were like, ‘Well, that’ll help!’”

While the rest of the fleet sailed away, the two crews stirred into action, trimming sails as their boats returned to the starting line in unison. White’s squad was a fraction quicker getting out of jail, their sails grabbing a sliver of the light southeasterly breeze. They ghosted away toward the finish at Sandy Cay, 12 miles or so directly downwind, while Sears’ sails drew limp and his proverbial wheels spun in the blue Caribbean Sea.

“We just couldn’t get it going,” the Doctor later lamented. “We were stuck.”

Jim Sears
Three-time winning skipper Jim Sears (at right) celebrates the team’s leg win from The Baths to Leverick Bay, their second leg win of the regatta.Dave Reed/Sailing World

After two hours of agonizingly slow downwind sailing along the picturesque and rugged northern face of Tortola, the Juhnksho crew clawed back through the fleet to earn their second consecutive leg win, but more importantly, they finally flipped the leaderboard in their favor. Overnight, as the seven raceboats scattered into the harbors and beach bars of Jost Van Dyke, the regatta had a new leader. With one leg remaining to be contested and only a single point between the two of them, the stage was set for a fitting and final-day battle into the Bight at Norman Island.

Sears’ crew was a collection of Southern California sailing buddies. He earned his first invitation to the Helly Hansen NOOD Caribbean Championship in 2014 after winning the San Diego NOOD’s overall honors with his Viper 640 FNG. He’s a pediatrician, a TV doctor, a health-food nut, and at this year’s BVI championship he was also the pied piper of a 19-person, three-boat entourage. Sunsail provided the raceboat for his defense and Sears organized one Sunsail catamaran mothership and a 50-foot Moorings power cat provisioned to the bilges with beer and sugar cane rocket fuel.

Jeremy Wilmot and Holley Toppa
Jeremy Wilmot and Holley Toppa, competing as a doublehanded crew, explore The Baths with regatta special guests, Volvo Ocean Race skipper Charlie Enright and his family.Dave Reed/Sailing World

White and his first mate, John Caunter, have been Marblehead buddies since high school, and in Massachusetts parlance, “They’re wicked good sailors,” too. Third man in the cockpit was their close friend Kirk Leslie, from Vancouver, and three of them swapped helming duties throughout the regatta. On the rail and assisting with sail trim were their three wives, Betsy, Katie, and Annabelle, respectively. They had no mothership to store their gear and food, but they did have dive tanks, which Caunter put to good use before the first leg around the Channels Islands that line Sir Francis Drake Channel.

In Cooper Island’s Manchineel Bay, the three old friends were seen carving away months of marine growth from their boat’s bottom, using the boat’s steel spatula to chip off the hard bits. This time, they were clearly in it to win it — for bragging rights back home at Maddie’s Sail Loft and a free charter to defend at the 2019 championship regatta.

The roster for this year’s fleet of 41-footers also included Chicago-based Tartan 10 skippers John Schellenbach and Amy Cermack and J/80 skippers Thomas Kopp, of Michigan, and Conor Hayes, of New Hampshire. Competing as a doublehanded entry (representing San Diego NOOD overall winner Argyle Campbell) was professional sailor Jeremy Wilmot and his first mate, Holley Toppa. As bonus surprise for competitors, Sunsail ambassadors and two-time Volvo Ocean Race skippers Charlie Enright and Mark Towill joined the armada with their families and spouses on a charter cat, providing expert advice to anyone who asked.

Tartan 10 skipper John Schellenbach
Tartan 10 skipper John Schellenbach, of Chicago, finishes Leg 2 of the Helly Hansen NOOD Regatta in Leverick Bay. Schellenback came on strong as the regatta progressed to finish third overall.Dave Reed/Sailing World

The five-day itinerary of inter-island races kicked off with a circumnavigation of the BVI’s smaller Channel Islands: Ginger, Cooper and Salt, all left to starboard. White and Sears wasted no time locking horns in the prestart, but White got the better start. The two of them swapped the lead several times, but Sears eventually won the first round soundly.

Still, the crew from Marblehead were feeling confident, hinting at better speed upwind. Once they could figure out the best downwind angles, said Caunter, they would have the total speed package and the means to dethrone the champ.

The following day, after a morning excursion into the unique boulder fields of The Baths, the race committee dispatched the fleet on Leg 2, from the Baths mooring field to a finish line set inside Virgin Gorda Sound, at Leverick Bay. Again, the opposite-coast rivals engaged in the pre-start, never once letting the other get out of reach. Eventually, after three hours of sailing, they would enter the harbor 1-2, with the rest of the fleet minutes behind. Team Viper was first across and Caribbean NOOD rout appeared to be in the making.

That was until White and Co., outfoxed their rivals in the pre-start of Leg 3, a 14-miler from Virgin Gorda to Anegada, with a lap inside Gorda Sound. White started perfectly, tacked to port off the line the first chance he got and Sears soon mimicked the tack. The maneuver was rushed, however, and the lazy jib sheet snagged a jib lead, causing the jib to flap in the wind until they sorted the snag.

In one-design sailing, mistakes do compound, and this was an unlucky and rare hiccup for Sears’ crack crew. Juhnksho breezed away untouched until the race committee cheered him across the finish line outside the entrance to Anegada. It was Juhnksho’s first leg win, and the first picket of more to come in their scoreline. Sears was second and Wilmot third, the later crossing the line with a beer in one-hand and his mate in the other, leaving the driving to his autopilot.

Amy Cermack
Tartan 10 winner Amy Cermack, of Chicago, gets a clean start from Cooper Island at the start of Leg 1, a circumnavigation of the British Virgin Island’s Channel Islands.Dave Reed/Sailing World

A lay day at Anegada was a welcome respite for all, a chance to explore the island’s wonders: from the flamingos and endangered iguanas, to the five-star beaches and snorkeling reefs that string the low-lying island’s northern shoreline. At the self-serve bar at Cow’s Wreck Bay, Sears gave no sign of rattled nerves. He was confident he could beat the all-couples team from Marblehead, if only he could stop making simple, avoidable mistakes.

A glassy sea greeted racers in Anegada for the 24-mile or so downwind leg to Jost Van Dyke, so the race committee led the fleet to a rendezvous at Monkey Point on Mosquito Island to wait for wind. When it started, as mentioned before, Sears’s team Viper shot itself in the boat shoe, and try as they might, there was no getting past the six-some from Marblehead. Sears and his band of merrymakers nursed their egos well into the evening at the Soggy Dollar while their rivals on bow Zero-Zero turned in relatively early.

Paddleboard race
Competition was as fierce on paddleboards as it was on the Sunsail 41s. Victory went to Team Viper with a impressive performance by team member Bob Hill.Dave Reed/Sailing World

Fresh and eager to clinch their NOOD victory on the final leg before the Norman Island In-Port Race, White and his teammates were first out of the anchorage and first to the starting line off the post-card islet of Sandy Cay where they waited on a day mooring and gave one quick buff to the boat’s pocked bottom. They also did a recon mission to the reef on the north side of the island, a piece of pre-race prep that would some come into play.

The protagonists engaged in the pre-start once more, and this time Sears started with the upper hand. White was buried in the second row, wallowing in bad air, hemorrhaging critical places as the fleet finally crossed the line. There was a moment of salvation, however, when Sears was unable to easily fetch the pin and slowly luffed to pass over with inches to spare. When Sears reached off to build speed, White’s lane opened up and with the patience of Saint Theresa, they waited for their first opportunity to tack. A precision layline call needled them through coral heads mere feet from the island.

Conor Hayes
Conor Hayes, of New Hampshire, preps his team’s mothership. Hayes’ family and friends, J/80 sailors, started the regatta with an OCS, but improved as the week went on, to finish fourth overall.Dave Reed/Sailing World

Once around Sandy Cay, the fleet endured in a slog of a downwind parade, led by John Schellenbach, before entering the notorious, current-riddled Great Thatch Cut at the western end of Tortola. Schellenbach got through unscathed, as did White, but Sears got swallowed by a swirling eddy of seaweed and wallowed with sails luffing or backwinded until the Kraken released him. There would be no comeback and the speed of the Marblehead crew was enough to promptly get past Schellenbach. They were moored and snorkeling before the next boat would finish.

final in-port race in the Bight on Norman Island
For the one and final in-port race in the Bight on Norman Island, doublehanders Jeremy Wilmot and Holley Toppa recruited Charlie Enright and Mark and Tahnee Towill. The team led for most of the double windward/leeward before being overtaken on the final jibe by regatta winner Team Juhnksho Bob.Dave Reed/Sailing World

All that was left was the in-port race, a one-shot, two-lap windward leeward inside the virtually empty anchorage of The Bight. Holley Toppa, on the helm, assisted by Wilmot, Enright and Mr. and Mrs. Towill, nailed their perfectly timed port-tack start by sailing around the backside of a four-boat pile-up at the pin and were off and running, chased by … you guessed it, White and Co., this time with John Caunter at the wheel.

2018 Helly Hansen Caribbean NOOD Championship crew
The 2018 Helly Hansen Caribbean NOOD Championship crew (l to r): Joel and Betsy White, John and Katie Counter, and Annabelle and Kirk Leslie.Dave Reed/Sailing World

With slick boathandling, the regatta leaders ground down the all-pro team until passing them on the final run to the finish. Sears, one of those caught tangled at the pin, posted his worst finish of the regatta (a fifth) and slinked over the line, mentally exhausted, but relieved the pressure of another defense had been lifted.

“The ironic thing is, my straw blew off my head right after the race started,” said Sears at the awards party ashore later that evening. “The thing was so beat up, with wires sticking out of it so badly I was bound to poke my eye out one of these days. But the guys insisted I wear it for luck. After the race, while we were motoring over to the Indians to snorkel, we found it, did a circle around it, and then decided it was a sign. It was time to let it go.”

Like the America’s Cup, victory can be both a blessing and a curse. White and his Juhnksho crew now have one year to organize their defense, their mothership, and all the planning that goes into an unrivaled week of racing in the British Virgin Islands. Sears, now the unofficial challenger of record, has vowed to return, with a smaller entourage and without the target on his back.