SINT MAARTEN (SIMPSON BAY) - The legendary Around the Island Race returned in spectacular fashion on Day 2 of the St. Maarten Heineken Regatta, delivering thrilling tactics, high speeds, and unforgettable moments on the water. Sailors were greeted with another near-perfect Caribbean race day, as steady trade winds held between 18-20+ knots under clear skies, setting the stage for one of the most iconic races of the regatta.
The action began with a dramatic and highly anticipated start in Simpson Bay, where the entire fleet of more than 100 boats gathered around a single start line. Crews circled patiently in the breeze as they waited for their class start times, creating a spectacular sight for spectators. One by one, the classes charged off the start line toward the first windward mark before heading offshore to begin their lap around the island.
Race Committee placed the opening mark strategically, forcing teams to think carefully about positioning and tactics from the very first leg. With shifting winds, tight boat traffic, and some superyachts, the first upwind stretch proved tricky.
In CSA6, Maëlia was the first to round the windward mark, with SAILBOATSURVEY Blueprint just inches behind. More Zessin’ followed closely and executed one of the fastest spinnaker hoists in the fleet immediately after clearing the mark.
As the race unfolded around the island, SAILBOATSURVEY Blueprint ultimately claimed first place in the class, while More Zessin’ climbed into second thanks to strong downwind maneuvering. Maëlia secured third place in the tightly matched fleet. “Our boat tends to do well with pressure,” said the crew of More Zessin’, who now hold the overall lead in their class after two days of racing.
For many teams, the biggest tactical question came immediately after the first mark rounding: whether to set a flying sail early or hold off on a tricky heading. Some boats committed quickly, while others waited for more stable angles as they made their way around the island.
The Melges 24 fleet opted for an aggressive tactical play, sailing high to windward after the first mark to find clear breeze before blasting down on a fast reach above the fleet and setting their spinnakers. Meanwhile, many other teams held lower angles until clearing the next mark before deploying their kites.
The powerful conditions produced plenty of dramatic moments, including several boats becoming overpowered on the downwind legs. Morpheus struggled to control their A2 spinnaker at one stage as the breeze built, highlighting just how demanding the conditions were.
In CSA2, tensions ran high as RE/MAX ONE and La Loévie battled closely for position near the first mark. After rounding, RE/MAX ONE unexpectedly headed upwind while La Loévie continued on course toward the mark, bringing the boats within inches of each other.
“The racing is a lot of fun here,” said the crew of RE/MAX ONE, representing Italy and Portugal. “We loved being able to catch up to the fleets ahead of us, it made it very motivating.”
In CSA1, Team JAJO rounded the first mark in the lead and held strong pace around the island. But by the finish it was Privateer, the Cookson 50 from the United States, who once again secured victory in the class. Despite being the smallest boat in CSA1, Privateer has proven exceptionally fast and consistent, maintaining a perfect winning streak across the regatta’s races so far. The smallest boat is far from the slowest.
After several hours of anticipation in Simpson Bay, boats finally began appearing on the horizon as they rounded the cliffs at Pointe Blanche and headed past the Port of St. Maarten.
It was SOPHIA who first crossed the line, finishing with an elapsed time of 2:24:37. The next boat to finish was the Diam 24 pyratz gourmet sailing, clocking in at 2:53:35. While no course records were broken today, teams demonstrated strong racing capabilities in the windy and wavy conditions.
While many teams enjoyed strong performances, the demanding conditions proved too much for a few competitors. Team Island Water World was unable to start due to mast issues, while several teams retired. VANTANERA suffered a mainsail tear mid-race and was forced to limp back toward Simpson Bay.
Day 2 of the Regatta highlighted one of the event’s key values, inclusivity. The second annual Sailability Speed Race was held at the Sint Maarten Yacht Club. Sailors with disabilities were given the opportunity to experience their own regatta moment.
During the Speed Race, participants navigated their own timed course and became part of the wider regatta celebrations. The Yacht Club hosts a range of accessible sailing programs through its Sailability initiative, which provides opportunities for young adults with disabilities to experience the freedom of sailing.
Inclusivity can also be found across the racing fleet this year. “We have been working on a racing campaign for five years,” said skipper Yves Grosjean from team AFAZIK IMPULSE (NEOJIVARO) in France. “We’re racing in regattas around the world to raise awareness about aphasia, a language disorder caused by brain injury or stroke, and hope to expand the campaign even further.”
Another team representing Community Sailing of Colorado is chartering a boat for the regatta, bringing a crew dedicated to expanding access to sailing. “We’re a non-profit sailing school trying to bring access to the water,” said crew member Angelina Norris. “Our entire crew is volunteers and community members, this is a learning experience for many of us.”
Inclusivity even extends to the unexpected — including a four-legged crew member racing aboard Ilios, proving that the spirit of the regatta truly welcomes everyone.
After an epic day on the water, sailors and visitors gathered once again at the Port de Plaisance Regatta Village, which opened at 4 PM with free entry for the public. Following prize giving on the Fountain Stage at 6 PM, the evening came alive with Soca and Bouyon rhythms from regional performers including Ebony Empress, Wahyné, CIIO the Artist, Lyte, DJ King Kembe, DJ Siw’Roo, KRG Band, DJ Drino, Fire Coral and more.
With two days of racing complete, the competition is heating up and the fleet now looks ahead to another exciting chapter of racing.
Day 3 promises even more unforgettable action — and plenty more #SeriousFun!
Fleets converged at a busy and action-packed first windward mark during the Around the Island Race, shortly after starting in Simpson Bay © Laurens Morel
More Zessin' in CSA6 delivered strong downwind lefs to finish second in their class today, maintaining their overall lead © Laurens Morel
SOPHIA was the first to cross the line in the Around the Island Race with a time 2:24:37 © Laurens Morel
Sailors and locals alike jammed out at the Regatta Village to an incredible variety of local acts © Digital Island
