Day two of the highly anticipated 2026 Antigua Sailing Week brought a dramatic shift in wind and sea conditions, as hundreds of competing sailing vessels prepared to leave the sheltered Caribbean Sea and push north into the expansive open Atlantic. After anchoring overnight at Green Island South, crews spent the early morning prepping their yachts, framed by rolling hillsides dotted with blooming dagger log agave — Antigua’s national flower, a rare sight that only blooms for a handful of days once every two decades.
One by one, crews hoisted their sails and navigated to the official start line, where an 8-knot downwind breeze greeted the fleet. ASW Race Officer Chris Mansfield highlighted the strategic importance of early positioning for competitors. “The boats that really focused during the light air start and worked hard to get themselves into position were the best suited when the wind filled in,” Mansfield explained. “Being in the right place when that happened was crucial.”
As wind speeds steadily climbed, a powerful north swell generated strong shifting currents that tested sailors as they traced Antigua’s rugged northeastern coastline. For many racers, the unpredictable conditions made for a far more engaging challenge than the opening day of the event. “It was very different from yesterday. Lots of varying conditions to contend with, which made it a fun challenge,” said Dean Krocken, trimmer aboard *Kali*, whose crew secured back-to-back first-place finishes in CSA Class 1 on day two. “We put the spinnaker up and did four jibes or five into the finish.”
Tight, neck-and-neck competition played out across every racing division as the afternoon unfolded. Mid-race conditions proved perfectly suited for reaching and downwind maneuvers, with a steady 15-knot breeze rewarding crews that could balance blistering speed with precise boat control. “Today was quite challenging because we’re used to upwind starts,” said Pieter Hooft, headsail trimmer aboard *Contigo – Team HI 1*, the CSA Class 2 winner. Hooft and his teammates traded the lead with *Vildiur* for the first 6 miles of the course, which ran between Man o’ War Point and Devil’s Bridge, before pulling ahead near Guinea Island.
Hooft explained the unorthodox tactic that gave his Dutch team the winning edge: “We sailed zeeuwe-meisjes (wing-on-wing), and the drag from the current actually gave us an advantage. The opposing flow of water across the hull created just enough of an increase in apparent wind for us to pull ahead.”
Beyond the competitive racing divisions, cruising sailors participating in the event’s coastal rally took full advantage of the steady breeze and lively sea conditions, while also joining in Antigua Sailing Week’s popular Daily Treasure Hunt. Over the first two days of the event, participating crews have shared photos of their on-water adventures, ranging from group shots snapped in their official English Harbour Rum hats to surprise sea turtle sightings and stops at historic island landmarks. “The treasure hunt was a blast!” said Rob “The Dawn” Britts, sailing aboard *Mystic Lee*. “The whole day turned into an adventure.”
Once crews reached the day’s destination at Little Jumby, racers and cruisers gathered at The Hut to trade stories from the course before joining a lighthearted beach relay that mixed competitive and casual participants. Teams competed in a multi-stage challenge: speed-walking while balancing a lime on a spoon, a swim out to the local mooring field and back, and a final dinghy sprint around a marked course to the finish line. In a dramatic last-minute turnaround, the crew of *Impala*, who had trailed *Kiss Cool* through the first three stages of the relay, edged past their opponents to claim first place in the final seconds of the dinghy race.
As the sun dipped below the Caribbean horizon, post-race festivities moved from the beach into The Hut’s restaurant. DJ York got the crowd moving, and the dance floor stayed packed as crews partied late into the night, capping off a full day of on-water and onshore fun.
With two days of racing and adventure complete, Antigua Sailing Week 2026 continues to deliver world-class sailing, vibrant Caribbean culture, stunning natural scenery and shared camaraderie for participants from across the globe, both on and off the water. As the event moves toward Saturday’s leg from Jumby Bay to Ffryes Beach, Mansfield says sailors can look forward to a new perspective on Antigua’s iconic coastline and world-renowned sailing conditions.
“The beauty of this format is that every day feels different,” Mansfield said. “Different wind, different seas, different views – but the same spirit of competition and community.” Full race results are available online via the official event portal.