The Montego Bay Yacht Club is pleased to announce the return of the Pineapple Cup–Montego Bay Race, with the 36th edition of the iconic Miami-to-Montego Bay offshore race scheduled to start April 10, 2027, hosted by Biscayne Bay Yacht Club. The event will be recognized as US Sailing’s US Open – Offshore, marking an exciting new chapter for one of the Western Hemisphere’s most celebrated ocean races.
First contested in 1961, the Pineapple Cup has earned its place among the great challenges in offshore sailing. The approximately 811-nautical-mile course takes competitors from Miami across the Gulf Stream, along the Bahamas, past Cuba and through the Windward Passage before the final approach to Montego Bay, Jamaica. The race demands expert navigation, strategic weather decisions, careful boat preparation and the endurance required to compete offshore.
The 2027 edition represents an important milestone for the event, bringing together the Pineapple Cup’s storied history and US Sailing’s support for the continued growth of offshore racing. Full race requirements, eligibility criteria, safety requirements and official details are available in the Notice of Race.
“There are ocean races, and then there are races like the Pineapple Cup,” said Spencer May, commodore of the Montego Bay Yacht Club and chair of the Pineapple Cup. “Its history, the demands of the course and the experience of finishing in Montego Bay make it truly special. We look forward to welcoming competitors back to Jamaica for another memorable edition.”
A Meaningful Return to Jamaica
The 2027 race carries particular significance for Jamaica and the Montego Bay Yacht Club following Hurricane Melissa, which struck the island in October 2025 as an exceptionally powerful Category 5 hurricane. The storm brought devastating winds, flooding and storm surge, severely affecting Montego Bay and communities throughout western Jamaica.
Against that backdrop, the return of the Pineapple Cup represents more than the resumption of a celebrated sporting tradition. It is an opportunity to welcome the international sailing community back to Jamaica, celebrate the resilience of its people and support the continued vitality of the local sailing community.
“Hurricane Melissa tested Jamaica in ways that none of us will forget,” May said. “Our thoughts remain with everyone who was affected, and we have enormous respect for the resilience and determination that have driven the recovery. Against that backdrop, we are especially excited to welcome the Pineapple Cup back to Montego Bay. Hosting this race is part of who we are as a club and as a sailing community. We are rebuilding, we are ready and we look forward to welcoming sailors from around the world back to Jamaica.”
A Classic Offshore Challenge
Over the decades, the Pineapple Cup has attracted accomplished sailors and competitive offshore teams from around the world, including legendary sailor Ted Turner, who won the race three times and famously called the Miami-to-Montego Bay course “the best ocean race in the world.”
For competitors, the appeal lies in the combination of a demanding ocean passage, changing conditions and the camaraderie that develops over hundreds of nautical miles at sea.
“The Pineapple Cup is not a coastal race that happens to be long,” May said. “It is an ocean passage with everything that comes with it. You leave Miami with the Gulf Stream ahead of you, settle into the rhythm of the Bahamas, navigate the approach to Cuba and then face the extraordinary run through the Windward Passage toward Jamaica. The conditions can change dramatically, and success requires a team to bring together navigation, sail handling, preparation, weather judgment and endurance. And when you finally make the finish in Montego Bay, you know you have accomplished something special. It is an experience every offshore sailor should have.”
The race’s partnership with US Sailing further strengthens its place on the offshore racing calendar and creates an opportunity to introduce more sailors to one of the sport’s most distinctive challenges.
US Sailing Names Pineapple Cup Its US Open Offshore
US Sailing CEO Charlie Enright brings personal experience to the partnership, having competed in the Pineapple Cup three times. His firsthand knowledge of the course and its demands underscores the significance of the race’s return.
“We’re thrilled to support the Pineapple Cup–Montego Bay Race as US Sailing’s US Open – Offshore,” Enright said. “I’ve raced this course three times, most recently in 2019, and I know firsthand what makes it such a special event. It’s a true offshore challenge that tests a team’s preparation, decision-making and ability to perform together over an extended passage. The course offers an incredible mix of conditions, strategy and competition, all leading to a finish in one of the Caribbean’s great sailing destinations. The Pineapple Cup has a remarkable legacy, and we’re excited to help carry that tradition forward, bring more sailors into offshore racing and make the 2027 edition a memorable one.”
The Montego Bay Yacht Club sees the partnership as an opportunity to honor the race’s heritage while building momentum for its future.
“The Pineapple Cup has a history that deserves to be respected, but great races cannot live only on their history,” May said. “They have to continue to attract great boats, great sailors and new generations of offshore racers. Our relationship with US Sailing and the designation as the US Open – Offshore help us do exactly that. We want the 2027 race to be both a celebration of what the Pineapple Cup has always been and a statement about where it is going.”
2027 Race Schedule
The 2027 edition will begin with the skippers’ meeting on April 9, followed by the race start in Miami on April 10. Competitors and their supporters will be welcomed to Montego Bay for post-race celebrations, including Jamaica Night on April 15 and the awards ceremony at the Montego Bay Yacht Club on April 18.
The Montego Bay Yacht Club invites offshore sailors, boat owners, navigators and crews to begin planning for the 36th edition of the race. With a legendary course, an important new partnership and a meaningful return to Jamaica, the 2027 Pineapple Cup promises to be a defining moment in the event’s history.
For further information:
Race information: Pineapple Cup–Montego Bay Race https://pineapplecup.com/
Registration: Yacht Scoring https://www.yachtscoring.com/emenu/16819