The Wailers to Headline 45th Annual St. Maarten Heineken Regatta
By St. Martin Sotheby’s International Realty · February 18, 2025 · Updated November 10, 2026
island-updates
This special performance comes as The Wailers celebrate the 30th anniversary of their iconic Natural Mystic album, which features some of Bob Marley & The Wailers’ most beloved tracks. Fans can expect to hear classics such as Natural Mystic, Positive Vibration, and Roots, Rock, Reggae, along with songs from their latest album, Evolution. Led by bassist Aston Barrett Jr., son of original bandleader Aston "Familyman" Barrett, the group continues to carry forward the legacy of one of reggae’s most influential bands.
"We couldn't think of a better way to celebrate 45 years of 'Serious Fun!' than with the legendary sounds of The Wailers," said Cary Byerley, Regatta Chair of the St. Maarten Heineken Regatta. "Their timeless music and positive energy perfectly capture the spirit of the Regatta, and we're thrilled to welcome them to St. Maarten for this milestone event."
The Wailers' performance will take place at the Port de Plaisance Regatta Village, where all four days of festivities will be free and open to the public. During the day, spectators can take in the thrilling yacht races from various vantage points around St. Maarten/Martin, before joining sailors and visitors in the evening for live entertainment and celebrations at the Regatta Village.
Each night, the Regatta Prize Giving will begin at 6 PM, followed by performances from a lineup of local and regional artists, including Tamillia, King James, Orange Grove, Trilla-G, and Alison Hinds. With The Wailers closing out the event on Sunday night, attendees can expect a grand finale that will have the entire island dancing beneath the Caribbean sky.
Beyond the shoreside festivities, the 45th St. Maarten Heineken Regatta is expected to deliver intense racing action, with more than 100 boats set to compete around the island between March 6th and 9th, 2025. Among the highlights are duels between 76-ft Maxi race boats, a fleet of over 20 Sunsail bareboats, and the high-performance Diam 24s, which continue to attract elite sailors.
With a mix of thrilling competition, legendary music, and island hospitality, the St. Maarten Heineken Regatta is once again shaping up to be a must-attend event.
Those interested in experiencing the celebration firsthand should be sure to contact our team of professionals today for assistance with planning, vacation rentals, and more.
Photo Credit: ConallviaWikipediaunderCC by 2.0 Attribution 2.0 Generic