Experience the Ultimate Caribbean Holiday at the St. Maarten Heineken Regatta
Bird's-eye view over Simpson Bay, where all the Regatta action happens! © Volano Media
February 4, 2026 - Simpson Bay - The St. Maarten Heineken Regatta is a complete Caribbean holiday experience, offering something unforgettable for sailors, spectators, families, music-lovers and adventure-seekers alike. From world-class racing to beachside viewing and vibrant nightlife, the Regatta blends sport, culture, and celebration into one iconic destination event, taking place March 5-8, 2026.
Bring Your Own Boat: Race, Cruise, Stay a While
For sailors arriving under their own sails, St. Maarten is the perfect seasonal base. International race teams stay on the island for an average of 20 days, allowing plenty of time to race, cruise, and explore. With so much to see on both Dutch and French sides of the island, sailors enjoy protected anchorages, full-service marinas, and some of the best yacht services in the Caribbean. Many crews choose to stay for weeks, or even the entire winter season, using the Regatta as the anchor point of their Caribbean adventure.
Villas with a View: Watch the Regatta from Your Balcony
The St. Maarten Heineken Regatta is proud to partner with Covecasa, an international luxury property marketing and management company with some of the island’s top villas entrusted to their worldwide proven systems and processes. This year, the event has selected two “Villas with a View” from their curated selection of ocean view villas that provide the best views of the St. Maarten Heineken Regatta race course area. Perfect for crew houses or families of sailors to enjoy regatta viewing from the comfort of your own villa. Check out these exclusive properties on www.booking.heinekenregatta.com
“For St. Maarten property owners, the Regatta serves as a reminder of the island’s incredible potential. Covecasa’s partnership with the event highlights our unique approach to hospitality—focusing on the digital and physical optimization of Vacation Rental villas.” said Ian Lobas, Fractional CEO of Covecasa Caribbean. Owners interested in having their property featured in future events or maximizing their current rental yield are encouraged to connect with the Covecasa team during Regatta week to get a free property audit and learn more about their bespoke asset marketing & management services that have set a new standard for SXM.
Capture epic views of the Regatta from one of our selected "Villas with a View." This stunning view is from the balcony of Covecasa's Pelican Paradise villa, available for the St. Maarten Heineken Regatta © Covecasa
The best beachside spectating of the Regatta will be at Grand Case for the Diam 24 Race day on Saturday, March 7, 2026 © Digital Island
Weekend Getaway: Front-Row Spectator Action
The Regatta’s weekend program is designed for unforgettable spectating. Friday’s iconic Around the Island Race turns the entire coastline into a viewing platform, where you can yacht-spot from beach bars and seaside restaurants around the island. Saturday sees the return of the Grand Case Beach Stadium Race, where high-speed Diam 24s race right in front of Grand Case’s world-renowned beach clubs. On Sunday, head to Mullet Bay, where the entire fleet rounds a mark inside the bay, delivering spectacular close-up racing for beachgoers.
Voluntourism: Give Back While You Get Involved
Visitors can also combine their holiday with purpose by joining the Regatta’s international volunteer team. Whether for one day or all four, volunteers of all ages support race committee operations, onshore logistics, media, and more. It’s a unique way to go behind the scenes of the Caribbean’s biggest regatta and music festival, and become part of the Regatta family. Sign up to volunteer online: https://www.heinekenregatta.com/volunteers/
Regatta Village: Free, Festive, and Open to All
Each night, the Regatta Village comes alive and is open to the public – for free! Enjoy daily prize givings followed by live music, an international food court, and an electric atmosphere. The celebrations culminate on Sunday, March 8, with Inner Circle “The Bad Boys of Reggae” as the headline performance. Check out the full schedule here: https://heinekenregatta.com/schedule/
Make It a Holiday to Remember
Looking for the perfect holiday gift or experience upgrade? Book official spectator boats, reserve a villa with a race-course view, or secure VIP tickets for your crew for headliners Jeon (Saturday) and Inner Circle (Sunday) via booking.heinekenregatta.com. Catch the Regatta vibes by picking up some official swag at Shipwreck Shops and Budget Marine, in stores now!
Whether you sail, spectate, volunteer, party or simply soak it all in, the St. Maarten Heineken Regatta delivers a holiday unlike any other: where world-class racing meets Caribbean celebration!
The St. Maarten Heineken Regatta is known for it's world-class racing and entertainment. All 4 days of the regatta conclude with a night full of free entertainment and festivities at the Regatta Village, featuring live bands, an international food court, and marina-side vibes
Watch the 2025 St. Maarten Heineken Regatta Wrap Up film to get a feel for the "Serious Fun!" © Volano Media
######
