St. Maarten Heineken Regatta
St. Maarten Heineken Regatta takes place Mar 4 - 7, 2027 in Simpson Bay, Sint Maarten. The dress code is Beach and party casual: swimwear by day, festival clothes for the concerts. Nothing on the island asks for more than that. Typical cost ranges from 300 to 3000 EUR per person.
Four days of racing around Sint Maarten in early March, spanning grand-prix boats, bareboat charters and multihulls, paired with one of the largest free music programmes in the Caribbean. The regatta village at Port de Plaisance books international headline acts each night, which pulls in a crowd well beyond the sailing fleet. The long-standing 'serious fun' tagline is accurate in both halves.
- When
- Mar 4 - 7, 2027
- Where
- Simpson Bay, Sint Maarten
- Dress code
- Beach and party casual: swimwear by day, festival clothes for the concerts. Nothing on the island asks for more than that.
- Cost
- Typical cost ranges from 300 to 3000 EUR per person.
- Weather
- 27 - 28C, warm and breezy with reliable trade winds
- When to book
- Book Sint Maarten flights and rooms 4 - 6 months out for March; bareboat charters for regatta week go by the previous autumn
- Getting there
- SXM (Princess Juliana), 10 min to Simpson Bay and the regatta village
- Where to stay
- Belmond La Samanna (grand, on Baie Longue on the French side), Sonesta Ocean Point Resort (adults-only, next to Maho and the airport), Holland House Beach Hotel, Philipsburg (boutique, on the Great Bay boardwalk)
- Official site
- https://heinekenregatta.com
How to attend
The Regatta Village concerts at Port de Plaisance are free and open to all, which makes this the most accessible major Caribbean regatta for non-sailors. Watch racing from Simpson Bay, Kim Sha beach and the coastal viewpoints. To compete, register a boat through the official site (entry runs via Yachtscoring), charter a bareboat locally, or find a crew berth through the event - the bareboat classes are specifically built for visiting amateur crews.
The Regatta Village concerts at Port de Plaisance are free and open to everyone, so no public ticket is sold - the official site only registers competing boats.
Insider tip
The regatta village concerts are free and book genuinely big names, so the island fills with non-sailors too. For racing, the Sunday finish into Simpson Bay is the best shore view and the Kim Sha beach bars put you right on the course.
Get inside St. Maarten Heineken Regatta
Booking matters here: book Sint Maarten flights and rooms 4 - 6 months out for March; bareboat charters for regatta week go by the previous autumn. Members track that window, what it really costs, and 573 more events across the season.
Free while in beta. One email when your invitation is ready, nothing else.