Racing
Our fleet's racing calendar includes six Diam 24 Caribbean Championship Regattas and several other multi-class events. Some are short, high-tempo, Grand Prix style; others are long-distance races with offshore passages between Saint Martin and neighboring islands like St Barth and Anguilla, testing endurance as much as boat speed. And a few are marquee, world-class events, but none bigger than the Heineken Regatta, one of the Caribbean's best-known sailing regatta with plenty of action on the water and an extensive entertainment lineup on shore.
Whether you're training for your first Grand Prix or building toward a full championship season, the calendar below lays out what's coming up — where, when, and how to find out more.
Caribbean Championship Regattas
| Event | Start | End | |
|---|---|---|---|
| Grande Case Grand Prix | Sat, Nov 14, 2026 | Sun, Nov 15, 2026 | Details |
| Course D'Alliance | Fri, Dec 4, 2026 | Sun, Dec 6, 2026 | Details |
| Caribbean Multihull Challenge | Thu, Feb 4, 2027 | Sun, Feb 7, 2027 | Details |
| Heineken Regatta | Thu, Mar 4, 2027 | Sun, Mar 7, 2027 | Details |
| Friars Bay Grand Prix | Sat, Apr 17, 2027 | Sun, Apr 18, 2027 | Details |
| Anguilla Grand Prix | Fri, May 14, 2027 | Sun, May 16, 2027 | Details |
Regattas
| Event | Start | End | Website |
|---|---|---|---|
| Keelboat Race Oyster Bay Weekend | Sat, Oct 31, 2026 | Sun, Nov 1, 2026 | Details |
| Keel Boat Series Day 1 | Sun, Jan 10, 2027 | Sun, Jan 10, 2027 | Details |
| Heineken Warm Up | Sun, Feb 28, 2027 | Sun, Feb 28, 2027 | – |
| St Barth Mini Bucket | Thu, Apr 1, 2027 | Sun, Apr 4, 2027 | – |
| Keel Boat Series Day 3 | Sun, Jun 6, 2027 | Sun, Jun 6, 2027 | Details |
Club Racing
Outside the championship calendar, SMSC runs a regular club racing schedule for members and visiting crews. These are shorter, lower-stakes events — still competitive one-design racing, and a good way to log time on the boats between bigger events. New to racing? Club races are also the easiest way to get a feel for one-design fleet racing before committing to a full regatta campaign.
Ready to Race?
Racing with SMSC starts with picking your path. Charter a boat for a single regatta, join a Training Clinic and Race Prep session ahead of your target event, or race with us for a full season of club racing. Get in touch with your dates and goals, and we'll help you build a race schedule that fits.