This question comes up a lot, and honestly there’s no single perfect answer. Winter has amazing weather and steady winds, but yes, it’s busier and prices are higher. Shoulder months can be quieter and cheaper, and storms are not as constant as people fear. When I planned my trip, browsing https://12knots.com/en/yacht-charter/destinations/caribbean/st-martin/ helped me compare seasons realistically, not just marketing talk. The key is flexibility: if you’re okay adjusting dates slightly, you can find great conditions without crowds. Locals sail year-round, so it’s more about your comfort level than strict rules.