Generally speaking, the best time to sail in the Leeward Islands is between January and May. However, it is a year-round sailing destination.
If you’re looking for a more affordable time to sail, consider the shoulder seasons of November and June. The weather is still pleasant during these months, but there may be occasional rain showers and slightly stronger winds. Additionally, prices may be lower, and there may be fewer crowds.
The summer months, from July to October, are the least popular time to sail in the Leeward Islands, as this period coincides with hurricane season. While the chances of encountering a hurricane are relatively low, it’s still a risk to consider. However, if you’re looking for a quiet and affordable sailing vacation, this period may be worth considering.