When is the Sailing Season in the Caribbean?
The sailing season in the Caribbean starts mid November and lasts till the end of May. The high sailing season is from mid December to March, when the weather conditions are perfect for those running away from the harsh winters of Europe and North America. June and July are low because of the daily rain showers and the period from September to mid November is hurricane season. Although hurricanes are a rare occurrence in the southern Caribbean, they do prevail around Cuba. The only good thing about this time of year is that the prices are lower and you can get really good sailing yacht deals. However, not only do you run the risk of strong winds at that time of year, but you can also get stuck with no sailing winds at all.