Sailing is a big business in the Caribbean region, despite it may lack the fiercely competitive nature of some of the other sports. Sailing is popular here due to the fact that the islands are surrounded by some of the most scenic waters in the world, so it would be such a waste if you don’t try sailing during your Caribbean break.
Besides, yacht racing takes place across the islands all year round, with the participation of the best sailing teams in the world. So, remember to check out racing calendar for upcoming races in the region you’re traveling to. You might lucky to witness one.
If you in for a treat, you can easily rent boats from your all-inclusive resorts, ask the staff for some direction and you are ready to adventure.

But when are the best times for sailing, you may ask?
The best time to sail in the Eastern Caribbean islands such as from St. Thomas to Grenada is from March through June, although the weather in Caribbean is nice year round. There are fewer tourists, and the weather is stunningly with less clouds, settled weather patterns, tropical fruit and flowers are blooming.
Early summer is when the trade winds calm down, so yachts can visit anchorages and islands such as the islands of Saba and Statia in the Leeward Islands that are difficult to get to during stormy, windy weather.
Besides Saba and Statia, there are other options for anchorages in early summer such as the whole Eastern side of Martinique with a lagoon on the windward side ideal for cruising, between the outer reef and the mainland.

Weather No Longer Effects Rates

Many resort don’t often offer specials rates in the summer as yachts in the Virgin Islands are so well booked – they easily get 25-35 weeks of charter a year. Hence, if you are interested in sailing, you should check and book in advance as they would not discount for the entire summer months.