Sailing in the Eastern Caribbean is fun, especially when you can “pick” your weather windows to go where you want. That is easier to do with your own catamaran with less of a time frame than when you charter a catamaran for a week or two week holiday. Nevertheless, the islands in the Eastern Caribbean lay relatively close to each other, maximum a day sail away, offering a multitude of great destinations and options. The size of the catamaran, the skill of the sailors, flexibility, schedule and the weather will decide how fast you go and where you end up.
There are a few things to note when you plan a sailing trip in the Eastern Caribbean. One of them is “the sailing season”. From November until June, it is high season in the Caribbean, on shore and on the water. Many tourists escape the winter in their own country, prices go up, beaches can get crowded and harbors fill with (charter) boats. It is busier everywhere, but the climate is wonderful and the sea refreshing. The trade winds mostly come out of the northeast and are stronger than in the summer (15-20 knots). This can make a longer crossing less comfortable. The seas are consequently bigger and will come out of the north frequently due to cold fronts originating in Canada and the States. The biggest disadvantage of this phenomenon is that a lot of beautiful harbors become very uncomfortable with a swell rolling in from that, unprotected, direction.
The other season is “hurricane season” from June until November, with August and September known to have the most potential. The winds are lighter (10-15 knots), typically out of the southeast with no north swell running anymore. Harbors and shores are less crowded, the most magnificent beaches almost deserted. It is hot, however, and the warm ocean doesn’t always provide the desired coolness. The biggest threat, of course, is the possibility of a hurricane. Many of the Eastern Caribbean islands have “hurricane holes”, where you can tuck your catamaran into the mangroves, attach a bunch of lines and deploy all your anchors. The best solution is to spend your summer months cruising within a day sail of safer environments like Grenada, Trinidad, Venezuela or Luperon in the Dominican Republic. Or, totally get out of the hurricane belt.