Well not exactly... just Montserrat, Nevis, Martiniques et Les Saintes. And even not.... I only went ashore into Martinique and Les Saintes, a small group of islands part of Guadeloupe.

I left Puerto Rico with some North wind, turning NE later on, and a forecast for no wind within a few days and for a few days. So I decided to sail direct to Martinique, my southernmost goal for the year. There, from Ti Punch to fresh baguette, from baguette to camembert, and camembert to a large array of French pleasures, time did fly, untill almost Easter. I made commitments to spend Easter in Luperon, so a quick return trip was on order. A few days in Les Saintes, a night sail by Montserrat - volcano gave a show that night! - a stop of Nevis for some sleep, than an overnight passage south of St Croix and landing in Ponce, Puerto Rico.

Following is just my experience sailling the Caribbeans. As they lay on an N/S oriented, with the tradeswind blowing from the east, they are famous for allowing sailling from one to the other and back almost anytime.
Great or what?!?
Well, my experiance is a bit different. quiet a few islands are large and tall, so they totally block the wind on their leeshore. Getting some back would means going some 15 to 20 miles offshore, but then offcourse, coming back to the destination point would be dead upwind, and then, getting closer, in no wind. Or one could decide to pass the islands on the Atlantic side, where there is plenty of wind. Yes indeed, but it require to go upwind between the islands first. These passes act as venturi pipes, so the wind there can get rather strong. In addition, the long Atlantic swell as nowhere to go but between the islands, where it becomes kind of chaotic, short, and as the wind is accelerating, well, it become intimidating. So going to the windward side is a handfull under sail - or even motoring (however, the way back is a lot of fun).
Finally, on the caribbean sea side, at the edge of the islands exist some turbulent zones, where the wind really does wahtever. In fact, most of the boats I met were under motor or motorsailing. Professional skippers in Martinique confirmed to me that yes, passing Martinique, Guadeloupe or Dominica strictly under sail is an exercise requiring a lot of patience.

So, going down there, I kept sailling until about 4 miles from Anse Mitan, inside the bay of Fort de France. Passing Guadeloupe took 20 hours, Dominca another 9. On the way back, I sailed from Martinique to Les Saintes passing on the windward side of Dominica. Sailing there was great, however passing between Martinique and Dominica was not called pleasure sailing. From Les Saintes, I motored to pass Guadeloupe, then sailed windward of Montserrat, leeward of Nevis and whatever after that, across the Saba banks, South of St Croix and landed in Ponce, PR.

Now this is only my experience, and over a short span of time. I do not say that it is this way, and some skippers will likely disagree with me. How however, I believe that if you go sailing in the Caribbeans.... you should not forget to top off that diesel tank !

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