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Plotting a course to Caribbean sabbatical cruise

2020 May 28

John Kretschmer shares his wealth of knowledge on the logistics of a Caribbean sabbatical so you can do it too

And yes, you can still find secluded anchorages. Some nestle up to the edge of thundering reefs in the Grenadines or the windward side of Martinique and others lie off quaint villages set in the verdant valleys of St. Lucia and Dominica. I don’t deny that some harbors are overcrowded with yachts and the bareboat charter industry has expanded well beyond the Virgin Islands.  But the positive impact of chartering on the local economies has been substantial and is undeniably better and more sustainable than the cliched steel drum charade that accompanies the cruise ship hordes. It’s easy to pine for the good old days but most sailors, and certainly most islanders, are better off today than during those so called good old days. Sailors are responsible global citizens, and for the most part they’re travelers not tourists, with a keen interest in preserving the environment and local cultures.   

A glance at a chart of the Eastern Caribbean reveals that the islands stretch in a gentle arc bulging east but basically running north to south. The northern group, the Leeward Islands, reach from Anguilla to Dominica. The Windwards, continue south from Martinique to Grenada. It’s a compact cruising ground, less than 400 miles from top to bottom. And with fresh winds from the eastern quadrant 9 days out of 10, it’s good going in both directions. Tadji and I typically sail from St. Martin to Grenada and back several times a season. One of the advantages of the first route, via Bermuda, is that you can easily make your initial landfall in St. Martin, instead of the Virgin Islands. This eliminates the need to punch across the dreaded Anegada Passage, a notoriously rough 90-mile sail  from the BVI to St. Martin. If the trades, especially the accelerated winter trades known as the “Christmas Winds” are blowing, it’s not uncommon to encounter 10-foot seas and head winds of 30 knots or more in the Anegada Passage. Boats often linger in Virgin Gorda Sound, sometimes for weeks, waiting for a break in the trades and then dash to St. Martin under power. 

Captain’s hour often occurs during a row around the anchorage to chat up fellow cruisers.

There’s a better way. In January, we sailed from Tortola directly to St. Kitts. Our true course was 130° and it put the northeast trades just forward of the beam. We had a lively sail, with two reefs in the main, the staysail and a wee bit of headsail, knocking off 125 miles in less than 18 hours. From St. Kitts, we skipped down to its sister island Nevis. From there it was another close reach to Montserrat where we toured the once lush island now covered in ash. A few days later we rode the trades to Guadeloupe. We reached the eastern Caribbean with good sailing and zero underway engine hours.   

Most cruising is done in the lee of the islands, which is generally terrific sailing with fresh winds and small seas. However, some islands throw wind shadows that snuff out the prevailing trade winds. Generally speaking, the larger and higher the island, the greater the wind shadow. Guadeloupe casts the biggest, and Martinique, St. Lucia, Dominica and St. Vincent all throw wind shadows. In between flat calms be prepared for sudden downslope blasts that can go from 10 knots to 30 and back to 5, in seconds. With a bit of practice, you can see them coming. Sometimes it’s as easy as seeing the boat in front you suddenly heeling hard over. 

These wind shadows can reach far offshore. For this reason, it is sometimes preferable to sail to windward of the islands.  Sometimes you just want to feel the pitch of the Atlantic. Boats heading south from Antigua will often sail to windward of Guadeloupe to avoid the wind shadow on the lee shore and also to access lovely harbors and small islands southwest of Guadeloupe. Also, those heading north from the Grenadines sail to windward of St. Vincent, for a better passage to St. Lucia.  We often sail to windward of Grenada when leaving the Grenadines heading south. 

Another factor to consider is the wrap-around that happens when the easterly trade winds follow pressure gradients caused by land masses and follow the headlands, literally bending around them, resulting in headers and lifters. When sailing south from Antigua to the leeward side of Guadeloupe, the trades wrap the northwest tip of Guadeloupe, and the wind backs from east to northeast to north, allowing boats that have strayed west of the rhumbline a welcome lift for the approach to the lovely port of Deshaies.


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