To approach the eastern Caribbean from the west, directly into the trade winds, is never going to be easy. This is why the passage from America through the Bahamas has gained the name The Thorny Path. As British gentry used to say “a gentleman never sails to windward.” However, with careful planning the troublesome trades and large landmasses can be used to your advantage. There are two basic choices to head east from America: the off-shore route or the coastal route.
The off-shore route is best traveled in November, when the risk of hurricanes is low and the northerlies that bring heavy seas and stronger winds have not yet kicked in. It is best to get as much easting as you can north of twenty-five degrees north and to not turn south until you have passed sixty-five degrees west. Winds are predominately from the northeast during this time but become stronger and from a more easterly direction after January. So the window of opportunity is small.
Bermuda can be a good place to stop if you wish to break up the journey. Crossing the Gulf Stream should always be made at right angles, then, once cleared, a course laid for Bermuda. The best time to make this passage is between seasons. Although summer is the better option, this coincides with the start of hurricane season and many boats choose to travel in late November, so they can join the start of the Caribbean sailing season. When leaving Bermuda in November the winds can be fickle and light as the area lies within a belt of variables. It’s a good idea to motor if necessary to get as far to the east as possible and only turn south when you have reached the longitude of your destination. This helps avoid the strong northwest current that runs parallel to the Bahamas.
Many cruisers choose the coastal route, enjoying the countries that they travel through at a much slower rate. They take advantage of the fronts that sweep down off the coast of North America. This is the route that we took. We knew this was going to be the toughest part of our journey as we inched our way into the teeth of the trade winds. We crossed the Gulf Stream to the Bahamas in January and stayed until April, with easy day sails down the islands to Georgetown and finally Mayaguana, using the clocking winds as the cold fronts approach and then seeking a safe anchorage as they passed.
The Gentleman’s Guide to Passages South by Bruce Van Sant covers this route in detail, explaining how to use the fronts to move east and south as well as how to use the night lees over the large landmasses like the Dominican Republic and Puerto Rico.
In the winter months from January to March the fronts or ‘northers’ can be used to sail south and east. The later in the season the slower and less frequent they become. We made it to Mayaguana and then over to the Turks and Caicos by the beginning of April.  As Van Sant’s book explains, the large landmass of Hispaniola creates a night lee sometimes extending up to 30 miles offshore. This combined with 15kts of wind from the east makes a good time to cross from Big Sand Cay. You should also allow for about half-a-knot of current setting west-northwest. We were unable to make it all the way to Big Sand Cay, as the motor across the reef-strewn banks was too far to make in daylight with our little engine and heavy boat; instead we chose to depart from French Cay further to the west. We were unable to make our course to Luperon in the Dominican Republic,  so fell off the wind and then beat back over the eight miles we lost the following day.
The advice offered by Van Sant time and time again is always to wait for the right weather. The forecast must be constantly monitored so that you are ready to take advantage of any favorable weather. We had a months wait in Luperon for the right weather to continue east. The trick is to wait for the easterlies or south-easterlies to blow 15kts or less to take advantage of the nocturnal wind. You inch your way along the coast at night and tuck into harbor when the wind picks up during the day. Currents can run up to 2kts or more around the headlands and can make for slow progress. For some it is possible to travel all the way across the Mona Passage with the right weather. But our weather window didn’t allow for this and so we pulled into Samana on the east coast of the DR after a day and two nights of motor-sailing. Again strong easterlies prevailed and we had another month’s wait to cross the notorious Mona Passage.
There are different approaches to crossing the Mona Passage. For those wishing to sail, a force 3-4 northeasterly using the nighttime lee of both the Dominican Republic and Puerto Rico will have you across in about 30 hours. Contrary currents are to be expected.  The Hourglass Shoals are to be avoided as the Puerto Rican Trench is one of the deepest in the world and seas can pile up in this area. We had settled conditions for our trip across and made good time.
Once in Puerto Rico you can navigate the south coast; getting up early at daybreak or before and traveling ten or 15 miles or so until the trade winds kick in. This is a great way to see the island. Before you know it you will be in the Virgin Islands and ready to turn south to the Leewards and Windwards.
Rosie and her husband Sim Hoggarth, both from the UK, have cruised the Caribbean and North America for the last seven years aboard Alianna their Corbin39.
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