Little Compass RoseCaribbean Compass   May 2015

Smooth Sailing in the Windward Passage

by Monica Pisani

Journey, our 42-foot sloop, Captain Jonathan and myself, his loyal first mate, started our sailing adventure on December 2013 leaving from Florida, although our home was New York City. We sailed the Bahamas, Haiti, the Dominican Republic and Puerto Rico, and we made our way as far south as Grenada. Since December 2014, we have been sailing north towards the Virgin Islands.
When we began to plan our route from Florida through the Bahamas and into the Caribbean, we realized there were two possible choices. The most popular was the Mona Passage, and the more unusual choice was the Windward Passage.

With the first choice, you leave the Bahamas via Turks & Caicos, to the northern coast of the Dominican Republic, and then down through and across the Mona Passage. The second choice was through the Windward Passage, leaving the Bahamas from Great Inagua, passing between Cuba and Haiti, then heading east towards the Eastern Caribbean. Our research included reading forums and magazine articles, and talking to anyone who had done either passage. One day, we found “A Cruising Guide to Haiti” by Frank Virgintino ( It was all we needed to solidify our route choice. We opted for the less traveled road, the Windward Passage.

We chose Clarence Town as our staging point. We needed a five-day weather window to make it to Great Inagua, the southernmost island of the Bahamian chain, then down through the Windward Passage, an almost 400-nautical-mile trip. The stop at Great Inagua had to be a quick one. The anchorage at Mathew Town is exposed to all but east winds, and the roll is tolerable only under light conditions.
The weather window opened up. Journey and another yacht, Fidelis, left Clarence Town bound for Great Inagua on an overnight sail. The wind was manageable but the seas were quite rough, with waves from every direction. Towards the end of the afternoon, the constant banging on the waves caused Journey’s boom vang to snap off the boom, crashing onto the deck and cracking the salon hatch. As if that wasn’t enough, our jib furler jammed, and would not unfurl. Great start!

Luckily, we were close enough to an anchorage called Windsor Point, where we dropped our anchors in the dark, to deal with the problems the following morning. Well, we woke up to a beautiful clear-water anchorage, and two fishermen trying to sell us the freshest lobsters. Our captains worked all day taking care of the boom vang and the jib furler, and as a reward, we all had the best lobster dinner ever!

We were underway early the next morning heading to Great Inagua. It was an uneventful overnight sail. We arrived early morning, we topped off fuel, water, provisioned, and checked out of the Bahamas, all in one long hot day. Then we spent a night in the rolliest anchorage ever. No surprise there!

We were up with the sun, and on our way south through the Windward Passage to Haiti. We raised our sails minutes after leaving the anchorage. We had light steady wind on our port bow, the sea was calm, and we were filled with anticipation.
As we got closer to the passage, Haiti and Cuba grew tall from the ocean floor. It was a welcome sight, after three months of beautiful but flat Bahamas. At dusk, we had Haiti on our port side and the sun setting behind Cuba on our starboard side. The ocean and the sky were painted with every shade of orange — unreal! I could almost hear Celia Cruz singing with her unequivocal raspy voice, and saying, “Azucar”!

As the night fell upon us, so did the moon lighting up our path. Bright night with calm seas, almost eerie, with hardly any waves or even ripples. The haze over the mountains and the smell of fires burning filled the air. That smell followed us throughout our time in Haiti. There is a very busy commercial shipping channel in the Windward Passage. Be aware.

We motored a bit, but sailed most of the way to the end of the passage, although we were expecting to lose some wind halfway south in the lee of Haiti. Our plan was to reach the southern tip of Haiti, and turn east at night, and take advantage of the lighter easterly winds, thanks to the katabatic effect. As we turned east, we had our last 50-plus nautical miles to go. We stayed only one mile offshore, to get as much protection from the trades as possible. We arrived at Ile-à-Vache, Haiti, by mid-morning.

Our nine-day stay in Haiti was one of the most incredible experiences we have ever had. It gave us an insight into human perseverance and resilience, and we learned that no matter what one can always find joy and hope.
Beautiful people, beautiful spot!

We’ll tell you more about that in next month’s Compass.


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