
In the late 1970s, I spent a few months cruising the Windward and Leeward islands, gunkholing remote anchorages and living off the land, fish and fruit mostly. Sure, I was broke, but I was living like a king. Earlier in the year, I had raced across the South Atlantic from Cape Town to Uruguay, and we were making our way north to Florida. The yacht was up for sale, and the owner figured there would be a better chance of finding a willing buyer in the United States than in South Africa. He did not have the time to enjoy the boat and had left in Uruguay turning his lovely 55ft yacht over to me and a couple of other gypsies. We made good use of our time going native in the Caribbean.
Our first landfall was St. Lucia, and for someone who had never seen a tropical island I felt as if I had landed in a Disney movie, only better. Earlier in the day we had snagged a massive tuna and cut all 150lb of it into steaks, thick and red and delicious, with only one slight problem. We did not have any refrigeration, and the tuna wouldn’t stay fresh in the tropical heat. Our solution? We launched the dinghy and made the rounds to the other yachts in the anchorage, inviting them all to dinner on the beach. We then traded the carcass with some of the locals in exchange for their services making a large fire, the coals from which we used to roast the tuna. Other sailors bought salad, many bought rum, and my first Caribbean landfall turned into a party that lasted long into the evening.
Fast forward almost four decades, and my current self is land-bound, tied to a desk, raising kids in a house with a white picket fence. It’s a pretty good life, but far from the heady two decades, I spent bumming around the world on boats. I managed to circumnavigate a number of times and sailed to some of the remotest parts of the planet, but I never did return to the southern part of the Caribbean. I was growing older, sure, but I was still hankering for another adventure amidst the troubles of worrying how to meet the mortgage each month.

I have long maintained that I was born under a lucky star and I still believe it to be true. How else would you account for an out-of-the-blue call from an old friend that I had not spoken to for years. He was a yacht broker and had a boat that was listed but not selling. “No one is interested in going all the way to bloody Grenada to see a boat,” he told me over Skype. “I have convinced the owner to take the boat to St. Maarten. Any chance you could do the delivery?” I looked out my office window at the freshly fallen snow that had taken the spring daffodils by surprise and answered in the affirmative. I was Caribbean-bound and quite pleased with myself. A few days later I landed in Grenada to join a totally tricked out Privilege 465 catamaran, fully stocked and complete with crew.
When I landed I was greeted by a cab driver who went by “The Rock,” and we chatted amicably while the smell of frangipani wafted in through the open windows. I told him that I had last been in the Windward Islands 35 years earlier and that I liked Dominica the best. Back then we had taken a canoe up a river called the Indian River, and our guide had told me there were still cannibals living all the way up at its source. However, when I told The Rock about this he just laughed. “That was a story made up by the British,” he said. “They made it sound as if the natives were eating each other as a way to cover up how many were getting slaughtered by the British.” There are two sides to every coin I guess.
Waiting for me on board the boat was my crew—Kat from Slovakia and her boyfriend, Lenny, from the Czech Republic. They were terrific crew, both great shipmates, and excellent cooks. I made sure that the boat was stocked with rum, and the following morning we loosed our lines. I had turned back into the 21-year-old version of myself, full of wonder and ready for some island hopping. I hit the coordinates on the chart plotter, set a course for the Pitons and engaged the autopilot, quite liking these modern conveniences that had not been available to me the last time I cruised these waters.
The trades were blowing stiff and consistent, and we made good speed on a close reach. Aside from the 30-knot squall that came through after midnight, breaking the outhaul and causing some general commotion, it was a fast sail. By 0300 we had made it to the Pitons, but instead of stopping in for a trip down memory lane, I looked at the murky outlines of two mountains that mark each end of a sandy bay and decided to keep going. Secretly I was glad. My memory of the Pitons is a party that went long into the night on a deserted sandy beach. The reality, thanks to Google Earth, is that there is now a swanky resort there with rooms starting at $1,200 a night. Not my idea of a good time, so we altered course slightly and headed for Martinique.
By the time a damp morning rolled around we had made landfall on the southern end of Martinique and saw the lush, verdant landscape dotted with small settlements. Shortly thereafter we sailed past Fort-de-France, the largest town on the island. I was looking for something a little less busy and decided upon Saint-Pierre, a tiny settlement toward the north of the island. We anchored in a shallow bay just off the main commercial dock, and I felt transported back in time.

Towering over Saint-Pierre is Mont Pelée, a semi-active volcano that destroyed the town in just 10 minutes at the beginning of the last century. Saint-Pierre used to be the capital of Martinique and was so cosmopolitan that it was dubbed the “Little Paris of the West Indies.” Let me assure you, though, that the town these days bears no resemblance to Paris. In the spring on 1902 Mont Pelée started to emit sulfurous gasses, but the local authorities quieted the townspeople by telling them it was just normal activity. The governor even made a trip to the town to show how safe things were. To make his point he brought along his wife. Unfortunately, the following morning the volcano erupted and super-heated gas and burning ash rained down on the town with a force estimated to be 40 times stronger than the nuclear explosion over Hiroshima. The governor and his wife both perished, as did nearly all of Saint-Pierre’s 30,000 inhabitants. In fact, there were just three survivors, one of them a prisoner who was locked in the solitary confinement cell deep in the bowels of the jail. He escaped with only minor burns. The new governor commuted his sentence, and he spent the rest of his days as a side-show act for the P.T. Barnum circus.
Walking around Saint-Pierre you can still see much of the burned out foundations. They have been incorporated into new buildings blending old and new in a strange mix of triumph over tragedy. There is not much to the town. The most popular place was a sailor’s bar on the main street, and by the looks of things, the second most popular place was a shop that sold coffins on a side street a block back from the harbor. I drank a couple of beers in the bar, enjoying the numerous languages being spoken, and made my way back to the boat just in time to see if I could spot a green flash as the sun slipped, sizzling back into the ocean. Alas, no flash.
The next day the wind was light, so we got an early start and motored close inshore, marveling at the towering green mountains that dropped straight into turquoise water. Once clear of their lee the trades kicked up a steady easterly breeze and with full sails set we dialed in a course for Dominica. Prior to leaving, I had discussed with the owner of the boat my desire to stop off there, but that suggestion was met with a long silence. At first, I thought the Skype connection had dropped, but it had not. “How familiar are you with guns?” he asked. “I have heard numerous stories of criminal activity in Dominica.” I am very familiar with guns, having spent two years in the South African military, but don’t ever again want to feel the weight of a gun in my hand. “Don’t worry,” I replied, “I’m not stopping.” And we didn’t. Instead, we spent what was quite likely the most enjoyable day of sailing that I have experienced in 40 years—steady wind, a luscious landscape to leeward and a lively yacht, which is about as good as it gets.
We pressed on, and it was postcard-perfect sailing. We toyed with the idea of stopping for fuel in St. Kitts but ruled it out when the friendly voice on the VHF informed me that we would have to clear customs and immigration and then take a taxi into town to get diesel. It seems that the multimillion dollar, brand-new marina was not able to dispense a gallon of gas. So, instead I set a course for St. Barts—or so I thought until we got close enough to see a mass of masts and I remembered that there was a regatta going on. No way was I going to deal with that mess. So we dropped the hook in a very picturesque cove on the island of Île Fourche, which is between St. Barts and St. Maarten. Steep cliffs on either side or our anchorage protected us from the breeze and a sandy bottom provided good holding. As night fell I could see St. Barts lit up like a candle and was very happy I was not there. The gentle slap of waves against the hull provided a perfect soundtrack for a night at anchor.
Reluctantly, the next morning it was time to re-enter the real world. I had snagged a fish the day before, a cero, and leftover fish and salad and a glass of cold white wine took some of the pain off shedding my former self and pulling on my grown-up 58-year-old pants. It’s quite remarkable how a few days in the islands can take years off your life, literately and figuratively. Our few days at sea had indeed instilled some of that sense of wonder that had seemingly become lost with the passage of time and the traffic and jams of life. The islands of the West Indies are just the same as they were when the early explorers first set eyes on them. The towering mountains thick with vegetation, the turquoise waters teeming with tropical fish and the people caught in a time warp. Sure there are more people, but it’s a paradise that has to be seen to be enjoyed.

One or Two?
Most of my sailing experience has been on monohulls. However, my more recent passages have been on multihulls, and I have to say that I have enjoyed the multihull voyages more. There are a couple of reasons for this, the most obvious being that multihulls do not heel. This is a big benefit when on a longer passage because it’s tiring sailing a boat that is always heeling and pitching. In the past, I would take it for granted that on any offshore passage there would be plenty of time sailing with the wind up and rail down. But now that I have sailed many thousands of miles on multihulls I realize how less taxing it is.
Similarly stowing our belongings below is much easier on a multihull. In my days on a monohull we would make sure that everything was stowed securely; otherwise, there would be things flying around the cabin. Not so with a multihull. Even with the breeze up, we could leave a glass of water on the nav station and not have to worry about it soaking the laptop.
I have also found multihull sailing to be considerably drier than my days on a monohull. Sure, there are waves that break off the bows, but the boats are wide, and the bow waves rarely get back to the cockpit: in stark contrast a monohull where your chances of taking a wave in the face are pretty high. There is also more air belowdecks on a multihull. With the rail down and breeze up you don’t need to batten the hatches like you do on a monohull. It’s mostly just fine to keep the windows and hatches open, and let the cool night air blow through.
The only point of sail that I prefer a monohull over a multihull is downwind with a spinnaker up. There are very few things more fun than picking your wave and then surfing down. Multihulls are, for the most part, unwieldy, and you do not get the same sensation when sailing off the wind.

Squalls, Sails and Sea-Breeze
This passage was a pretty straightforward one. During the time of the year that we made the passage the prevailing winds were mostly out of the east, and as we were heading north I was not concerned with having to deal with any upwind work (which can make a Caribbean passage a touch more difficult). What we did have to deal with, though, were squalls. Luckily, our radar was able to pick them up, and I could track the direction they were moving and try and avoid getting hit. However, more often than we would still get a good drenching, though it was not the rain that was a problem, but the sudden increase in wind. Fortunately, after the first squall, I was able to prepare for that amount of wind. The mainsail had a stack-pack setup, so dropping in two reefs was fairly straightforward: providing we got the sail down before the wind got up. The genoa was on a furler and rather than deal with a reefed headsail we got rid of it altogether and rode the squalls out under reefed mainsail alone.
During a squall, the radar remains your best friend because you can see quite clearly which direction the squall is moving, and we would try and find the best point of sail to the nearest exit point and get out of it as quickly as possible. I can remember sailing in the Caribbean many years ago before radar and often getting stuck in squalls for a long time. This was probably because we were going in the same direction as the squall but did not know it.
You also need to remember that islands create their own weather, especially mountainous ones like Dominica. Wind shadows and downdrafts create their own special kinds of problems, especially if you are close inshore. We purposely put some distance between ourselves and the islands with higher elevations, especially at night. In doing so we were able to remain in more consistent breeze both in terms of strength and direction.
See the slide show A Pirate’s Life for Me here
Brian Hancock is an accomplished offshore sailor having competed in three Whitbread Round the World races. He has written a number of books including two memoirs and a tome on the subject of sails and sailmaking. He is the owner of Great Circle Sails and contributes regularly to SAIL Magazine
MHS Fall 2016