Fifty Shades of Blue—A landlubber’s initiation to sailing the Caribbean

images-1For years my husband had been nostalgically recounting his youthful experiences of sailing the Caribbean. After retiring two years ago, he spoke increasingly of rediscovering those happy times. For my part, I dreaded the fearful day when I might have to move aboard a sailboat for a longish period.

Let me be clear about the source of my fears. It wasn’t seasickness; I had sailed before—a few days on the Cote d’Azur and the Greek islands—and hadn’t suffered any queasiness at all. My dread of this new extended venture came rather from a kind of claustrophobia, the fear of being trapped for weeks on a small craft in a large expanse of water. I was apprehensive about giving up my daily exercise routine and my customary trips to the shops and other social outings. I worried, too, about being cut off from my virtual community. Would I be able to surf the internet, stay in touch with family and friends at home in Europe, and receive my eagerly awaited magazine subscriptions electronically? But mostly I worried about whether or not, in sharing the confines of a sailboat with others, I could preserve my private space: that precious time which I needed each day to be alone with thoughts, to read and reflect.

In July 2012, while visiting St. Lucia, we met Ian and Leslie Gallacher, a truly charming couple from South Africa, who had already put my husband’s dreams into practice. Having sailed their 48-foot catamaran, Jangles, from South Africa, they were cruising the Caribbean with their three children. A friendly and generous offer was made over cocktails; we could join them on Jangles and sail with them when the children returned to school. I almost hoped it was the cocktails talking and the idea would dissipate with our hangovers the next day. But in late 2012, the offer was renewed and a plan took shape; we would board Jangles in January of the new year and sailwith Ian—Leslie had returned home temporarily with the children—from the British Virgin Islands, all the way to Trinidad. In short, our trip would span the whole of the lesser Antilles and cover a distance of over 600 nautical miles, a rather daunting prospect for a landlubber.

Despite my misgivings, in January 2013 my husband and I were prepared to clamber aboard Jangles at Leverick Bay in Virgin Gorda, one of the small islands that make up the BVI. In planning our trip, we had tried to keep luggage to a minimum in the expectation that our quarters would be cramped and space below decks at a premium. But as we waited on the dock for Ian to bring his craft alongside, our big, boxy, wheeled suitcases seemed to form a disturbingly large pile. After passing our bags over the ship’s rail and onto the deck, we stepped aboard. Going below to our cabin, our misgivings dissipated. It was surprisingly, even delightfully, roomy. Every nook and cranny had been artfully fitted to provide storage. I had more shelves than I knew what to do with, and our personal effects disappeared effortlessly into our allotted space. While I unpacked our bags, the men busied themselves with preparations to leave Leverick Bay.

Ian is the most considerate of men and, knowing about my fears, had decided to ease me gently into the sailing life. So our first “passage” was very short indeed; 20 minutes under motor to the shallow waters off nearby Bitter End Resort. Here we were to spend two nights. Bitter End was more sheltered from the easterly winds than Leverick, so my first night onboard would be as calm as possible. And I was delighted to learn that I would not have to abandon terrestrial pleasures straight away. We took a short dinghy ride to shore and hiked for several hours around the hills adjoining the resort. Returning to Jangles, we cooled down with a plunge into the azure waters off the back of the boat and then relaxed with cold drinks on the “trampolines” on Jangles’ front deck.

The next morning I could even put in some workout hours at the gym at Biras Creek Resort after Ian kindly ferried me ashore. But, later in the day, as we indulged in another two-hour hike, I realized that these vigorous walks in spectacular natural settings could replace the drudgery of the gym treadmill, while swimming daily would substitute nicely for those hours on the weight bench.And sailing, in the Caribbean at least, did not mean confinement. As I would soon realize, most sailors, in fact, spend much more time ashore than on board.Such is the beauty of the islands and the variety of sites to visit.

That evening, after the traditional swim and evening drink back on Jangles, Ian dazzled us by preparing a South African dish called boboti. Jangles’ kitchen, handsomely equipped with the latest modern appliances and conveniences, and with vast cold storage and freezer space, hid endless possibilities of culinary delights. Another prejudice laid to rest. Previously, the thought of eating on a sailboat had conjured up images gleaned from old pirate movies of dinners of hard, weevil-infested biscuits and salted meat of dubious origin and quality. And wasn’t the food at least partially responsible for that famous mutiny on H.M.S. Bounty? But I was learning that, just as Ian was no Captain Bligh, life on a sailboat held no terrors in the gastronomy department. To the contrary, the combination of fresh seafood and produce from well-stocked stores in most of our ports of call would allow for first rate onboard dining, not to mention the many excellent restaurants along the way.

The following morning, the sky and sea seemed to compete for the title of the most spectacular shade of blue, and, after a mere 48 hours, I was already falling in love with the boating life. The two-hour downwind sail to Soper’s Hole, Tortola, was perfectly lovely; I spent it sunbathing on the trampolines on the foredeck. The motion of the boat, pushed by a mild breeze and gentle swells, was almost serene. With no feeling of queasiness, I was starting to think I was a natural sailor. My feeling of satisfaction grew even stronger at Pusser’s Bar in the Soper’s Hole marina, owing both to the local concoction dubbed “Painkiller”—dark rum, coconut cream, juice—and the friendly chats we had with other slightly intoxicated “boaties.”We soaked up the happy hour’s cocktails with jalapeno poppers—deep-fried delectable peppers stuffed with cheese—and a grilled shrimp caesar salad and slept like logs that night.

Having dealt with provisioning at the well-stocked marina store, our destination the next morning was Great Harbour on Jost Van Dyke, another island in the BVI chain justa short sail from Tortola. We wanted a relaxing time before our first longish passage to St. Martin,106 nautical miles nonstop. I was getting terribly smug about it all, and so I didn’t really worry. We passed the evening at Foxy’s Bar and Restaurant, a local institution, where you sit under torn and faded flags, photos, and an assortment of T-shirts and underwear donated and autographed by inebriated patrons hailing from many countries of the world and waving in the gentle breeze. If your timing is right, you will meet Foxy himself, the aged but brilliantly lucid founder of the establishment, who will regale you with a monologue in rhyming verse about any place you mention as your homeland. By way of food we passed on the rather overpriced lobster and opted for a delicious local tuna with curry sauce, which was followed by heavenly key lime pie.














The next morning we scrambled up to the surprisingly steep summit of the little island, a hike that offered spectacular views but left us with seriously sore muscles. We had the whole afternoon to recover, however, and we spent iton the dazzling sands of the aptly-named White bay and paddling in its aquamarine waters. Having taken in a spectacular sunset, we set off on our night sail to St. Martin. I naively wondered what was on the menu for dinner and thought of asking Ian as soon as the boat reached open water. But then my nightmare began. Everything was rattling and rolling, hissing and shaking, and I was convinced my last hour was at hand. It was a moonless night and dark as pitch; our little craft seemed to be sailing into oblivion, and none too smoothly at that.Ian later explained the BVI to St. Martin passage is notoriously difficult, due to the prevailing winds and swells, and that the sailing conditions on that night had been particularly rough, so I shouldn’t be discouraged if I had spent the night and the rest of our 21-hour journey with a green face and chattering teeth buried in a plastic bag.

Arriving finally at St. Martin’s, still shaky from my ordeal, I was surprised to see a flotilla of yachts, ranging in size from the smallest daysailersto Roman Abramovich’s giant Eclipse, anchored at the entrance to Simpson Bay. The harbor inside can only be accessed when the swing bridge is lifted up at scheduled times. It is a magical “open-sesame” moment: the traffic on land stands still for ten minutes or so and onlookers gather to gawk at the hundreds of millions of dollars’ worth of super-yachts and sailboats as they file in to the bay, like so many models on a fashion show catwalk. We waited our turn then slipped through the narrow opening between the bridge pylons and docked at the marina.









Marina life has its own pleasures and conveniences. No need to lower the dinghy to go anywhere, just step onto the dock and walk to restaurants, beauty parlors, and shops, all of which St. Martin’s has in abundance. But, surprisingly for someone favoring urban comforts, I couldn’t wait to get out of the marina and back to open water. I found the shoulder-to-shoulder press of other boats at the dock annoying and the walk to the communal bathroom and shower facilities tedious. Also, the murky waters of the marina were a stark and unattractive contrast to the crystalline shades of blue I so much enjoyed. Amazingly, I had already come to love the freedom and relative solitude of anchoring in a calm little bay where I could jump into the sparkling blue water whenever the feeling struck me.And I was beginning to appreciate what I heard so many sailors speak of in loving tones—the self-sufficiency oflife on a boat. Rather than living “rough,” inhabitants of a modern cruising sailboat enjoy all the comforts of home in a marvelously compact and efficient environment.

We spent five days in St. Martin, as Jangles needed some maintenance work. It all looked like a great bore to me, and I almost felt sorry for Ian when I realized he actually enjoyed the “tinkering” part of sailing. We toured the whole island, taking advantage of duty-free shopping in Philipsburg on the Dutch side where many of the French inhabitants also choose to shop, work, or live. While in St. Martin, we feasted on ribs and our favorite jalapeno poppers at Jimbo’s in the marina, and we delighted in sophisticated sushi and sipped lichi martinis at Bamboo Bernies.

Our next stop was the ruggedly beautiful island of Saba. Unlike many other islands in the Antilles chain, with their gently sloping white sand beaches fringed by palm trees, Saba rears up out of the water, its highest volcanic peaks covered in rainforest and wrapped in cloud, like a modern-day Skull Island. Here the surrounding waters were a deep sapphire blue, and the swells broke violently on a rocky shoreline. Anchoring is prohibited, both by local regulation and the impossibility of running out enough chain and rope to secure a sailboat in these depths. We tied up instead to a buoy in the protected waters of a marine park. Once ashore I was relieved to encounter, not King Kong, but the friendly inhabitants of this hiker’s and diver’s paradise, many of whom are descendants of its original Dutch and Irish colonizers. From a sailing perspective, this was the exact opposite of the traditional tourist islands; here were the coveted solitude, the rugged circumstances,the sapphire blue water surrounding us.







After three days of rainforest hiking and scuba diving, we set off for Nevis, and I was proud to bear the longish sail,12 hours, better this time. No plastic bags or dashes to the toilet. But perhaps my pride was ill-founded as, I must admit, I popped a sea-sickness pill and slept soundly through it all. I awoke to find that we had anchored in front of Nevis’s famous Sunshine bar, which is a must for visitors and a favorite hangout for locals. That evening, after imbibing a second and further rounds, we learned why their signature cocktail is called the “Killer Bee.” In the waning sunshine, we sat and admired the pretty beach and, nearby, the harmonious outlines of the only Four Seasons Hotel in the Caribbean. Sipping cocktails next to us was an American couple who were guests there. Being fans of the unmistakable “Four Seasons touch,” and in the thrall of the boozy camaraderie brought on by the Killer Bees, we asked about their current accommodations. Sadly, although they loved the food and the common facilities, they reported the hotel rooms had fallen prey to the creeping decay that is all too common in the Caribbean—the untiring work of the salty “sea blast” coupled with relentless humidity and lackluster maintenance.

The next day, after visiting the wonderful botanical gardens owned and run by the Douglas family—which includes a pleasant Thai restaurant not to be missed for lunch, snacks, or an iced coffee—we dressed with studied but casual elegance and weaved our way by dinghy through the anchored sailboats to the dock of the Four Seasons. From there, it was a short golf cart ride to the hotel’s beachsideMango restaurant. After a scrumptious meal and some stargazing and post-dinner drinks, we nodded our heads in approval and ambled back to our dinghy. On our way back to Jangles, we took a quick detour to inspect a large whitemega-yacht with a central structure that loomed at least five stories above its deck. Ian said it reminded him of the submarineNautilus, butI insisted on referring to it instead as Moby Dick. A little on-line research revealed it to be a billionaire oligarch’s mega-yacht of eccentric design.




















The next day we hoisted anchor for another longish sail. St. Lucia was our intended destination, but, due to wind changes and a slight electrical hitch, Captain Ian decided to anchor in Little Bay, Montserrat, for the night. We didn’t venture ashore but watched the sunset from the deck, listening to music and happily sipping cold drinks. Then came our evening meal which, enjoying a respite from sea-sickness, I proudly prepared: a fresh salad topped with spicy giant prawns and such local produce as avocado, cucumber, mango, and cashews. We happily rounded out the evening by watching a movie from Ian’s well-stocked video library and playing our now-traditional game of Scrabble, after which it was all hands to bed and lights out.

Ian and my husband were up at dawn to weigh anchor and resume our 207-mile sail to St. Lucia. The next 26 hours alternated between skimming smoothly over calm waters partly sheltered from wind and waves as we passed in turn by the islands of Guadeloupe, Dominica, and Martinique and pounding roughly through the waves as we traversed the deep-water channels between the islands and took the full brunt of the swell from the Atlantic ocean and the unseasonably strong, easterly winds. To ward off bouts of nausea, I focused on helping out on deck while also expanding my nautical vocabulary; the side of an island sheltered from the wind was called the “lee” while the periodic poundings we received were due to us taking the large swells “on the beam.”Soon, I reflected, I would master enough of the jargon to swap seafaring tales with the best of them!

Finally, in the early morning, we docked at the large and well-equipped Rodney Bay Marina in St. Lucia. Here we stayed for four nights, attending to boat maintenance and sampling some of the excellent local restaurants—Big Chef is highly recommended for lovers of steak. We then made a short and pleasant sailto the postcard-like Marigot Bay, just south of the capital, Castries. We duly celebrated our good fortune and reflected on the serendipity of life; this was the exact place where my husband and I had first met Ian and his lovely wife, and where the idea of our sailing adventure was born just six months previously.

After a tranquil night anchored in Marigot Bay, an eight-hour sail took us to Bequia in the Grenadines. As we anchored in the main harbor, Port Elizabeth,a local fisherman approached waving a live lobster and pointing to a bucket in his boat where many more of the tasty crustaceans squirmed away what were likely to be their last hours. We did indeed succumb to temptation and sacrificed three choice specimens in an outstanding barbequed lobster feast. We closed out our perfect day with another game of Scrabble and then turned in. We knew we had a surprise in store the next day and wanted to conserve our energy.

In the morning, Ian’s eyes were sparkling with ill-suppressed anticipation; from his earlier experiences cruising through the Grenadines, he knew our jaws were about to drop at the sight of our next destination. The Tobago Cays, which we reached after a few hours of sailing in perfect weather conditions, are probably one of the most spectacular sights I have ever beheld. To say they presented fifty shades of blue is to underestimate the breadth of nature’s palette in this particular corner of paradise. By this time I had learned to appreciate the changing colors of the sea and couldn’t understand how I had ever thought it could be boring to sit and contemplate its never-ending variations. Now the experience was taken to a whole new level; it was almost too beautiful to be real.

Ian then told me he was delighted that I found so much art in the varying colors of the water, but there was more to it than mere aesthetics; studying the different shades of blue had a more prosaic and practical side. Before the advent of depth-finders and other sophisticated navigational tools, it was essential for sailors to be able to correlate water color and depth. To be out just a few shades might mean the difference between a safe passage and running aground, with potentially disastrous consequences. Even now, every self-respecting sailor knew his/her palette, and many of the older and more experienced skippers trusted water color over electronic gadgets to guide them safely through tricky waters.

We anchored near the Cays’ turtle sanctuary, watching heads pop up and following the dark silhouette of turtle shells as they surfaced occasionally before diving down to feed or take a siesta on the seabed. Jumping into the water for a swim or snorkel often attracted the attention of these friendly reptiles, and they would approach peacefully to inspect us as we paddled about.


100_2756We spent two days of utter bliss in the Cays, with fresh produce arriving at our “boat-step” thanks to the local water taxis. We even had the luxury of ice for our drinks, although a serious price was exacted for it. Ian swore that by the time he next returned to the Cays, Jangles would be equipped with her own ice-maker.








All too soon we left Tobago Cays. Stopping first at Union Island to deal with customs and immigration, we then moored at Petit Saint Vincent Island for lunch. This tiny island is another paradise on earth. It boasts a truly luxurious resort for those with hefty wallets. But even if visitors choose not to stay overnight, they can enjoy a superb lunch in the island’s perfectly charming beach restaurant. Indeed, our “lunch” lasted until 5 pm, turning rather more liquid than we had intended. A vote was taken, and it was agreed unanimously that we were nevertheless sea-worthy. So off we sailed to Sandy Island, near the coast of Carriacou, where the men, slightly tipsy and heavy with food, smoothly executed the feat of mooring in pitch dark.

The next morning was cloudy and windy. Nevertheless I decided to go for a swim before we left Sandy Island, which, appearing in the light of day, consisted of a single strip of beautiful beach. I duly battled with the elements for forty-five minutes and arrived back at the boat with fogged-up goggles that prevented me from noticing Ian and my husband, whose anxious and disapproving faces told me it might have been imprudent of me to go for a swim alone under such circumstances. Repentant but refreshed, I whipped up an omelet for them before our final long sail began.

A full-day sail from Sandy Island took us to St. George’s, on the southern tip of Grenada, by late afternoon. Ian took us on a quick detour into the harbor, said to be one of the Caribbean’s prettiest, so we could admire the pastel-colored colonial style buildings on the waterfront and see the fort guarding the entrance. Our plan had been to anchor off nearby Grande Anse Beach, a two-kilometer expanse of white sand and aquamarine water. But a decision was made to press on with a night sail to Trinidad. This passage over open water is known to provide a bumpy ride, even under ideal conditions, but the weather reports were good and spirits were high. So on we went. The sail really was a rough ride, but, as if by miracle, not only did I bear it without getting sick, I actually managed to cook our evening meal while we were under full sail and riding the swells south of Grenada. For those who haven’t been inside a sailboat on open water,they can’t fully appreciate this feat. It means dealing with boiling water, open flames on the gas stove and bottles, knives and glasses rattling and occasionally flying about, all as the cook stands balanced like a surfer in the middle of the galley. Being a catamaran, Jangles didn’tpresent the additional difficulty of heeling to one side or another, but it was a technically challenging experience nonetheless. The end result, a pasta Bolognese, was very much praised. I felt I had come a long way in my few weeks on board. On my first serious sailing excursion, from BVI to St. Martin, I had been a more or less inert piece of luggage, horizontally nursing my nausea and incapable of even the slightest activity. Now I was a fully functioning crew member contributing to the well-being of my shipmates.

In Chagaramas,Trinidad, Jangles was to be hauled out and dry-docked for several months while Ian returned home to attend to some personal matters and be reunited with his family. But he spoke already of the day in the not-too-distant future when he would return to re-launch Jangles and sail the islands again.


As we waited for Jangles to be ushered into the slip from which the massive crane would lift her and carry her to a temporary resting place on wooden blocks and trusses, I gazed at the harbor. Here the water was a murky brown, with sheen of diesel and oil floating on the surface. I looked at it with a sinking heart; I didn’t want this trip to be over. It seemed this sailing business had me hooked after all. I wanted to be back on the sea.

I wanted my fifty shades of blue.

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