Windward Isle Wonderland

Ten days, seven islands and one blazing boat combine for the best of sailing and sightseeing (Published Fall 2014)

I have to admit I was skeptical when I looked at the chart and realized that we’d be sailing over 300 miles on a round trip ten-day charter in the Windward Islands. Covering that much distance didn’t leave much time to actually experience the sights, sounds and flavors of this part of the Caribbean. However, the promise of a nearly new and equipment-packed Catana 47 making cat tracks through the easterly trades did sound like the perfect sailing adventure, so I was all in.

Dream Yacht Charters in Le Marin, Martinique was our point of departure and the sheer number of new cats on the dock gave me goose bumps. There seemed to be a veritable fleet of Catanas and we stepped aboard a shiny 47-footer named Rhin. In the walk-through I relished the amount of equipment onboard. There were daggerboards, electric winches, air conditioning, a genset, a watermaker and a gennaker on a furler. This was no dumbed-down charter boat. We were going cruising in style and comfort. Of course, all those systems added complexity that I would need to manage over the next week and a half so it was time to pay attention.
boatboy beqsalesguys

Most any time is a good time to be in the Windward Islands since temperatures range from the 70s in winter to the 90s in the summer and the tradewinds blow a refreshing breeze daily. Our journey was between 14 and 12 degrees north latitude and about 61 degrees west longitude, which makes it technically still in the hurricane belt, but since we visited in April, there wasn’t much to worry about.

Our first day of sailing landed us in Marigot Bay, a very protected small harbor on St. Lucia. Despite the downpour that emphasized why this island is so lush, the place looked like a Caribbean movie set with mooring balls for cruising boats on either side of the harbor and small colorful houses and docks farther in. The more intrepid among us visited other boats by swimming from one to the other while the rest made a delicious dinner aboard. St. Lucia is striking and the next morning, even as we rounded the spectacular Pitons (two volcanic plugs on the western coastline reaching almost 2,400 feet in the air), I made a note to come back sometime for land-based exploration.


The next 70-mile leg was past St. Vincent and all the way down to Bequia, the northern most in the chain of gem-like islands that make up the Grenadines. You’ll notice two things immediately about Bequia: First, you’re mispronouncing the name, it’s Bek-way; and second, the friendliest people in the West Indies seem to congregate on this, the largest of the Grenadines.

Bequia’s expansive Admiralty Bay off Port Elizabeth provides sheltered anchoring and lots of mooring balls. Here, we had our first encounter with “boat boy” culture where men (and women) come out in their small boats to assist cruisers. They’re quintessential entrepreneurs so we took care of them with modest tip money and they took care of us by helping to tie us to moorings, bringing fresh baked goods in the morning and even hauling away trash.

It’s surprising how much there is to do on an island of seven square miles. A taxi ride introduced us to our driver Sally who told us she has to get a brake job every year and after seeing the hilly roads of the island, I didn’t doubt it. She took us to the windward side to meet     Orton “Brother” King who has spent 19 years on Bequia tending Hawksbill turtles. He rears hatchlings at his farm until they’re old enough to survive on their own at age three. I learned that a turtle can not only feel a good back scratching through its shell, but clearly enjoys it and will happily splash about for as long as you care to do the scratching.

Shopping in town is colorful—literally. Bright T-shirts flap in the breeze outside gift shops and street vendors offer everything from fruit and locally made jewelry to carved coconut boats. Strolling down Belmont Walkway, a stone path lapped by the waves of the bay, is like window-shopping for a place to relax as cafes and bars line up one right after the other. The Whaleboner Bar has a bar, stools and an entrance made of whale vertebrae. And for terrific pizza, Mac’s is a must.

We waved a reluctant goodbye to Bequia and set a course south. After a 30-mile beam reach we ducked into Saltwhistle Bay on Mayreau Island planning to hop over to the Tobago Cays the following day. With the sun low in the sky, the water was reflective so we couldn’t make out the depths and decided not to enter the area of Horseshoe Reef until the next morning.


When you think of aquamarine water, white sand beaches and the occasional palm tree leaning out over the ocean, you may be thinking of the Tobago Cays. These small islands are the stuff postcards are made of, a seemingly Photoshopped paradise with kaleidoscope colors where you can drop out of civilization for just a little while.

Four small islands hide in the protected waters of the reef, the hedonistic set for Johnny Depp’s “Pirates of the Caribbean” and “Dead Man’s Chest.” When snorkeling in the turtle preserve near Baradel Island, we’d be flanked by two to four turtles at a time and we could even hear them chewing the grass on the bottom.


The Tobago Cays were designated a Marine National Park in 1998, so rangers collect $10 EC (Eastern Caribbean dollar which is about 40 cents U.S.) per person per day. Anchoring in 20 feet is easy and we settled into a lazy day followed by a perfect beach barbeque organized by the boat boys. A storm moved in that night but the party went on in the drizzle under a string of bare light bulbs with kettles of the kind of conch chowder that still makes my mouth water even today.

With the sun high in the sky the next morning, we threaded our way through the southern reef on our way to Union Island only three miles away. The highest peak, Mt. Parnassus, is nearly 900 feet high so you can’t miss it. The main town of Clifton provides great shopping with an open-air produce market and several grocery stores. Janti’s Happy Island near the harbor can only be reached via dinghy because this tiny spit was built on the reef out of thousands of conch shells gathered by Janti, the owner. Talk about creating value out of nothing. Today, it’s the spot for a sundowner cocktail with friends new and old alike.

That afternoon, strong trades made us seek shelter in Chatham Bay on the western side of the island. Dinner was at a shack called Shark Attack that advertised “Figure Licking Good Food.”  No “figures” were licked that night, as far as I know.


We had sailed as far south as we dared given our schedule and it was time to loop back and visit St. Vincent on our way north. St. Vincent is a hilly, rugged island less than 20 miles long and topped by Soufriere, a 3,000-foot volcano that last erupted in 1979. We picked up a mooring in Young Island Cut and dinghied around the corner to a high stump of an island that is home to Fort Duvernette. Several cannons were hauled 200 feet up the rock to defend Calliaqua Bay from whoever may have been attacking. As I climbed the rocky stairs I completely understood why nobody ever moved the armaments back down.

We booked a day tour that started with Fort Charlotte atop the main city of Kingstown. It now houses a women’s prison where at the time of my visit, there were 16 inmates. The guide was sure to point out that by contrast, the men’s prison, located on the northern tip of the island, has 200 occupants. I didn’t understand whether the local population was just less lenient on men or whether these females were just particularly bad to have landed here.

A two-hour tour in town took us through the vast botanical garden with the self-titled “Professor,” a local who had spent 30 years as a guide. I’m flora-challenged, barely differentiating a tulip from a turnip, but I found the information as well as its humorous delivery a delight. Who knew that Captain Bligh had brought breadfruit here all the way from the South Pacific, that wax apples are delicious and that the national parrot was so tame that you could hold one on your hand?


Every local has a version of the area’s history and the Professor may have been more imaginative than some. When Columbus plied Caribbean waters, St. Vincent was known by its inhabitants as Hairoun, which means “home of the blessed,” and today is also a brand of a popular local beer. Over the centuries, the Eastern Caribbean was settled by the peaceful Arawak Indians from South America. Subsequently, the war-loving Caribs moved in, killed the men, kept the women and castrated and fattened the children for future feasts. It was a succinct, even if a bit grim, synopsis of the island’s beginnings.

Two hundred years later came the missionaries who didn’t fare well against the Caribs either. Nevertheless, the Europeans kept coming, often on slave ships that wrecked on the nearby reefs. Surviving Africans swam ashore, mixed with the Caribs and created a new group called Black Caribs who, of course, didn’t get along with the original Yellow Caribs. Clearly, this paradise had experienced its share of conflict.

By this time the French and British were also waging scattered battles over the territory as well as fighting with the Caribs who were still fighting each other. Eventually, cannons and muskets prevailed and the Black Caribs were rounded up and shipped to Roatan off the coast of Honduras. St. Vincent, which spent much of its time under French rule, then became a part of the British colony of the Windward Islands in 1871. In 1979, St. Vincent and the Grenadines became an independent state within the British Commonwealth. Clearly, there had to be more to the historical details, but we didn’t have the time to do the research and jumped back aboard for the last push north to Martinique.


The Catana 47 was a dream to run. Most days we averaged 25 knots of wind with gusts to 30 and six to eight foot seas. I wouldn’t have wanted new and seasickness-prone sailors on a monohull in those conditions. But a blue water catamaran changes the dynamics aboard even in boisterous weather by staying mostly upright and changing, if not minimizing, the motion so mal de mer is kept at bay.

I quickly learned that with the boards about two thirds of the way down and one reef in the main and jib, I could set the autopilot and the boat took care of itself. We consistently maintained nine to 11 knots of speed on a beam reach. The mainsail was large but the electric winch made swift work of raising it, and with some clever line angles we also used that winch to raise the heavy dinghy and outboard up onto the davits.

The watermaker (which required the genset to run) was a godsend as we luxuriated in unlimited fresh water. I soon learned how to clear the air out of the genset intake lines because although I’d have said we were barely heeling, we did manage to suck air in on almost every sail. It was a small price to pay for daily showers.

It took some time to dial in the daggerboards. I was so concerned with grounding in shallow anchorages that I first raised them all the way when mooring, leaving us with a three foot, seven inch draft. However, the Catana hulls are round on the bottom and tight turns at slow speeds with no keel made us slide around like on a bar of soap. Even just a foot of board down gave the boat enough traction to maneuver in tight quarters.

Our dodge back up to Martinique was a bit of a slog. The wind was forward of the beam and head seas made for slow going. Of course, that just meant that we had the good luck to get more training time under sail which is an added benefit on any charter vacation.

When people ask me where to charter for the best sailing, I tell them that a charter is about the destination and meeting the expectations of all those aboard, and that they shouldn’t put too much emphasis on sailing due to packed itineraries, conflicting interests and unpredictable winds. But on this Windward Isle excursion, we were fortunate to experience it all: great wind, a terrific boat, friendly locals and some of the most beautiful scenery anywhere. And those 300 miles? They disappeared under our   so easily they left us planning to return soon to visit the dozens of islands we had missed and for more Hairoun, turtles and wacky history.

Zuzana Prochazka is a veteran cruiser and freelance writer. She is based in Southern California.