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Caribbean Island Hopping Aboard a Four-Masted Ship

Our writer cruises into a bygone era aboard the Sea Cloud , an all-hands windjammer.

Motoring off the coast of Soufrière

Motoring off the coast of Soufrière, where St. Lucia’s Pitons rise dramatically from the water.

I’m sipping a morning coffee on the veranda of my winter rental cottage, overlooking Grenada’s Grand Anse Bay, when I spot a four-masted barque looming over the horizon. Her royals and topgallants appear first, followed by her upper and lower topsails. It’s the 360-foot Sea Cloud, approaching the capital of St. George’s like a vision from an antique maritime painting. As she gets closer, I count more than 20 billowing white sails driving her forward at about five knots under a moderate east-northeasterly wind.

Sea Cloud's golden eagle

Sea Cloud’s golden eagle cuts a fine figurehead.

The sailor in me is excited. I’m scheduled to join her that evening and spend the next few days and nights aboard the square-rigger, sailing north through St. Vincent and the Grenadines to St. Lucia and eastward to Barbados. This is an area I’m familiar with, having navigated it many times – on much smaller yachts – since the 1970s.

RELATED: 5 Things to Do in the Eastern Caribbean 

The Windward Islands, particularly St. Lucia to Grenada, are the best cruising waters of the Caribbean, thanks to predictable easterly trade winds, fair seas and sheltered bays in which to drop anchor and hang out with fellow sailors for a bite and a drink. Now, instead of being a skipper, navigator or deckhand (not to mention bartender), I’m visiting these islands as a pampered guest aboard what must be the world’s most beautiful passenger-carrying windjammer. Keeping my hands off the sheets and winch handles is a change of pace I’m sure I’ll get used to, along with the homemade mango sorbet.

Left: Simon Kwinta; Right: Passengers on a Zodiac

Left to right: Hotel manager Simon Kwinta has clocked 30 years on the ship; passengers are ferried to and from shore aboard a Zodiac.

By nightfall, Sea Cloud is anchored a mile out in the bay, lit up like a majestic Christmas tree, with lights hung from her towering masts and yardarms. The ship’s tender ferries me out, we pull alongside the white hull, and the purser’s assistant welcomes me aboard. I spend my first hours wandering the teak decks, marvelling at the polished brass and bronze fittings, neatly flemished lines, ornate woodwork and intricate rigging with anti-chafing baggy wrinkles that are handwoven from hemp, just as it was done centuries earlier. Even the bridge retains the mounted brass binnacle and engine-order telegraph installed when the ship was launched in the 1930s, though it is now updated with 21st- century navigation and communication systems. When the two-ton anchor weighs at midnight, most of the other 58 guests retire to their cabins. I’m too pumped to sleep: It’s always been my dream to travel on a tall ship. As we motor north – the sails are normally hoisted only during the day – I stay out on deck, musing across a time warp to more than 400 years earlier when similar ships brought waves of Spanish, French, British, Dutch and Portuguese colonizers to many of these islands. They were far less opulent, and far less seaworthy, than this elegant five-star cruise ship gliding through the warm air of the tropics.

Oak-panelled dining room

Evening service in the oak-panelled dining room is like supping back in time.

Like a sailor consigned to the all-night watch, I catch only a few hours of rest in my portside cabin before I’m back for more at dawn, when the ship’s captain, Vladimir Pushkarev, an affable 48-year-old Belarusian in neatly pressed whites, orders the sails hoisted. It’s a stunning choreography to take in: 18 young men and women, many of whom trained on famous navy ships in their home countries, scamper up the ratlines and crawl out on the yards and yardarms, releasing the buntlines and unfurling the Duradon canvas sails (most sailcloth these days is synthetic). Below, others operate huge deck winches to trim the billowing square sails to get just the right angle to catch an eight-knot southeasterly breeze. “I love being way up there; I can see forever,” one deckhand says to me as she starts climbing. Watching her silhouette against the sky, the highest upon a yardarm on the 178-foot main mast, I’m feeling both acrophobic and awed.

Left: Cabin No. 1; Right: Climbing the mast

Left to right: Owners’ Cabin No. 1 has golden faucets, marble mantels and Louis XIV-style furnishings befitting a cereal heiress; Mast of ceremonies: Crew members climb up to 178 feet above sea level.

We drop anchor the next day off Union Island’s secluded Chatham Bay for a swim and a beach barbecue of grilled eggplant with Caribbean spices, swordfish steaks and red cabbage salad with papaya. I go ashore again when we anchor off the town of Soufrière, beneath St. Lucia’s majestic Pitons, to check out the Petit Peak Restaurant and Hummingbird Beach Resort, two popular sailor hangouts, which are much as I remember them from years earlier. Mostly, I’m happy to stay on the water, soaking up the ship’s atmosphere. It’s like stepping back in time, down to the lodgings, like the 410-square-foot owners’ suite (designed for Marjorie Merriweather Post and Edward Hutton) with original 1930s gilded decor, marble fireplaces and golden bathroom fixtures. On the broad canopy-covered lido deck, the bar and entertainment centre, the chorus of ship’s officers and crew belt out sea shanties in English, German, Polish and even Tagalog to the accompaniment of the piano player, Peter. We passengers do our best to join the singalong. (The signature Drappier champagne helps.) Besides having no swimming pool, casino, fitness centre or Las Vegas-style floor show, Sea Cloud is television-free. Instead, the ship’s oak-panelled dining room walls are lined with a huge collection of books, including Joseph Conrad’s and Patrick O’Brian’s seafaring novels. It’s ideal reading for a time machine. In fact, I decide to remain on board when we anchor off Port Elizabeth in Admiralty Bay, Bequia, and that’s how Sir James Mitchell, the former prime minister of St. Vincent and the Grenadines, happens to find me when he comes aboard for a tour.


Grenada is a stop on the ship’s Bridgetown to Bridgetown cruise itinerary.

On the evening of our 90-kilometre sail to the island of Bequia, Captain Pushkarev hosts a formal cruise cocktail and dinner, upping the ante on our usual gourmet meals, tea times and midnight snacks. Before the main course hits, there’s king crab with verjus, turbot with vanilla beurre blanc and a palate-cleansing kir royale sorbet. It’s a far cry from my usual cruising menu, when I only worry about gutting and filleting a fish or opening a can of Spam without slicing a finger. Fortunately, my seat at one of the dining room’s eight communal tables puts me next to a friendly doctor from Switzerland, and she’s happy to advise me on which of the many forks, knives and spoons are appropriate for the courses placed in front of me.

Left: telegraph; right: chef Uwe Pöhlmann

Left to right: The brass engine-order telegraph is one of the original fixtures on the bridge; it’s a catch for chef Uwe Pöhlmann.

I wander the decks after supper, gazing at the crystal necklace of constellations high above the ship’s swaying rigging, feeling the slight roll of the deck beneath my feet and hearing the slop of waves against the hull. Unlike floating resorts with 3,000 or more passengers, everybody gets to know everybody on a small ship like this – it’s an international family feeling, with the crew alone representing 12 different countries. I take a pause with several off-duty sailors, gathered on the foredeck near the crew’s quarters in the fo’c’sle, and get to chatting with the chief carpenter, who tells me that Sea Cloud, with her antique woodwork and complex rigging, is more challenging than any merchant vessel or cruise liner he’s ever worked on. The crew of 61 and the 64 guests (maximum) all have one common interest: to travel as in golden days of old.

Blue Lagoon

The cushy lounge area at the stern is known as the Blue Lagoon.

Shortly before sunset, as we’re sailing to our final destination of Bridgetown, Barbados, a barquetine, the Star Clipper, passes us to port, with each skipper giving a salutary blast of the horn. A deckhand beside me scoffs, “That’s a push-button ship,” by which he means that of the few passenger-carrying windjammers plying the Caribbean and European seas, only Sea Cloud is sailed entirely “by hands.” Others may look authentic, but the sails are largely set by computer-controlled servomotors rather than by proud human deckhands.

All hands on deck

It’s all hands on deck aboard this 1930s windjammer.

I spend my last night again on deck with a few fellow passengers, sprawled across the turquoise pillows of the Blue Lagoon, a relaxation area at the ship’s stern. We’re trying to identify the stars high in the sky and to figure out the proper names of fixtures on the mizzen mast and shrouds. This old sea dog is learning some new tricks.

For more information or to book a trip aboard the Sea Cloud, visit

This ship has sailed

Leaving St. Lucia with the wind in her 32 sails

Nautical and nice: Leaving St. Lucia with the wind in her 32 sails.

Built in 1931 for breakfast cereal heiress Marjorie Merriweather Post and her Wall Street tycoon husband, Edward Hutton, Sea Cloud was the world’s largest and most expensive private yacht of its time.

The ship was owned by the Dominican Republic dictator Rafael Trujillo and his playboy son who used it as a floating party house off Long Beach, California.

After Trujillo’s assassination in 1961, the ship was abandoned and left to rot on the eastern end of the Panama Canal.

After Trujillo’s assassination in 1961, the ship was abandoned and left to rot on the eastern end of the Panama Canal.



Comments… or add another

Jean Todd

Sunday, January 17th 2016 10:55
This is so cool I can't even believe it. It must be the greatest adventure to sail on this ship.


Sunday, January 17th 2016 16:01
Is there a contact / website to explore booking this trip?
What was the price range?

Denis Conway

Monday, January 18th 2016 08:02
HI, I would be interested in knowing more about how to book one of these sailing tours and what the cost would be per couple..with thanks


Monday, January 18th 2016 16:21

Blair McRobie

Monday, January 18th 2016 17:40
How to book?
What is cost per couple per week?

Christine Cliche

Monday, January 18th 2016 20:20
I would like more info on this sailing yacht and prices per couple

S.M. Haycock

Monday, January 18th 2016 22:53
I am interested in dates of departure, how many the ship accommodates, the size of the cabins, washroom facilities, etc. And of course - the cost. please send me more info.
I embarked on a Windjammer cruise at the beginning of my honeymoon in Dec. 1976. It was a disaster. The ship never left port and we abandoned ship in St. Lucia and flew to Barbados where we continued our honeymoon at the Hilton. In this case, the ship was not clean and it ran out of water and one engine was down, so rather than wait around for a part to be delivered, we went a shore with the 2nd mate, had to jump into the water. We walked up the sand to the Holiday Inn. We looked like we belonged in an American Express Ad - don't leave home without it. LOL But I'm willing to try it again in the hope that things have greatly improved since 1976.

Julia Eble

Friday, January 22nd 2016 03:19
Good day, you can find detailed information on


Friday, January 22nd 2016 09:50
can you send me some information about the excursion, re the dates , price , where the ship sail from.


shirley hollas

Thursday, January 28th 2016 09:25
would love to go on vacation like this all of the pictures are georgous and am sure the food is to die for12

shirley hollas

Thursday, January 28th 2016 09:26
have never had much luck winning anything , but would love this
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