Skip to main content

Schoonermen in the Caribbean 600


Eleonora reaches out toward open water under full sail shortly after the start

When Alexander Cochran ordered the 135ft steel schooner Westward from the board of Nathaniel Herreshoff in 1909, he had no notion his vision would bring together an eclectic bunch of sailors to race in the Eastern Caribbean over a century later. Under the command of legendary Scottish Captain Charlie Barr, Westward swept across the Atlantic in 1910 to take 11 firsts in 11 starts against the finest opposition Europe could produce, including the all-conquering Royal Yacht Britannia and the German Kaiser’s Nordstern.

Ninety years to the day after the launch of Westward, a perfect replica came down the ways at the Van der Graaf Shipyard in Holland. Her name was Eleonora. Like Westward before her, Eleonora was created to race, but, apart from gatherings of classics, competition is hard to find in the 21st century over courses of a scale that suits her. Round-the-cans afternoon dashes are a serious workout for crews handling spinnakers and gollywobblers the size of Walmart parking lots; the boat is hardly into her stride before all the interesting stuff has to come back down again for the next leg.

The RORC Caribbean 600, on the other hand, is tailor-made for big schooners. Set across the northeast tradewinds among the islands around Antigua, it features reaches of up to 150 miles, one or two stiff beats and the odd shortish run. Regardless of winning or losing, 600 miles of glorious sailing against top boats, both ancient and modern, is a promise no sailor could turn down. So when the call came to join Eleonora, I threw my busy winter diary out of the nearest porthole and hopped a jet to the islands.


I arrived three days before the start to find the yacht already under the Royal Yacht Squadron burgee of David Aisher, a friend of the owner. The crew of 28 under Captain Brendan McCoy was a mix of guests and professionals. Levels of competence ranged from the keen but relatively inexperienced to the tough, fit and deeply experienced nine men and women comprising the permanent crew, which included a great-grandson of Charlie Barr himself.

The ship’s complement also included a group of athletic professionals brought in to beef up the numbers, keep the amateurs from maiming themselves and help whip us into a team that, by the time we hit the start line three days later, was working remarkably well together. One thing was for sure: with 12,000ft2 of sail, either to drive you or smother you with extreme violence, there was no room on deck for passengers.

Despite the general sense of optimism, rum-fueled parties and a keen edge of competitiveness, a cloud threatened to block our view of the Caribbean sunshine. Above all, what a schooner needs is wind. And while February in the Eastern Caribbean is usually the nearest you can get to guaranteed breeze, this year the unthinkable happened in the form of a long, trailing front that sagged down from the North Atlantic and messed up the trades. It didn’t get fully operational until the day of our start. But then, along with a slack low-pressure system forming down its edge, it performed tricks with the wind you’d only expect to see coming out of a conjuror’s hat.

The outlook wasn’t good for the heavy classics, to say the least. And with light winds predicted for the closing stages of the race, we knew we couldn’t compete against today’s featherweight flyers, although we could still have a private contest with Adela, the other schooner. That said, Adela carries a modern rig and is longer even than Eleonora’s 160ft of sparred length, so she was going to be faster over the water. Nonetheless, if the handicappers had done their sums and we worked our boat till we dropped, we were in with a chance of pipping her at the results table.

In the short term, the start line also promised to be a high-stress scene, because handling a gaff schooner under full sail is a complex business. Precedent has already been set for part of Eleonora’s rig going over the side if one of the runners is missed, and relatively maneuverable boats that failed to understand our issues might call starboard on us with unhappy results. The same concerns could well aggravate matters if we got mixed up with Adela, so the two skippers agreed on a startline policy: specifically, since Adela would be quicker than us and not setting topsails or a fisherman staysail meant she could more or less “flop over” if challenged, we agreed that she should cross the line first with us close behind. We would also both hang back to keep clear of smaller craft.

Adhering to this plan, we subsequently got away without incident along the south coast of Antigua, close-hauled in a brisk breeze from the east, watching open-mouthed as Phaedo3 and Maserati, the two flying MOD70 trimarans, shot past us to disappear from our lives in minutes. We’d given Adela a minute or so, but with a waterline of around 100ft, 600 miles would leave us plenty of time to make it up. On the wind, though, Adela soon opened a commanding lead, keeping close inshore where she could tack as often as she wanted.

Unfortunately, since coming about aboard a full-on gaff schooner like Eleonora involves a good deal more than just passing a headsail across the foredeck, we had to stand far out on one long board. Granted, the main jackyard topsail with its massive 60ft luff spar can stay put. But the fore gaff topsail and the fisherman staysail have to be dropped before the boat can be brought to the wind, since both are set in the area between the masts and would otherwise tangle with the staying aloft. Therefore, as a first step in preparation for tacking, the foremast hands all gather to leeward while the topsail halyard and sheet are let go and they then grab the sail as it comes down and prepare it for rehoisting on the other side.

The crew prepares to hoist a deck-load of sail as the wind falls light

The crew prepares to hoist a deck-load of sail as the wind falls light

While this is going on, a midships team also spreads out along the deck under the foreboom ready to smother the fisherman as its two halyards are eased. For readers who don’t know about fishermen, this four-cornered sail is set flying, with the fore upper corner landing where the foremast is doubled with the fore topmast, and the aft upper corner hoisted to the main topmast. The sheet is then led inboard from the aft lower corner to a sheave far out on the main boom and the tack is brought down to the foremast at deck level. There’s a wide variety of possibilities for dangerous mistakes, but somehow, under the mate’s eagle eye, it’s controlled and shoved under the boom for hoisting after the tack is complete. 

Once these upper sails are on deck, the yacht can tack, a relatively straightforward procedure except for the two sets of runners, which are intimidating in their sheer weight, and yet were operated by the two stewardesses and the cook, aided and abetted by a retired English colonel. In order to set the right sheeting angle for the three headsails afterward, the bowman stands on end of the bowsprit using hand signs that refer to each sail’s designated number. (Nobody shouts on Eleonora except, occasionally, the mate when he needs to gee up the spinnaker sheet crew.) The jib topsail is “one,” the jib is “two,” and the staysail is “three.” The bowman, known mysteriously as “the Nipper,” even though he is actually the mate of the schooner Elena on loan to us for the race, holds up one finger, and signs to heave in the jib top. Then it’s two fingers, and so on. The sails are not slammed in tight straight off, but eased a touch while the schooner gathers way. Once she is up to 10 knots or so, she comes up slowly and the sails are sheeted in until she is making around 45 degrees to the true wind.

Soon afterward, sheets are eased again, the fisherman comes down and the gollywobbler goes up as we round Antigua and head north toward Barbuda. The gollywobbler is a sort of giant fisherman that completely fills the gap between the masts. It overlaps the mainsail like a giant genoa, and its power is fearsome. As the reach broadened, the spinnaker followed, set in wool stops to keep it under control until the sheet is hauled aft, at which time it bursts open. Trimming it is just like on any other boat, with a man sighting from the weather rail and the trimmer working the winch. The only difference is the scale.

Various maneuvers followed as night fell between Barbuda and Nevis. Every so often a foul-up aloft would mean one of the young men had to fly up on a harness to perform seemingly impossible feats of strength and gymnastics: including the dreaded walk out along the gaff to the extreme end where a topsail sheet had whipped around the spar and could not be freed any other way.

As we rounded the island where Admiral Nelson met his ill-starred wife, Frances, the wind had come right into the west, clean on the nose, and fallen light. We beat past the brightly lit shoreline in the dark and fetched off toward Saba, 50 miles to the northwest as the watch changed at 0200. When the watch below clattered back on deck at 0800 we were reaching toward St. Martin under spinnaker and “golly.” Up to weather boiled the blackest of squalls, and the rain started falling; the front had arrived. We were hardly kitted up before it was hammering down in a solid wall of water, and the wind had filled in for real so that all hands were soon tackling the gollywobbler. Along with 10 others, I was scrabbling at its craziness from the windward side. One of the hands, Colin, was hammering it into submission from leeward. My head got in his way, and I sported a fine black eye for the rest of the trip. The chief stewardess remarked that it looked as though I’d forgotten my eyeshadow on the starboard side.

The next part of the course emphasized the insanity of the conditions, which were by now 180 degrees adrift from normal. Boats typically reach past St. Martin and then thrash up to the weather end of the Anguilla Channel. However, after the rain—which poured down so densely it cut visibility to 100 yards—eased off, the breeze kicked in again from the southwest, and we spent the second afternoon beating up to the windward end of St. Martin.

Plenty of breeze and sea room make for ideal schooner-sailing conditions as the sun goes down at the close of the first day of the race

Plenty of breeze and sea room make for ideal schooner-sailing conditions as the sun goes down at the close of the first day of the race

Here, at last, we bore away and set every stitch we had. The crew rejoiced, and the watch below tumbled up on deck as we scorched down that sound at 14 knots, eating up every yacht in our path. Respectable raceboats swam briefly into our sights and were trounced one after another as we romped along, scuppers running with clear Caribbean water, the whole rig roaring a tune of unbridled power. It was glorious while it lasted, but all things must end, and by the time another star-carpeted night had wheeled by we were becalmed between Montserrat and the south end of Guadeloupe.

Alas, this was the hole in the wind threatened by the weather people; the radio told of a huge boat park between Guadeloupe and the Saintes, and the forecast offered little consolation. A modern yacht becalmed in a seaway can drop her headsail, strap in the main and suffer little more than an annoyance. For us, though, it was a very different story. The racket from aloft was deafening as the gaffs screamed in protest with each roll. We took in the fisherman and bagged the spinnaker, but the clatter went on. The jackyarder was suffering most, with its huge club yard being munched by the gaff spans at every lurch of the rig. The afterguard did its calculations and decided that even if we sat there waiting for the wind that was due to arrive late the next day, we still wouldn’t be back in time for the prize giving. The damage the yacht was suffering was painful to watch—and hear—so we dropped everything, started the engine and called it a day. Adela retired soon afterward.

Of course, all hands were disappointed at not being able to reach around the entire course at high-speed, as would have been our delight had the trades not failed. But there’s more to life than winning a yacht race. Sometimes it’s enough just to be at sea on a world-class piece of history with a crew that reignites your faith in the future. As the captain of the New Bedford whaler remarked when the owners chastised him for returning home with an empty hold: “Remember the Bible says, blessed are they who seek. We’ve no oil onboard, but we’ve had a damn good sail.” 

Tom Cunliffe sails his Mason 44 in the North Atlantic and Baltic. He is the author of many books, including the recently published The Complete Ocean Skipper

June 2017




The Extraordinary Life and Mysterious Disappearance of Thomas Thor Tangvald

The first boat Thomas Tangvald ever owned was just 22 feet long. She was an odd craft, a narrow plywood scow with a flat bottom, leeboards on either side, and square ends—little more than a daysailer with a rotting deck and tiny cabinhouse tacked on. Thomas paid just $200 for more


USVI Charter Yacht Show Showcases a Flourishing Industry

As the U.S. Virgin Islands continues to attract sailors seeking to charter and explore the pristine territory on their own, the immense growth and expanded options for a crewed yacht or term charters have exploded here over the past five years. Last week, the USVI Charter more


Personal Locator Beacon Wins Top Design Award

The Ocean Signal RescueME PLB3 AIS Personal Locator took top honors at the 2022 DAME Design Awards, while Aceleron Essential, a cobalt-free lithium-iron phosphate battery with replaceable and upgradeable parts, won the first DAME Environmental Design Award. Announced each year more


EPIRB in the Golden Globe Race

Tapio Lehtinen’s boat sank early this morning southeast of South Africa while racing the Golden Globe Race, a faithfully low-tech reproduction of the 1968 Sunday Times Golden Globe. The boat went down quickly and stern-first according to the skipper’s emergency transmissions. more


Victory, Tragedy in the Route du Rhum

The 2022 Route du Rhum was a highly anticipated event in the ocean racing calendar, but few could have predicted exactly how challenging, dramatic, and tragic it would ultimately prove. French yachtsman Charles Caudrelier took home gold aboard the Ultim maxi trimaran Maxi Edmond more


Boat Review: Lyman-Morse LM46

Lyman-Morse has been building fine yachts in Thomaston, Maine, ever since Cabot Lyman first joined forces with Roger Morse back in 1978. With experience creating and modifying boats built of various materials, backed by its own in-house fabrication facility, the firm has more


Know-how: All-new Battery Tech

Until very recently, the batteries in sailboats used some form of lead-acid chemistry to store energy. Different manufacturers used different techniques and materials, but in the end, the chemistry and the process by which the batteries charge and discharge electricity remained more


At the Helm: When Things Go Sideways

I don’t like sea stories. My number one goal on every passage is to get the crew back in one piece. My number two goal is to get the boat back in one piece as well. If I can’t do both, I’ll take the former. Do this long enough, though, and things are going to happen, no matter more