Racing around paradise

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Prospector is sailing fast, the wind blowing 20 knots on her starboard bow. It’s very dark; the full moon has not yet risen. We’ve just rounded Redonda Rock, a looming, jagged outcropping of an island between Nevis in the West Indies and Montserrat in the Lesser Antilles. Sheeted in tight, standing on the stern, I’m straining to grind in the mainsheet. I can’t believe I’m here.

The writer sailed aboard Prospector, a Farr 60 that has had a great racing career under the names Deep Powder, Carrera, Hissar and Captivity.

Behind me, driving and navigating, are two world-class sailors: Volvo Ocean Race veterans Jonathan “Jono” Swain and Campbell Field. We’re heading to the finish line, and I am exhilarated by the possibility that our results will reflect our focused efforts. We had started the RORC Caribbean 600 — a 600-mile race around 11 Caribbean islands — 55 hours earlier.

Twelve of my fellow mates are hiked out on the rail. The whitecapped waves roll endlessly on, luminescent against the night sky. This is a sailing moment to savor forever.

The participating yachts are wonderfully diverse, with the world’s fastest multihulls and monohulls racing alongside Corinthian efforts entered by charter companies such as OnDeck and Global Yacht Racing, which put paying customers on boats.

Walking the docks, I look over the lineup of racing machines and the sailors who will crew them. Of the 69 starting boats, only two are local. Twenty-four countries are represented. The stars berthed here include Comanche, Varuna, Highland Fling XI, Bella Mente, Spookie and La Bete (ex-Rambler). All are available for inspection. I never tire of engaging crewmembers in conversation about their boats. The docks are open to all, day and night.

The two trimarans in the race, Phaedo3 and Concise 10, are MOD70s and sail in their own class. These tris will reach speeds of 40 knots and regularly sail at more than 30 — how far sailing technology has come! Phaedo3’s owner and co-skipper, Lloyd Thornburg, has smashed so many sailing records that one would run out of wind listing all of them. He set a record for the RORC 600 this year, finishing the race in 31 hours, 59 minutes, 4 seconds and breaking the record he set last year by 1 hour, 34 minutes, 26 seconds. “It’s incredible to cross oceans at 28 knots,” says Thornburg. “I love the challenge.”

The boat I am on, Prospector, is a Farr 60 built by Carroll Marine in Rhode Island in 1998. She has had an exceptional racing career under the names Deep Powder, Carrera, Hissar and Captivity. Many great campaigns have been conducted from her decks. Two years ago she was refurbished by a syndicate of sailors from the Shelter Island (New York) Yacht Club with the goal of sailing her in a series of offshores and then a trans-Atlantic race. The goal was met, and Prospector placed second overall in the 2015 Atlantic Ocean Racing Series.

I was aboard because of Tony Rey, who is based in Newport, Rhode Island, and is the head of Cloud10 Racing, a company that runs racing programs for a variety of owners and boats. Cloud10 Racing has partnered with the Camper & Nicholsons yacht brokerage to form a turnkey regatta program in which clients outline their ideal race and boat, and Cloud10 works with C&N to organize the regatta experience.

Working with longtime client Peter Cunningham, Rey found Prospector and put together a team for the RORC 600. He combined this new team with Prospector’s longtime captain, Tery Glackin, and two mates, Quinn Tobin and Scott Tompkins, all of whom hail from Newport. It was then up to Cunningham to bring along some of his experienced sailor friends as additional crewmembers.

I have sailed for more than 30 years, crewed on a delivery from Bermuda to Maine, adventure-sailed to Cape Horn, and regularly cruise my Sabre 38, Sachem, to Nantucket and Martha’s Vineyard, Massachusetts, and Down East Maine. I have participated in scores of regattas and club races, and have dozens of trophies to prove it. Solo daysailing Sachem or an Etchells is my favorite summer activity.

The 600-mile course weaves around 11 beautiful Caribbean islands.

Yet I have nowhere near the abilities of these pro sailors. They reacted to Swain’s directives faster and with more precision than I could even contemplate. They had an instinct for sailing commands because they had performed these maneuvers a hundred times before.

One of the amazing things about sailing in the Caribbean is the constancy of the wind. When the horn sounded for the start of our division, there was lots of wind. And it blew for the 2 days, 14 hours, 7 minutes and 10 seconds we raced. The trade winds are usually east with a northern or southern component — you can count on it. In the lee of the islands, the wind might drop to 12 to 15 knots. Once we were back out in open water, 20-plus knots was the norm.

Thus, the race depended on having the proper sails up and adjusting them for maximum speed, which we accomplished, as we only sailed 20 miles more than the 600-mile course. I didn’t miss the long clearing tacks I’m often forced to make off Rhode Island.

Swain and Field, in consultation with Glackin, decided on the sails to set. Then it was up to the agile, talented foredeck crew to make the changes — quickly and accurately. We must have done 25 or more spinnaker peels, and dropped and hoisted various jibs a score of times. Occasionally, we flew three headsails. We even utilized a Code Zero with its own internal stay and shackles. This was not just unfurling Sachem’s jib, setting it on port and arriving in Cuttyhunk eight hours later. Day and night, heavy sail bags were brought up from below, slotted in, hoisted and sheeted in. At night we wore red-light headlamps so we could see how to run the sheets and lines without affecting our night vision.

The Caribbean is lumpy. Although the waves are not high, averaging 4 to 6 feet, their motion is random. Every moment on board requires a careful think-through. Where am I going to place my hands and feet? I had to brace myself at all times or risk being hurled against something unpleasant. If you ask me how to train for this race, I’d say find a commercial laundry and put yourself in a washing machine for a few hours. It’s so exhausting that almost a week after disembarking I was still sleeping 10-hour nights and napping midday.

In fact, as magical as it is, this dream is also exhausting. Although the watches had scheduled down time, I never really slept; I just passed out in my wet pipe berth — wet because the previous occupant had arrived soaked from sea spray as the boat pounded into the boarding waves. It was pointless to dry off. Like the others, I stopped taking off my outerwear and shoes after the first day. Putting them on and taking them off, amid Prospector’s erratic motion, was just too tiring.

The boat’s constant groaning and banging noises didn’t encourage sleep, either. Every loosening of the mainsheet, as it moved against the winch, emitted a pronounced squeal. Shackles and blocks banged against the deck. At home one would never attempt sleep in a racket like this; on board there was no other choice.

On Prospector, Dave Tank, the foredeck wizard, moved like a ballet dancer. I watched his dexterity with amazement and envy. I thought through every one of my motions, like planning a chess move three steps ahead. I always held tightly to something while I looked for the next handhold. Jumping in anywhere and everywhere, I made myself useful by bringing up empty sail bags for dropped sails, standing in the cabin to pull down the spinnaker when we did a letterbox drop and rebag it, even refilling our water bottles. I ground the pedestal winches like a man possessed — until I thought my shoulder would separate trying to keep up with the behemoth pro grinder we called “CT.”

When it came to gybing the spinnaker, it was all hands on deck. It did not matter whether you were off watch and asleep. Everyone was needed to bring the huge A2 or A3 around. In my experience, this maneuver often leads to serious foul-ups, screaming and recriminations. Not once did this crew make a mistake. The pit man had to respond to a half-dozen lines fed to him, making sure each one was properly led to a winch. All of this happened while under tremendous pressure, both from the forces of the wind and the desire to win the race.

When I wasn’t needed, I sat on the rail and marveled at the majesty of the sea, the clouds and the islands. Sometimes I saw a competitor. Coming on watch with the sunrise as we were running past Dominica, I stared in awe at the cloud-enshrouded island, home to one of nature’s great bio-preserves. This was not my usual morning view.

Prospector placed ninth among 18 boats in our division, IRC Zero. In the words of Cunningham, our skipper, we “punched above our weight.” The majority of boats that finished ahead of us were sailed by crews who practice together constantly.

There was a tremendous camaraderie aboard Prospector, a camaraderie based on respect and admiration for shared sailing skills. Perhaps my favorite moment was the start of the race, fighting for position on the same line with Comanche. It’s not every day you do that.

The RORC Caribbean 600 is now in my blood, and I plan to return next year. This race is a special experience — the boats, rubbing shoulders with some of the greatest sailing talent in the world, the parties, the challenge of the 600-mile course. It is surely this sailor’s dream come true.

This article originally appeared in the May 2016 issue.