Chasing Chichester, 50 Years Later

On the golden anniversary of the first singlehanded transatlantic race, a fleet of determined skippers and their small boats make landfall in Newport, Rhode Island, to complete the third running of the Jester Challenge.

Igor Zaretskiy

In the spirit of healthy competition, Russian Igor Zaretskiy was the first Jester to arrive in Newport. Billy Black

O K, it’s not a race. But if you were one of 22 skippers who left Portsmouth, England, bound for Newport on a sailboat between 20 and 30 feet long, and you found yourself several weeks later sailing neck and neck with another singlehander on converging tracks, well, wouldn’t you want to be the Jester Challenger to get there first?

And so it was, as Igor Zaretskiy, who’d left Portsmouth on May 23 and sailed a northern route across the Atlantic aboard The Grand, a Peterson 25, approached the New England coast a couple of days before his arrival on June 26. Radio reports indicated that his closest challenger, Rory MacDougall on his Wharram Tiki 21-foot catamaran, Cooking Fat, was fast approaching on a more southerly route to Narragansett Bay.

In the end, though, it was Igor who was first to be greeted by Norman Bailey, commodore of the Newport Yacht Club, who also brought Igor a beer and a cigarette. The native of Yaroslavl, Russia, had been smoking tea leaves ever since his tobacco supply was confiscated back in Belarus, so this was a welcomed reward indeed.


By the time we chatted on June 29, the suntanned and smiling 59-year-old had secured Marlboros. “I first read about singlehanding across the Atlantic in the 1960s,” said Igor through our translator, Elena Wilcox. “Since then, I’ve been dreaming about being a participant.”
That’s a four-decade-long dream.

“In Russia, it’s impossible to prepare for such a long race,” explained Igor, a winner of many inland races. A professional builder of wooden boats for 20 years, he’s fruitlessly chased politicians to interest them in ocean racing. He raises funds for an international center for children through sailing events on the Volga River and on the enormous Rybinsk Reservoir. Enthusiasm for distance racing remains low in Russia, however. “Over the years, there were many times I didn’t even have enough money for the bus,” he lamented. To realize his dream, he had to break out of the mold established during Soviet-era cultural censorship. Two years ago, he started by corralling friends in earnest.

The orange-hulled The Grand is a tapestry of custom parts and friendly “sponsorship.” “I’ve won several races in Russia in the same kind of boat, but for this event, I added a new keel and rudder and rebuilt the entire interior. She sails closehauled very well. That’s why I chose the northern route,” he said.


Committing to the higher latitudes, though, meant he didn’t get much use out of the solar panel that powers his instruments. He only figured out how to work his new chart and weather software about half way across the Atlantic, but since his wind generator saw plenty of action, he was content.

One friend built the custom sails. Another friend, who works with medical electronics, bought the autopilot in Europe for half of what it would’ve cost in Russia.
Grinning, Igor told me that despite gales, whales, and dolphins, he ran with the autopilot about 80 percent of the time—with absolutely no failures or collision of any sort.

“Don’t get in the way of the boat. It knows,” is a Russian proverb that guides him. “If it got too windy, I’d just head to wind and go to sleep,” he said.
The Jester Challenge for singlehanded yachts—this was the third running—honors the achievements of two sailors aboard the Chinese junk-rigged Jester: Blondie Hasler and fellow singlehander Mike Richey, who owned the boat after Hasler. Jester finished second to Sir Francis Chichester’s Gipsy Moth II in the first singlehanded transatlantic race, held in 1960. The Challenge, as the organizers write, “fills a gap—satisfies a desire—and exists on the understanding that everyone has the right to sail across an ocean singlehanded and in company without submitting themselves to entrance fees (Corinthian money, better spent on the vessel) and rules, other than those governing common sense and good seamanship. There is no organizing committee; no one has a duty of care to the competitors other than the skippers to themselves, their dependants, and other seafarers.”


Clearly, with no onboard-communication requirements or check-ins, this is a different sort of race.

“In Russia, during most races, you can see each other, so I really had to click on my imagination,” says Igor. When he learned on Day 33 that he was ahead of the fleet, an eyebrow shot up, and his competitive streak spiked: yet another reason for him to smile and smoke some tea leaves.

Igor drove the last two days to his early morning first-place finish. Less than two hours later, Rory MacDougall completed the southerly route.
“I’m 40 this year, and I wanted to test my mojo again with the boat,” said Rory.


Rory’s been going steady with his self-built Wharram Tiki 21-foot cat since he and the boat met at the 1990 Miami Boat Show. “I was shaking the can for the American Cancer Society. I wanted to raise money for a good cause, and I was keen on a high-tech, sponsored attempt around the world in an open beach cat.”
He met two special people who made him change tack. “Meade Gougeon suggested I go out into the Gulf Stream in a norther, go to windward for a day, and then decide if I wanted to sail a 21-foot cat around the world.”

The second person he met was the Wharram rep, who introduced Rory to one of the company’s Polynesian-style cats. (Go to to see a review of the design, which was named Best Trailerable Gunkholer in CW’s 1982 Design Competition.) It was a build-it-yourself sailboat with some in-hull accommodations—”some” being the operable word here. “They made me realize there was a different possibility, not a hi-tech, busy, sponsor-driven attempt. Especially since I wasn’t getting anywhere, it became a low-tech, personal-driven odyssey.”

With and without crew, Rory and Cookie, as the boat is nicknamed, sailed and sailed for six years. In 1997, they entered the Guinness Book of World Records as the smallest boat to circumnavigate the globe.

Clearly, the relationship between man and boat hasn’t gone stale with age or miles at sea.

After I saw Cookie up close and personal, I concluded that the boat is cute, no doubt about it, but not roomy.

“No, you don’t build a 21-foot cat for roominess,” Rory concurred. “She’s built purely for the sea. You’re the one who adapts to a seaworthy boat.”

Still, the sea always finds ways to test a skipper and his ship. So on this trip, when the bow compartments and forepeak hatches leaked, he used extra foam tape and tinkered with the screws. Every few days, he hove to and pumped out the bows.

Speaking of the leaks, did I mention that Rory is justifiably obsessed with dry space aboard Cookie?

“I can face hell on Earth on deck as long as I know I have my little dry pit to go to,” he said. Aboard Cookie, he has a three-stage system to manage relative dampness. The wettest area is at the back, the middle splits the difference, and the dry zones forward are sacred for sleep and morale recharge. No damp drysuit is allowed.

On this crossing, each tack took about half an hour. To avoid spray, he heaves to and carries everything to the new windward hull.

“Harry the helmsman gets carried over. I also have to carry my daily equipment: my log book, my VHF, and my torches, sleeping bag, and toothbrush.”

A shortage of freshwater on board meant that Rory hauled in salt water for 20 days’ worth of potato meals and a mean cabbage concoction. When he needed to redistribute weight, he moved his 10 bottles of water; they weigh about 45 pounds. The fact that the boat is small makes such adjustments noticeably relevant to proper trim.

With a wife and two children home in Exmouth, England, he’s clipped in at sea 100 percent of the time. “I’ve had a lot of time to consider what it would be like to fall overboard and watch my boat sail away from me. I live in my harness,” he says.

While all his onboard tweaking sounds exhausting, he maintains that the hardest part of the Jester Challenge was getting to the start line.

“That’s the real challenge. We’ve got to organize our lives, make sure the postman doesn’t run off with the wife, make sure the bank doesn’t get the house, and that the kids don’t get taken by the social,” Rory said with a laugh.

In fact, he missed the skippers meeting—an inauspicious beginning.

All the skippers I spoke with emphasized that the motivation for the crossing was personal rather than competitive. Still, knotty situations will tickle the competitive bone.

When Rory’s wife told him on the satellite phone that he was neck and neck with Roger and with Igor on The Grand, he thought, “Don’t put that stress on me.” He knew that he’d entered the Jester Challenge to gain some publicity, attract people to his blog, _Cookie_’s Jester Challenge 2010 , and raise money for the Sir Francis Chichester Trust. That organization sends disadvantaged youths on Outward Bound-style courses to help their self-development through adventure. Having just moved back to the United Kingdom from Belize, he wanted to singlehand again and help a few disadvantaged kids enjoy adventures like he did, not worry about becoming becalmed or being ahead of other entrants.

The third Jester I happened upon in Newport was Roger Fitzgerald, a willowy 73-year-old production engineer who sailed around in nearly no wind at the start, waving good-bye to his grandchildren while onlookers shouted that he was going the wrong way.

In August 2006, Roger’s dream was triggered by an article about transatlantic sailing in Practical Boat Owner. With a thumbs-up from his wife, he had Ella Trout III, a Dehler 29, by September.

A lifelong dinghy sailor, he completed his first singlehanded race in the Jester Azores Challenge in 2008. He was ready for a bigger event, and with the Jester Challenge being the only transatlantic event this year, he threw his hat into the ring.

“It’s me gap year. I’ve worked all me life. I left school at 15 and started work at 15 and a half,” he said in his Yorkshire dialect.

From Day Two onward, Roger wrestled with a stowaway: a nasty respiratory virus. By Day 15, fraying strands in the wire rigging, at the lower termination on the port side, made him head south. “I had to give up my lead, and I basically nursed her home after that. If we hadn’t have had rig trouble, I’m sure we could’ve been in Newport three, four days earlier. She’s a beautiful sailer.”

Having overcome the virus and weathered the rigging woes, he felt especially badly when Ella Trout III, approaching the finish, ran aground on Brenton Reef. The only person there in the fog to help him out was photographer Billy Black.

“I set out a four-year plan, which I finished, with injury. It was a real bitter blow, that finish.” There are few perfect journeys, but despite it all, Roger arrived, bruised but safe, in third.

“I found the trip very hard,” Roger said.

In all, nine singlehanders would finish the challenge, following in the wake of such legendary solo sailors and dreamers as Chichester, Hasler, and Richey.
George Pike, a former organizer of the Bermuda One/Two and the OSTAR events, tracked the finishers. He pointed out that “about 3,500 people have climbed Mount Everest, but less than 500 have singlehandedly sailed the Atlantic.”

This year, 14 entrants retired from the Jester Challenge, many with a harrowing tale. Among them, Andy Lane’s 21-foot Amadeus was dismasted and sank. Lane was rescued by the motorvessel Courage, heading to Antwerp, Belgium. For a full list of entrants and results, visit the Jester Challenge site .

In Newport, Igor planned to sail home to his girlfriend and his land-lubbing cat of the four-legged kind. Rory, meantime, was spending time with his wife in Rhode Island and looking for a crewmate with a watertight tote bag to help get Cooking Fat back to England. And Roger—well, he was enjoying hanging around with his grandkids before shipping Ella back, his dream satisfied.

Trixie B. Wadson works as an independent publisher and freelance writer/photographer. She’s back home in Portsmouth, Rhode Island, after a year spent in Valencia, Spain.