Chasing Chichester, 50 Years Later

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.