Harken Derm

Oakcliff Sailing: Lean in and take it on

Published on May 29th, 2019

It’s hard to imagine all the moving parts at Oakcliff Sailing in Oyster Bay, NY. Founded in 2010 by Hunt and Betsy Lawrence in order to raise the caliber of sailing in the United States, there is not much the organization is afraid of trying, and for most of everything they lean in and take it on.

This report comes from Oakcliff Sailing Executive Director Dawn Riley:


After blitzkrieging through the Melges 24 Distance Race earlier this month, the Oakcliff team went straight into a full regatta schedule that included a Grade 4 and 5 Match Race events and the Block Island Race which began May 24 from Stamford Harbor (CT), taking the fleet through Long Island Sound on the 186nm course around Block Island.

Despite weeks of hard work weighing on the staff, they pulled together with Supporters and Saplings for their best finishes ever in the Block Island Race. Oakcliff Farr 40 Blue won their division and was awarded the Governor’s East Race Trophy for best elapsed time in a PHRF fleet. Farr 40 Black rounded out the podium with a third place finish. Farr 40 Red finished close behind in fifth place.

However, the crew of the Ker 50 Temptation-Oakcliff led by Art Santry stole the show with a first place finish in IRC4, which included heavy hitters like the Ker 40+ Christopher Dragon, the R/P 45 Pterodactyl, and the Santa Cruz 52 Magic.

Not only did they score a win but their corrected time was just five minutes faster than Pterodactyl who was followed two minutes later by Magic. The crew of Temptation was awarded the Commodore’s Trophy for winning the division with the tightest finishes.

“Preparation was everything and it really paid off,” said Temptation Boat Captain Brian Reilly. “We had a full sail inventory that included a jib top and a staysail which were key for a fast, balanced reach to Block Island.”

After exiting Long Island Sound through the Race, the breeze died around 3 am. “Just three miles from the first turning mark off Block Island, we dropped anchor until the breeze turned back on an hour later. I think that was the move that gave us those five extra minutes to win the race,” said Oakcliff Fleet Manager and former Temptation Boat Captain Greg Adams.

When the breeze filled in, it came from the north so Temptation raised their spinnaker and ran to the mark. Rounding the island, they switched to the J1. On their way back towards Long Island, they saw a rare sight: a whale broaching at sunrise less than a boat length away (see video).

“It was so close it felt like you could reach out and touch it,” said Brian. For many of the crew it was the closest they’d ever been to a whale. The light wind gave them the opportunity to enjoy the sight of the beautiful creature.

Temptation returned to Long Island Sound through Plum Gut with the current in their favor. Navigator Suzy Leech and the crew had a lot of local knowledge which really helped them play the eddies; they were able to get a full knot of additional current boost at times.

However, the crew suffered a blow to their morale when they hit another spell of glassy water and watched Pterodactyl disappear beyond the horizon. Art did a really good job keeping the crew motivated. He broke out what remained of the 45 sandwiches they had and adamantly reassured the crew that a southerly would fill in in the next 15 minutes.

Sure enough, fifteen minutes later, they were sailing along at 9-10 knots toward the finish in a building southerly.

It was full upwind mode with active trim on the main and the jib. The crew got a second wind when they saw Pterodactyl’s sail appear on the horizon; they were reeling them in. They pushed hard right to the very end. They had no idea they had beat Pterodactyl on corrected time until an hour later when they were on their way back across the Sound to Oyster Bay.

“The theme for the boat this year was the old and the new working together,” said Brian. “I’m the new Boat Captain and I was sailing with Greg, the old Boat Captain. We had a lot of older, more experienced crew with really valuable local knowledge but we also had new, young sailors on board who were sharp and eager to learn.”

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