Temptation/Oakcliff captures 2025 Annapolis-to-Newport Race line honors

Temptation/Oakcliff captures line honors for 2025 Annapolis-to-Newport Race © Willy Keyworth

Arthur Santry competed in the Annapolis to Newport Race many times aboard his father's boat named Temptation. The Arlington, Virginia resident has done the iconic distance race several times aboard his own series of boats also named Temptation.

Santry and Temptation had never been an Annapolis to Newport winner until now. Santry skippered Temptation/Oakcliff to an impressive performance in the 40th biennial Annapolis to Newport Race. Not only did the Judel/Vrolijk 66-footer capture line honors as first to finish but is likely to earn the overall victory on corrected time as well.

Temptation/Oakcliff crossed the finish line at Castle Hill Lighthouse just before 1 a.m. Tuesday morning to post an elapsed time of 61 hours, 10 minutes and 40 seconds. Yellowbrick Tracking has the JV66 winning ORC 1 class and ORC overall on corrected time.

"It feels great and I give credit to the crew for sailing the boat so well," said Santry, who was back in his office at Cushman & Wakefield in D.C. by Tuesday afternoon. "Everyone did a really good job and the boat performed wonderfully." Santry's best previous finish in the Annapolis to Newport Race came in 2015 when he sailed Temptation (Ker 50) to third place in IRC 1 class.

Dream Crusher, a Kernan 47 skippered Devin McGranahan, was winning ORC 1 upon completion of the Chesapeake Bay portion of the race, which is 120 nautical miles. Temptation/Oakcliff crossed the Chesapeake Bay Bridge Tunnel around 10 a.m. on Sunday, meaning it took almost 22 hours to get out of the bay.

"We were sailing in 2 half knots of wind for a couple hours in the Chesapeake Bay," tactician Gary Jobson said. "It was a very slow trip."

Upon rounding the Chesapeake Light Tower, which is 13 miles offshore in the Atlantic Ocean, the Temptation/Oakcliff braintrust elected to head further offshore. They wound up going 20 miles east of the rhumb line and at one point were 80 miles east of New York City.

"We made one really bold decision and that was the difference. We knew the wind was going to come from the east so it made sense to head that way," Jobson said. "We had a discussion onboard and just felt like it would work and it did. We had really good boat speed for most of the time we were out in the Atlantic Ocean."

Temptation/Oakcliff captures line honors for 2025 Annapolis-to-Newport Race - photo © Willy Keyworth

Jobson said Temptation/Oakcliff reeled off considerable mileage while sailing in winds ranging from 25 to 27 knots. Crew members had the sail and rig tune dialed in and the 66-footer was consistently posting 12 knots of speed for lengthy periods of time. It was an upwind beat for the entire Atlantic Ocean portion of the race.

"When you're going close-hulled for 300 miles in 12 to 20 knots of breeze, this boat is very tough to beat," Santry said. "Having the wind on the nose for the ocean leg was hugely beneficial for this boat. That's a big differentiator, without question."

Meanwhile, all the boats that sailed a rhumb line course or one just west of the rhumb line never saw that type of wind velocity. Santry said the Yellowbrick tracker showed Temptation/Oakcliff adding eight miles to its lead over Dream Crusher in the span of an hour.

"We legged out pretty good on the rest of the fleet," said Santry, adding that Temptation/Oakcliff sailed on starboard tack almost the whole time it was offshore.

Temptation/Oakcliff did suffer a slight setback upon approach to Block Island as the headstay broke and the crew was unable to hoist a jib. Jobson said the boat raced the final 28 miles with a staysail and mainsail, possibly adding as much as two hours to the trip.

Jobson said the afterguard had planned to go outside of Block Island, but the broken headstay forced them to go inside instead. Santry said it took three hours to cover the final 10 miles, a task made more difficult by a strong current coming out of the Narragansett River.

Santry has a long-term charter agreement with Oakcliff Sailing and campaigns the JV 66 in various ocean races and major regattas. He does so with a crew consisting partly of students participating in Oakcliff's high-performance racing program.

For this race, the crew included six Oakcliff trainees ranging in age from 17 to 24. Many other members of the 18-member crew, including navigator Hugh Dougherty, are graduates of Oakcliff programs.

"It's a really fun boat to sail and I love having the Oakcliff students aboard," Santry said. "I've been lucky to have a lot of these young people grow and graduate then remain part of the program for years going forward."

Not all of the younger sailors aboard were Oakcliff students as Santry also had his nephew Peter Santry, neighbor Will McMahon and Hobart/William Smith sailor Thomas Walker.

Santry mixed in some old salts such as Jobson, winning tactician for skipper Ted Turner aboard Courageous in the 1997 America's Cup. Jobson — a renowned author, lecturer and television commentator — is a member of the National Sailing Hall of Fame and arguably the sport's greatest ambassador.

"I've known Gary since 1976 when we were part of the same America's Cup syndicate," said Santry, who crewed aboard Independence for the defender trials. "Gary is just a phenomenal sailor and the ideal watch captain. His strength is how well he handles everyone on the boat."

Also aboard as watch captain and strategist was another longtime friend of Santry in Mark Myers, Past Commodore of Annapolis Yacht Club who skippered his J/44 Tonic in the Annapolis-to-Newport Race many times.

Two weeks ago, Temptation/Oakcliff was the overall winner of the Block Island Race on both elapsed and corrected time. Santry is hopeful of duplicating that performance in A2N to jump-start a busy schedule that includes the New York Yacht Club Annual Regatta this weekend, the Around the Island Race and Marblehead-to-Halifax Race.