40th biennial Annapolis-to-Newport Race - Day 2
by Annapolis Yacht Club 8 Jun 18:20 UTC
June 6, 2025
Boats in ORC 2 sailing upwind in close quarters shortly after starting the Annapolis-to-Newport Race © Willy Keyworth
An hour before the Saturday start of the 40th biennial Annapolis-to-Newport Race, a massive storm front swept over Annapolis. It steadily grew darker and more ominous as boats motored towards the starting area for the mandatory check-in with the Race Committee.
Suddenly the skies opened and torrential rain came down sending sailors scurrying down below to avoid getting soaked to the bone. However, Mother Nature must be a sailboat racing fan because the rain squall blew through toward the Eastern Shore after about a half hour and the skies steadily cleared and the sun peaked through.
The Annapolis Yacht Club Race Committee postponed the start for 40 minutes to allow for a southeasterly sea breeze to fill in, then sent the 34 boats in three classes down the Bay.
ORC 1, featuring the largest, fastest boats in the entire race, started first on Saturday with Velocity, a Class 40 skippered by Annapolis Yacht Club member Marty Roesch coming off the line with speed and taking an early lead. However, it did not take long for Temptation/Oakcliff, a Judel/vrolijk 66-footer, to overtake Velocity and begin to leg out on the fleet.
Temptation/Oakcliff, skippered by Arthur Santry, is the scratch boat in the 2025 Annapolis-to-Newport Race and the favorite to capture line honors as first to finish. It is part of the Oakcliff Sailing program inventory of boats.
Santry has a long-term charter agreement with Oakcliff 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.
Also aboard for the Annapolis-to-Newport Race is Gary Jobson, a member of the National Sailing Hall of Fame and winning tactician for skipper Ted Turner aboard Courageous in the 1977 America's Cup. Jobson, a renowned author, lecturer and television commentator, is arguably sailing's greatest ambassador.
Jobson jokingly described his role aboard Temptation/Oakcliff as "watch captain, tactician and psychologist." He enjoys sailing with the six Oakcliff students that range in age from 17 to 24.
"They're all very good sailors, energetic and eager to learn," said Jobson, who was a member of the New York Maritime sailing team when he competed in the 1969 Annapolis-to-Newport. "It brings back good memories because I was their age the first time I did this race."
Jobson is the current Rear Commodore of the Annapolis Yacht Club. He was joined as a watch captain aboard Temptation/Oakcliff by Mark Myers, a Past Commodore and close friend of Santry, Executive Vice Chairman of Cushman & Wakefield.
Two weeks ago, Temptation/Oakcliff was the overall winner of the Block Island Race on both elapsed and corrected time. Santry is hopeful the team can duplicate that feat in A2N.
"I think we're confident we'll cross the finish line first. The big question is can we win after the handicaps are computed because we owe a lot of time to these other boats," Jobson said.
Jobson isn't the only Annapolis Yacht Club flag officer participating in this year's Annapolis-to-Newport Race. Commodore Chris Bell is crewing aboard Reindeer, the Morris 47 skippered by Tony Parker.
Newbold Smith first sailed a boat named Reindeer in the 1959 edition of the Annapolis-to-Newport Rae and became the Class D winner in 1961 and 1963. The Philadelphia resident was a devoted fan of the biennial event and rarely missed a race.
Parker initially crewed for Smith in the 1981 Annapolis-to-Newport when Reindeer was a Concordia-built Farr 44. That was one five different designs Smith owned with the last being a Morris 47. After Smith died in 2019, Parker bought the boat and continued the tradition of Reindeer racing in A2N.
"When I became Commodore I vowed to compete in the Annapolis to Newport Race this year, which is one of our signature events," Bell said. "It is truly an honor for me to race aboard a legendary boat like Reindeer."
This is the sixth time Bell has crewed aboard an entry in the Annapolis to Newport Race, which is intertwined with the history of AYC.
"It is an iconic and enduring race with an incredible history and tradition," Bell said. "Sailboat racing is the heart and soul of this lub, and this is our signature offshore event. It is very, very important to our membership."
Reindeer wasn't the only renowned raceboat competing in ORC 2 class. Running Tide, a Sparkman & Stephens 61 with a distinct black hull and beautiful lines, is doing the Annapolis-to-Newport Race for the eighth time.
Northern Virginia real estate developer Al Van Metre skippered Running Tide in every edition of A2N from 1973 to 1983, capturing line honors that final year. Beau Van Metre reacquired Running Tide and spent $4.5 million restoring the old warhorse so it could compete in the 2021 edition of the Annapolis-to-Newport Race.
Saturday's starters were hopeful of exiting the Chesapeake Bay by early Sunday morning in order to latch into downwind conditions that would provide a spinnaker run up the Atlantic Coast. However, the forecast called for light winds for most of the 120-nautical voyage from Annapolis to the Chesapeake Bay Bridge Tunnel.
"It shapes up to be a classic Chesapeake Bay drifter early on. Hopefully, the breeze picks up somewhere along the line or otherwise it's going to be a long trip to Newport," said Erik Wulff, skipper of the Farr 400 Endorphin that is competing in ORC 1.
Wulff recently retired as a Washington, D.C. attorney and is competing in Annapolis to Newport for the first time. He is among many skippers that will do the New York Yacht Club Annual Regatta this weekend then head to Block Island Race Week the following weekend.
"My primary goal is to get there safely. I just hope we sail the boat well and if that happens we should be in contention within our class," Wulff said. "Our challenge is to keep pace with the faster boats such as the JV 66 and Kernan 47. If we can keep them in our sight, we'll be in good shape based on rating."
Annapolis Yacht Club member Ken Comerford skippered Dark Storm to victory in ORC 2 class in the 2023 edition of the Annapolis-to-Newport Race and is hoping to repeat. Comerford, owner of North Point Yacht Sales, had sons Kyle and Willy aboard as watch captains.
Dark Storm, a J/121, is the shortest and lightest of 14 entries in ORC 2 — an advantage in light air, but not as much in strong winds. Running Tide is the scratch boat in the class and quickly took a comfortable lead shortly after the start. Comerford sees Reindeer as a contender because it performs well going upwind and the XP 44 Phantom due to its speed in reaching conditions.
"To be totally honest, we're not really concerned about the competition. We're just looking to sail our own race," Comerford said. "We've got a good boat and a strong crew, so if we sail to our potential we should do well. Our goal is to get out of the bay first in our class [on corrected time]. If we can achieve that, it will set us up well for the remaining two-thirds of the race."
Also starting Saturday were the 14 boats in ORC 3, which included a regular A2N participant the J/120 Windborn. Richard Born will be skippering the boat for the third time in Annapolis to Newport after previously crewing for his father.
Born believes the best strategy in the Atlantic Ocean will be to hug the coast and sail as close to a rhumb line course as possible.