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Kevin Sherwood’s boat remained in dry dock as the Springfield, Virginia, sailor completed final repairs for the challenge that inspired him to buy the vessel: a 753-mile race from Annapolis to Bermuda.
Sherwood planned to launch the “Bay Retriever” on Wednesday before joining 20 other boats in the Annapolis to Bermuda Oceans Race. The competition was scheduled to begin at noon Friday with a trip south through the Chesapeake Bay and into the Atlantic Ocean.
The race, also known as A2B, dates to 1979 and ranks among the East Coast’s most demanding sailing events, Sherwood said. Four crew members will accompany him.
Sherwood bought the boat in 2022 specifically for the race, and every improvement since then has helped prepare it for the voyage.
Sailing in the relatively shallow, landlocked Chesapeake Bay is far different from confronting ocean waves and weather. Assistance is generally nearby on the bay, but boats racing toward an island more than 600 miles offshore will spend part of the journey beyond normal rescue range.
“We are on our own out there,” Sherwood said, noting that a passing freighter could be asked to assist during an emergency.
Because the Bay Retriever is smaller than vessels equipped with full galleys, its crew stocked up on food and water at a grocery store. Team members will alternate between sailing and resting below deck.
A lee cloth, similar to a hammock, will keep a sleeping sailor from falling when the boat heels to one side.
From dead calm to 15-foot waves
Sherwood has competed in the race twice before, experiencing dramatically different conditions.
During his first trip, calm winds left his team barely moving at two knots for two days. Two years ago, clouds obscured much of the sky as waves reached 12 to 15 feet.
Clouds, fog and rain have limited the sunsets on recent voyages, he said. But under a clear, star-filled sky, the isolation can be extraordinary.
Starlink provides some contact with the outside world, although crew members are generally either concentrating on their duties or resting.
Sherwood acknowledged that some moments will leave him questioning why he entered. Still, he values the teamwork and the trust required when sailors hand control of the boat to crewmates at the end of a watch.
Arrival time depends on the wind
Weather will determine how long the race takes. Sherwood said exceptional conditions could put the crew in Bermuda by Tuesday. Great conditions could mean a Wednesday arrival, average weather could push it to Thursday, and terrible conditions could delay them until Friday.
People at home will be able to track the boats online. Dockworkers in Bermuda are expected to greet arriving sailors with a Dark ’n Stormy, one of the island’s national drinks.
Sherwood hopes to earn another podium finish and bring home a trophy, but his priorities begin with safety.
Completing 753 miles of ocean sailing is itself a source of pride, he said. His first goal is to return home safely in about two and a half weeks, followed by reaching Bermuda safely and then securing a strong finish.