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The boat that Kevin Sherwood of Springfield, Virginia, bought is still in dry dock as he makes final repairs and preparations ahead of the whole reason he bought the “Bay Retriever” in the first place.

If all goes as planned, he’ll get it in the water Wednesday, and starting at noon on Friday, he’ll be heading south down the Chesapeake Bay on a 753-mile voyage to Bermuda.

Sherwood’s boat is one of 21 in this year’s Annapolis to Bermuda Oceans Race, or A2B, which dates back to 1979. He’ll be joined by a crew of four others in a race he said is among the most challenging on the East Coast.

“I bought this boat in 2022 specifically for the Bermuda race,” Sherwood said. “Since I bought this, everything we’ve done has been prepping for it.

“Plenty of sailors never leave the Chesapeake. It’s very different when we’re dealing with ocean waves, ocean weather, all kinds of different conditions. So, the boat really needs to be set up for it.”

The bay, being both relatively shallow and surrounded by land, can make for ideal sailing; if something still goes wrong, help isn’t far away.

Heading out in the blue waters of the Atlantic Ocean to an island more than 600 miles off the coast can present more difficult circumstances. Yet, if you go on the race’s website, you’ll see a long list of people hoping to get picked up by a boat to help take part.

“We’re out of rescue range for a portion of the trip. They’ll ask a passing freighter to come help you if you have a problem,” Sherwood said. “We are on our own out there.”

Some boats will have full galleys available to help cook meals for the crew. But Sherwood’s vessel, being smaller, has been stocking up on food and water from the grocery store.

He and the crew will take turns sailing and resting in the cabin down below. A “leak loss” — imagine a hammock, more or less — will catch anyone if the boat leans one way while they’re sleeping, lest they fall to the floor.

Of course, that assumes they’ll have strong winds and waves. Sherwood, who has done this race twice before, said that’s not always the case.

“My first Bermuda race, we had plenty of nothing going on,” he said. For two days, the winds were so calm Sherwood’s team was “barely making two knots.”

Two years ago, he saw more clouds than stars and sun, and waves were running 12-15 feet high.

“The last couple of races we haven’t seen many sunsets because of clouds, fog, rain, that sort of thing,” Sherwood said. “But when you are out there all alone and just the stars, it’s incredibly detached. There’s really nowhere left in the country to get this isolated.”

Of course, having access to Starlink means there is some connection out on the water — though, if you’re on duty, you’re too focused to care. If you’re not, you’re probably resting.

“There’s definitely parts I’m going to hate,” he said. “There’s parts I’m going to be asking myself, ‘Why am I doing this? Why am I here?’ But it’s just such an awesome team sport. When I go off watch, I’m trusting the other guys to keep sailing, keep racing, to keep us safe, to keep the boat moving fast. We get to detach from the world.”

WTOP/John Domen

WTOP/John Domen

For how long is anyone’s guess. Weather and winds will determine the time it takes to get there.

“If conditions are amazing, we’ll get in on Tuesday,” he said. “If conditions are great, Wednesday. If they’re average, Thursday, and if they’re terrible, Friday.”

Those following from home can track Sherwood and everyone else in the race online. Whenever he arrives, he said workers on the docks will have a “Dark n’ Stormy” — one of Bermuda’s national drinks — waiting for them.

He’ll also be hoping to be handed a trophy he can sail back with, but that’s not the most important thing right now.

“There’s a point of pride just for completing this; 753 miles of ocean sailing is a big deal,” he said.

“So, yeah, I mean, I want to do well, but my first goal is just to make it back here safely in two and a half weeks. My next goal is to make it to Bermuda safely. Then my third goal is to finish well and get a podium finish again.”

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