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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The Virginia Lottery offers multiple draw games for those aiming to win big.

A bus driver with a history of speeding accusations was indicted on additional charges Monday in a chain-reaction crash in Virginia that killed five people and injured dozens more.

Jing Sheng Dong, 48, of Staten Island, New York, initially was charged with two counts of involuntary manslaughter after the crash early Friday morning on Interstate 95. On Monday, a grand jury indicted him on three additional charges of involuntary manslaughter and one count of reckless driving, according to a statement from the Stafford County Commonwealth’s Attorney’s Office.

Authorities said Dong was driving a motorcoach from New York to North Carolina when he struck a line of vehicles that had slowed down in a work zone. A family of four from Greenfield, Massachusetts, on their way to a wedding were killed, as was a 25-year-old woman from Worcester, Massachusetts.

Dong, who remained hospitalized Monday, previously was accused of speeding in Colonial Heights, Virginia, in November 2024 and in Annapolis, Maryland, in March, according to online court records. In the latter case, he is accused of driving a motorcoach 72 mph (116 kph) in a 50 mph (80 kph) zone.

In the Virginia case, Dong was convicted of driving 73 mph (117 kph) in a 55 mph (89 kph) zone and paid $219 in fines and court costs. He also has a pending case in Mecklenburg County, Virginia, where he was accused of trespassing in July.

The bus involved in Friday’s crash was operated by E&P Travel Inc., based in Kings Mountain, North Carolina. The National Transportation Safety Board is investigating the crash, a board member said.

Court documents related to the bus crash do not list an attorney for Dong. Neither the attorney representing him in the trespassing case nor the lawyer representing him in Maryland responded to emails seeking comment Monday.

Prosecutor Eric Olsen said Dong will be transported to jail upon his release from the hospital.

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Ramer reported from Concord, New Hampshire.