2015 Cape Charles Cup (

Fair Winds

The Leo Wardrup Cup is a cruising event for serious racers, and vice versa

The Leo Wardrup Cup is a cruising event for serious racers, and vice versa

Each August, dozens of sailboats dot the southern Chesapeake Bay, gathering for a weekend of competition and camaraderie during the Leo Wardrup Memorial Cape Charles Cup.

The regatta returns for its 16th year this Aug. 9-11, sending cruisers and racers from Norfolk to Cape Charles, on Virginia’s Eastern Shore, and back during the destination race by Broad Bay Sailing Association.

“People absolutely love this race,” said Christina Ritger who, with her husband, Ben, is co-chairing the 2019 event. “It’s a cruising event for serious racers and the racing event for serious cruisers. There’s literally room for everybody in the regatta.”

The idea for a race across the southern Bay was born more than a decade ago in a conversation between friends.

“I was new to racing, and I was dissatisfied with the length of the races and wanted more opportunities,” said Bill Barnes, one of the Cup’s co-founders and a longtime participant in the regatta. “A few of my close friends who were veteran sailors—Leo Wardrup and Sonny Smith—gave us the idea of a two-day race to Cape Charles and back.”

Wardrup, a retired Navy captain and longtime Virginia House delegate, agreed to raise funds for the new regatta if Barnes organized the event. With the help of Lou Tuttobene, John McCarthy, and Scott Almond, the duo drew more than a dozen sailboats the inaugural year, and the Cape Charles Cup was born.

The casual competition quickly grew into one of Broad Bay Sailing Association’s most popular events, according to Scott Almond, a lead racing official for the event. He watched the Cape Charles Cup draw more than 70 cruisers and racers by the third annual event.

“I would attribute it to Bill and Leo’s event philosophy,” Almond said. The two-day race was “unlike any other event in our area,” providing a weekend-long slate of sailing and social events that quickly became the talk of crews in the southern Chesapeake Bay. “It helped that Leo and Bill had found a decent amount of sponsors, because the race was well-funded, the trophies were nice and the parties were great.”

After Wardrup passed away in 2014, organizers renamed the race in his memory. His 38-foot schooner, the Black Widow, still races in the Cup each year.

“It wouldn’t have happened without Leo,” Barnes said.

“Leo Wardrup was the force behind the event,” said Hank Giffin, former race chair and still an organizer behind the event.

Fundraising allows the organizers to keep entry fees low—$115 ($165, if received after July16). The fee gains participants a package including a regatta T-shirt, hat, and other gifts, as well as meals and drinks, starting with Friday night’s dinner in Norfolk and including four tickets to the renowned dinner and after party Saturday night in Cape Charles. Every skipper gets a copy of the regatta yearbook, which features the participating boats and skippers.

“All told, the package is worth between $350 and $400,” Giffin said. “We consider it the best bargain in the Bay. We raise money in order to keep the race entry fees low and keep the things that really keep the race fun.”

Even so, the regatta’s growing popularity has allowed sponsorship dollars to surpass the cost of hosting the event, leading to a partnership with Sail Nauticus. The Norfolk-based non-profit sends youth on the water to learn about science and develop life skills from swimming and first aid to teamwork, leadership and communication through sailing.

“Leo developed that relationship back in 2012. We all knew at that point that Sail Nauticus was a good program that helped kids get involved sailing,” Almond said. “That was where we wanted to be—helping programs that educated kids through sailing.”

“They do an amazing community outreach and we believe that you can learn things on the water that you couldn’t learn anywhere else,” Ritger said.

As Barnes sees it, Sail Nauticus can bring new life into local sailing, too.

“We need young people coming in, and hopefully some young people in Norfolk will have the sailing experience and be interested in moving up into bigger boats,” he said.

Crowds will gather in the hundreds for the 2019 Cape Charles Cup, kicking off Friday night, August 9, with a skipper’s meeting complete with dinner, drinks, and music at Bay Point Marina in Norfolk.

On Saturday, rolling starts of various classes launch from Norfolk’s Little Creek Marina and crews race roughly 16 miles across the Chesapeake Bay to Cape Charles.

The slower boats start first to allow the fleet to sail in similar conditions and arrive together for the party. The winners of the classes are determined by handicapped corrected time to make the racing as fair as possible.

“It really opens up the playing field and that’s what I think is so alluring,” Ritger said.

Saturday night, an awards ceremony and after party takes place on the C-Pier at the Oyster Farm Marina, in Cape Charles, where crews are greeted with cold drinks, buffet dinner, and live music. Top competitors in each class take home a one-foot-tall crystal sailboat by Virginia Beach’s own Glass Baron Art mounted on a varnished wooden base, “The most beautiful piece of crystal you’ve ever wanted,” Giffin said.

Crews launch from Cape Charles the following morning and race back to the western shore, marking the end of the Cup, and the start of planning for next year’s event.

“It’s a year-round process. It doesn’t stop. Once the race is over, you start planning for the next year,” Barnes said.

From ordering trophies to coordinating with the U.S. Coast Guard, the Cape Charles Cup “takes a lot of effort to coordinate,” Giffin said—but the event is worth organizers’ efforts.

“Everybody just seems to get along [in] the different generations. Saturday night when the band starts playing, you get people in their teens and in the 80s out there dancing,” Giffin said

“It’s what sailing is all about in my eyes. It’s the perfect opportunity to enjoy your boat, find a few friends, enjoy food, enjoy a couple of beverages, and just be yourself. And it’s working… They keep coming,” he said.

“If you have a sailboat and you know how to sail, then come on, join us,” Ritger said.