Sail. Party. Repeat:  Whidbey Summer Classic Regatta is just around the corner

— Created July 19, 2023 by Kathy Reed

Photo Courtesy of Whidbey Summer Classic Regatta
There is still time to register to take part in the third annual Whidbey Summer Classic Regatta, taking place July 28-30 at the Oak Harbor Yacht Club. Local sailors are encouraged to participate. Registration is open until 5 p.m. Thursday, July 27.

By Kathy Reed

Sailing fans, take note! It is not too late to participate in the Whidbey Summer Classic Regatta.

The deadline to register is Thursday, July 27 and the third annual event will take place at the Oak Harbor Yacht Club July 28-30. Details and registration information can be found online at

Organizers said they are pleased to see an increase in registrations so far this year.

“This year has been great,” said Sail Fleet Captain Aaron Hale, with the Oak Harbor Yacht Club. “We have 10 boats from out of town registered so far and there’s still a week to go. We’ve really built it up this year and the community came together as well, providing 18 or 19 sponsorships.”

Over the past several months, Hale said he has traveled to yacht clubs all over the region to promote the regatta, including Orcas Island, Anacortes, Friday Harbor, Seattle and Everett. It’s a strategy that appears to be working.

“The most out of town registrations we’ve had in the past was two, and this year we already have 10, from Seattle and Bellingham and points in between,” he continued, adding he is still working to recruit more boaters. “I’m still in the trenches. I’m excited, but still focused on bringing in more people. The club is very excited with what they see as well, the growth.”

Hale, who has only been sailing for four years himself, said the idea for the Whidbey Summer Classic Regatta came about following the end of the longtime Race Week event for Oak Harbor a few years ago.

“We just wanted to try to keep something that carried on in that tradition,” he explained. “Being a hometown boy, I felt this was a great opportunity to highlight Penn Cove, the Oak Harbor Yacht Club, Oak Harbor and Coupeville. Bringing something to town to keep Oak Harbor thriving, that accents the water and what we are as a town, is what I like about it.”

Racing, of course, is the main attraction of the Whidbey Summer Classic. One doesn’t have to be an expert racer, because this event welcomes participants of all skill levels.

“We do have boats that are faster, with more experienced sailors, that race more competitively. We use the PHRS (Performance Handicap Racing Fleet) rating system for boats,” Hale said. “PHRS 1, that’s the great racers, nice boats. PHRF 2, that’s more for people just getting into racing and trying to become a part of it and learning how to race. We’re also trying to get some One Design boats in, where they can race each other with no handicap rating. We’ll be racing Friday, Saturday and Sunday, and we’re trying to get four races in a day for all the fleets.”

But the racing is only part of the fun planned for the weekend following a Thursday night check-in. There are plenty of things to do on shore as well.

“We’ll have field games going after the races for kids and some of us adults,” said Hale. “Friday night we’ll have a DJ playing music. Saturday night we’ll have a live band, the Soul Sirens. That’s kind of the premier night of the event. Sunday we’ll race, then come back and hand out trophies. There will be a lot of activities going on in addition to the races.”  

For those non-sailors in the community, Hale encourages people to come out and watch.

Photo Courtesy of Whidbey Summer Classic Regatta
Sailors of all skill levels from around the region will be taking part in the Whidbey Summer Classic Regatta at the Oak Harbor Yacht Club July 28-30. Organizers say registrations are up for this third annual event, but encourage anyone interested can register until July 27.

“It brings people out of the house, down to the beach,” he said. “As a community, we want to thrive, we want to see the history of what Penn Cove has been and keep that history alive. It’s one of the most important things to the community, even if people don’t get out on the water. It’s like a showcase.”

An alternative plan for those who want to watch, according to Hale, is to head to Coupeville between 1 and 3 p.m. July 28-30, find a restaurant with a good view of Penn Cove and watch the boats racing while dining.

Hale also encourages anyone who is interested in learning how to sail and race, to come down to the yacht club and check it out.

“Every Thursday we race with our club,” he said. “We invite the public to come down and get on a boat. People are able to race without it costing anything. If they like it, they can find a boat to race on or buy their own eventually. People who have never been on a boat come down and race with us.”

Local sailors are welcome and encouraged to participate. Look for more information and register online at

“There’s a lot of strategy behind racing a sailboat, but the biggest thing that draws people to it is the community of the sailors,” Hale said. “We all help each other out. It’s a fantastic community. We’re all in it together.”