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Feeding an old addiction in a new place

Stumptown, Bridgetown, Beervana, Rose City. Portland, Ore., has collected a slew of nicknames since it was put on the map in the mid-19th century. Some conservative pundits even called it “Little Beirut,” referring to protests against the policies of the Bush administration.

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Sounds like a place with potential. But what about “Sailingtown” or “City of Sail?” After 15 years of living under the California sun with the Pacific next door, scratching the sailing itch in my new hometown — 70 miles removed from big water and surrounded by more or less dormant volcanoes — was a big concern.

Portland’s name was decided by three coin tosses between Asa Lovejoy of Boston and Francis Pettygrove of Portland, Maine, two early settlers who wanted to name the new place after their respective hometowns. Its proximity to the deep waters of the Willamette and Columbia rivers soon brought ships, trade and commerce. A local hotel owner, Joseph “Bunco” Kelly, perfected the art of intoxicating and kidnapping young men to sell as deckhands to captains who were short on crew. Because shanghaiing was simple and profitable, it was an appealing business model in the city’s rough-and-tumble early days.

Today, Portland (population 560,000) is the third-largest city in the Pacific Northwest, behind Seattle and Vancouver, British Columbia. By U.S. standards, it is a surprisingly green and livable city with good schools, functional public transit and a vibrant bicycle culture. More than 30 microbreweries turn out fine suds, and indie java slingers make a mockery of Starbucks.

But what about sailing? Leave it to the kid to teach me.

During the summer, Olivia, my 8-year old, enrolled in her first Optimist class at the Willamette Sailing Club (, a local dinghy club with a floating clubhouse on the Willamette River, two miles south of downtown Portland. Lasers, Optis, 420s, Flying Juniors, Coronado 15s, Snipes, Vanguard 15s, Thistles, Lido 14s, and multiple copies of the venerable Tasar crowd the docks and the lot above the launch ramp. Perhaps I wouldn’t be stranded after all.

“Portland is greatly underrated,” says Chris Brown, one of the coaches at the club, a fifth-year senior at Oregon State University in Corvallis. “The sailing club is one of the city’s great secrets.” Brown also coaches the collegiate sailing team at OSU. “We have great local small-boat sailors, like Daryl Peck in the Finn or Bill Symes in the Laser,” he says.

But building a healthy base is the priority for Willamette Sailing Club president Michael Rees, a Portland lawyer. “Our focus is on sailing instruction, racing, and supporting high school programs,” he says. “We have 200 members and a large, active Laser fleet that puts 25 boats on the line at the Monday night races. But there’s no denying it: Sailing struggles to compete against other leisure activities.”

The club also runs the affiliated Willamette Sailing School that is staffed with US Sailing-certified instructors who teach approximately 60 classes for all skill levels. “We have more than 500 sailing students each summer — 200 kids and 300 adults,” says Janell Skeen, the club’s director of youth programs. “We recruit from the general public and also teach children of club members.”

Classes range from $50 to $180, which includes the use of a boat and a life jacket. To reach out to newcomers, the club holds open houses with free sailboat rides provided by club members and pirate parties with treasure hunts for kids. “Sailing has to overcome the elitist image that many associate with it,” Skeen says, “We show that it can be accessible and quite inexpensive.”

Judging by the numbers, attracting new people is not the problem. “The challenge is keeping them in the game,” says Kelly Heisel, a second-year instructor and a business major at Oregon State. She is an alumna of the Willamette youth sailing program and began to crew for her dad on a Lido 14 at age 6. “It’s not easy to stick with it if you don’t own a boat,” she says. “Students can take another class, but they can’t rent boats. However, crewing in the Wednesday-night double-handed regattas is an option.”

These races are hard-fought, as I have experienced firsthand. Light to moderate summer breezes blow mostly from the northwest and bounce back and forth between the steep shore and Ross Island. The courses are short, and the narrow river further compresses the fleet, so traffic is always dense. Success depends on boat-handling skills and anticipating the next shift.

Guessing what’s next in a small-boat market and a rocky economy is part of the job for George Yioulos, who grew up sailing on San Francisco Bay and graduated from the University of Oregon before buying West Coast Sailing, the local Vanguard dealership, three years ago ( “The 21st century mantra is ‘go fast and have fun,’ which calls for performance and recreational value,” he says.

Yioulos sells 25 models from five different brands, including rotomolded dinghies made by RS in the U.K. “Low maintenance is big because leisure time is scarce,” he says.

Building relationships and giving back to the sport as a sponsor are key strategies for Yioulos. “But to do that,” he says, “we need to grow outside the area.” Outside the area means Yioulos is making frequent trips to Cascade Locks on the Columbia River Gorge, 45 miles east of Portland, right on I-84. It is perhaps the best-known sailing venue of the area, a small-boat Mecca that attracts sailors from around the country and around the world.

The westerlies that blow here during the summer are squeezed and accelerated between the mountains, resulting in a fresh breeze that increases to 30 knots or more as they whistle upriver to Hood River, the Nirvana of boardsailors and kite boarders. “It’s the best heavy-air venue in the Northwest, a great place to develop skills in moderate-to-heavy air,” says Bill Symes, who grew up in Newport Beach, Calif., and now heads the Columbia Gorge Racing Association (, which operates from a beach at the Cascade Locks marina.

Symes, who took second in the Laser Master World Championships in 2002 and recorded three other top-five finishes, mentions Charlie and Jonathan McKee, Andy Mack, Morgan Larson, Mark Mendelblatt, and Courteney Becker-Day as sailors who have trained here and won Olympic medals and major championships. “The Gorge was always a windsurfing venue, but considered radical for dinghy sailing,” Symes remembers. “That changed about 20 years ago, when two locals, Kerry Poe and Chris Bittner, launched an Olympic campaign in the 470. They came here to practice, and others followed. But the sailing event that put the Gorge on the global map was the Nike Masters Games. Afterwards, Kerry and his wife, Amy, founded the CGRA.”

So far, more than 50 national and international championships have been sailed here in such classes as Optimist, Laser, Moth, Tasar, 505, and International 14, as well as small keelboats like the J/24 or Moore 24.

If anything is lagging, it’s the infrastructure, so Symes and his fellow members at the CGRA are raising funds for a world-class sailing center to accommodate regattas, clinics, high school and college programs, but also members of the public who can’t or won’t commit to boat ownership. “It’s the missing piece in more than one respect,” says Yioulos.

Lewis and Clark passed through this area in 1805, floating down the Columbia River on their canoes and staying for a few months a bit farther downriver, at Fort Clatsop. “At this place we had wintered and … have lived as well as we had any right to expect,” William Clark wrote in his journal, even though sailing was not on his mind.

So depending on my mood, I can go mellow on the Willamette or rough on the Gorge. And my daughter, who turned me on to sailing here by attending the classes at the club, already asked the all-important question: “When can we go sailing again?”

I worry no more. Portland, in its own way, is a City of Sail.

This article originally appeared in the December 2008 issue.