Skip to main content
Like many Northwest kids, my sons have grown up on skis and snowboards. But I grew up back East, where my sister, brother, and I moved into our teenage years with wooden planks under our bare, deeply tanned feet. We cruised around the Eastern seaboard on our father’s 54-foot classic wooden sailboat. My brother loved the lifestyle so much that, instead of college, he worked as a deckhand on yachts in the Caribbean, later became a captain, and now lives in Antigua. My sister left college to cook on a charter yacht out of St. Thomas.
I followed suit and became a yachtie, too. For seven years and thousands of nautical miles throughout the Caribbean and Mediterranean and around Tahiti, I lived the life depicted in the reality show Below Deck.
I kept the interior of a hundred-foot yacht spotless and served meals and drinks. Many, many drinks—including once, memorably, to Mick Jagger.
I thought that part of my life was behind me once I moved to Portland. I’ve always known the Columbia River is a windsurfing mecca, but that didn’t appeal to me as much. Wind- and kitesurfing and wing foiling involve one person on one board, while sailing is best enjoyed in groups. Trimming the sails and changing the boat’s direction requires teamwork and communication, and that camaraderie is what I like most about being on the water. And I’ll be honest, sailing is not so physically demanding as solo water sports. You rarely fall into the water, and you certainly don’t need a wetsuit.
But what makes the Columbia world class for windsurfing makes it fantastic for sailing as well. It’s all about the wind. The warm air of the Eastern Oregon desert pulls cooler air from the mouth of the Columbia inland, creating a steady wind that gets stronger as you head east. It whips through the Gorge Canyon into Hood River where it’s strongest, making that an ideal spot for windsurfers, kitesurfers, and wing foilers who need forceful gusts.
Sailboats require much less wind because the sails are larger, with more area to catch the wind and move the vessel. This means winds can move more slowly and you’ll still get a smooth ride.
What sailing lacks in an adrenaline rush, it makes up for in relaxation. There’s nothing like setting the sails in place and settling into the echo of the breeze and the lapping of waves against the hull. Especially with a cold drink.
The biggest barrier to sailing is the boat. Investing in a sailboat is a much, much spendier proposition than coming up with windsurfing gear (best bet: Find or make a friend with a sailboat!). But there are plenty of options along the Columbia where sailing newbies and salty dogs can catch the sailing bug, whether it’s an adventure for an afternoon or a lifetime.
Island Sailing
515 NE Tomahawk Island Drive, Slip D-85, Portland, 503-285-7765, islandsailing.org.
Its motto is: “It’s time to turn the motor off.” Membership at this Hayden Island sailing club includes access to its fleet of boats, making sailing more affordable than boat ownership. It offers beginner to advanced classes on ballasted keelboats from 22 to 31 feet and a bareboat chartering course.
Passion Yachts
260 NE Tomahawk Island Drive, Portland, 503-289-6306, passion-yachts.com.
A boating program called SailTime Portland offers an economical way to learn to sail and get on the water. You get beginner to advanced classes on sailboats from 22 to 46 feet and reserved boat time to practice your skills.
Portland Sailing Center
3335 NE Marine Drive, Portland, 503-281-6529,
Independently owned and proud of it, Portland Sailing Center offers beginner to advanced courses on ballasted keelboats from 22 to 39 feet. Students have access to affordable boat rental packages. Located near Portland International Airport, with easy access to the Columbia, the center promises to get you flying across the water in no time.
Hood River Yacht Club
2149 Cascade Ave., Suite 106A, Hood River, 412-965-3729, hryc.clubexpress.com.
HRYC calls itself “a friendly group of sailors and boaters.” This club helps sponsor a junior program and adult learn-to-sail classes as well as Wednesday night races. In July and August, the club hosts open sailing nights. Open to the public. All ages welcome. Instructors, junior instructors, and experienced sailors are available to answer questions and take people sailing. Fun-filled family event with lots of boats on the water, even SUPs and kayaks. No registration needed. Just show up with your life jacket.
Looking to watch a sailboat race from shore?
The Hood River Yacht Club’s “Double Damned” Sailboat Race takes place Aug. 10 and travels from Cascade Locks to The Dalles. regattanetwork.com/event/27670
Racing the Columbia
sailpdx.org, syscosailing.org.
For veteran racers, both SailPDX and SYSCOSailing put teams together, coordinate regattas, and need sailors in the warmer months.
Columbia Gorge Racing Association
Marine Park, 355 Wa Na Pa St., Cascade Locks, cgra.org.
This nonprofit conducts regional, national, and international regattas. It also hosts community sailing nights and a barbecue on Thursday nights in the summer. Novice sailors can hop on boats to get the full racing experience. Located on the stretch between Stevenson, Wash., and Cascade Locks, it’s an ideal section of the Columbia, with consistent, moderate wind for racing small boats.
This story is part of Oregon Summer Magazine, Willamette Week’s annual guide to the summer months, this year focused along the Columbia River. It is free and can be found all over Portland beginning Monday, July 1st, 2024. Find a copy at one of the locations noted on this map before they all get picked up! Read more from Oregon Summer magazine online here.
