When you dock a boat, everyone watches. My boyfriend, Tony, and I were closing in on an available space at a tiny dock on Stuart Island, a speck of land just under three square miles in size in Washington State’s San Juan Islands. We were aiming to parallel park in an empty spot next to one of the two small yachts already tied to the dock. As we maneuvered our bow and stern thrusters, we felt the eyes of other boat owners on us.
“Nice one!” said the septuagenarian owner of the neighboring yacht, just after Tony made the final maneuver that let me jump onto the dock and secure our lines. We were secretly congratulating ourselves, too, with an exchange of some knowing glances: We had just finished a two-day bareboat charter certification course with Anacortes Yacht Charters in these waters, followed by a five-day charter on our own if the instructor passed us. Luckily he did, and this was our first attempt at docking without the help of our instructor.
It’s been a lifelong dream of mine to learn to skipper my own boat. My father, who was born and raised in the Pacific Northwest, has plied the Salish Sea for much of his life as a first mate to his dad and then as a captain of his own boats. He introduced me to the region on a series of bareboat charters here during my childhood summers, when we’d return to see family between stints living in Hong Kong, Singapore, or wherever else his hotelier job would take us. I loved the uncharted nature of boating in the San Juan Islands, a collection of about 170 named islands—many more without official names (only four can be visited with a ferry from the mainland via the city of Anacortes). Most of these islands have no public transportation at all, and you need a private vessel to get there.
The interior of the Serendipity has wood trim, large windows, and a white ceiling.
Photo by Jennifer Flowers
The likes of Oprah have had homes here, but people don’t visit for luxury resorts; instead, the appeal of this place is its seclusion. Limited access to the more remote islands means that there’s a natural cap on visitation—the busiest months of July and August still feel blissfully off the radar here. (The San Juan Islands get about 650,000 visitors a year, and the lion’s share of them head to the largest islands of Orcas, San Juan, and Lopez.) But once you’re in on the secret, some folks like me become obsessed: I fell so hard for the San Juan Islands that close to a year ago, I moved to the archipelago’s largest, Orcas, which has its own little airport near my house. At about 6,000 residents, Orcas is one of the dozen or so islands here that are inhabited; some, like Sucia, have populations of as few as four people.
The San Juans are filled with secluded pebble beaches, enchanting old-growth forests, fascinating histories, and wildlife ranging from humpback whales and orcas to Dall’s porpoises. In the summers, the waters become bioluminescent. The bigger islands like Orcas have restaurants that punch well above their weight, including Matia, which has been recognized by the New York Times and nominated for a James Beard Award. To me, chartering a boat rewards travelers with a choose-your-own-adventure trip, where you can decide on a whim where you might go next, in a beautiful part of the United States that many Americans don’t know about.
How to explore the San Juan Islands by boat
You could spend weeks exploring the San Juan Islands and getting into the slower pace of life here. Our mode of transport was a 29-foot Ranger tugboat called the Serendipity—a sweet, chubby vessel that chugs along at a slow clip—a pace that’s perfect for leisure travelers. Our instructor, Mitchell, stayed with us for two days, and we took lessons out of Anacortes Marina. He taught us how to run our boat’s electrical systems and galley, navigate weather and some of the more hazardous rocky areas of the San Juans, and do crucial things like dock our boat—which he assured us that pretty much every captain still sweats over when they have an audience. I felt like an unconfident kid without her dad when I left the Anacortes Marina at the helm for the first time. But as we got underway in the Salish Sea, I was thrilled at my new boat skippering superpowers and excited for inexperienced adventures ahead. We’d head for smaller islands that are harder to reach, including Sucia, Patos, Matia, and Stuart.
After Mitchell let us loose, we headed for Stuart Island, which has no access points beyond a couple of small harbors and dirt runways for small aircraft. We left the narrow dock and entered the island’s mossy forest, with its winding paths along the shoreline and into the interior, and saw a deer wandering around—never too close, but walking near enough for us to keep an eye on each other. We returned to the boat to make dinner in our own galley kitchen with some of the supplies we picked up from the mainland—a hearty chicken curry followed by tea—staying cognizant of the draw on our battery, which only charged when we were underway or at a bigger marina with shore power. We loved feeling the cool and crisp air after sunset and played our favorite board game, Splendor Duel, before being rocked to sleep by benign waves.
Sucia Island (left) features madronas along the shoreline; Anacortes Marina (right) is lined with boats under a covered dock.
Photos by Jennifer Flowers
On another night, a few boating friends who live on Orcas Island caught up with us, and we moored together on buoys in a protected cove off of Sucia Island, about 20 nautical miles north of Anacortes. Yet again, Tony and I knew they were watching—and rooting for us, as we navigated a mooring buoy—a process that requires slowing down and snagging the chain of a floating buoy with a boat hook. We made it on the first attempt and celebrated over cocktails on a friend’s boat while watching red-footed pigeon guillemots dive-bomb into the water around us. The water was glassy that night, and the setting sun bathed its surface with a warm glow. Home was just a couple of miles away as the crow flies, but we felt worlds away.
On the last day of our trip, I invited my parents aboard for a spin. They took the 1.5-hour drive to Anacortes from their home in the city of Edmonds, and we picked them up and went to Watmough Bay, an idyllic little inlet on Lopez Island with high stone cliffs and emerald waters. Yet again, I had an audience—this time, my dad, my inspiration for this adventure. I was feeling pretty confident in my skills at that point, but he made me nervous—though it made my success at securing a mooring ball in front of him that much sweeter.
Later, I asked if dad wanted to take the helm for a while, and he obliged for a couple of hours, cruising the waters he knew like the back of his hand. After a while, he handed the wheel back to me. “I think you’ve got this, kiddo.”
Anacortes Yacht Charters offers bareboat charters for much of the year. While the company’s busiest months are July and August, the best time to charter can often be in the shoulder seasons in early September or late June, when the Salish Sea has fewer visitors—and more available places to moor your boat (and fewer people to watch you dock).
