Mastering Boat Skippering in Washington State’s San Juan Islands

As we approached a small dock on Stuart Island, a tiny piece of land spanning just under three square miles in Washington State’s San Juan Islands, all eyes were on us. My boyfriend, Tony, and I were preparing to parallel park next to one of the two yachts already moored. With the help of our bow and stern thrusters, we maneuvered into position while feeling the gaze of other boat owners upon us.

“Well done!” exclaimed the elderly owner of the neighboring yacht, just after Tony executed the final adjustment that allowed me to leap onto the dock and secure our lines. We exchanged a few proud glances, secretly congratulating ourselves: we had just completed a two-day bareboat charter certification course with Anacortes Yacht Charters in these waters, followed by a five-day charter on our own—provided our instructor deemed us ready. Thankfully, he did, making this our inaugural docking attempt without his assistance.

For as long as I can remember, it’s been my dream to learn how to skipper my own boat. My father, who grew up in the Pacific Northwest, has navigated the Salish Sea for most of his life, first as a first mate to his father and later as the captain of his own vessels. During my childhood summers, he introduced me to this beautiful region through various bareboat charters while we visited family, navigating between stints in places like Hong Kong and Singapore, where his hotelier job took us. I was captivated by the wild, untamed beauty of boating in the San Juan Islands, which consist of around 170 named islands and countless more without official titles (only four can be accessed via ferry from Anacortes on the mainland). Most of these islands lack public transport, requiring a private boat for exploration.

While celebrities like Oprah have residences here, visitors aren't drawn by lavish resorts; rather, it's the solitude that captivates. The limited access to the more secluded islands naturally restricts the number of visitors—July and August, the peak months, still feel wonderfully untouched. (The San Juan Islands attract around 650,000 visitors annually, with most heading to the larger islands of Orcas, San Juan, and Lopez.) Once you discover this hidden gem, you might become as enchanted as I did: nearly a year ago, I relocated to the largest island, Orcas, which has its own small airport near my home. With around 6,000 residents, Orcas is one of the inhabited islands; some, like Sucia, boast populations as small as four.

The San Juans are a treasure trove of secluded pebble beaches, captivating old-growth forests, rich histories, and diverse wildlife, including humpback whales, orcas, and Dall’s porpoises. In summer, the waters glow with bioluminescence. Larger islands like Orcas host surprisingly excellent restaurants, such as Matia, which has received acclaim from the New York Times and has been nominated for a James Beard Award. For me, chartering a boat offers travelers a unique choose-your-own-adventure experience, allowing spontaneous exploration in a stunning part of the United States that many are unaware of.

Exploring the San Juan Islands by boat

You could easily spend weeks discovering the San Juan Islands and immersing yourself in the relaxed lifestyle here. Our transportation was a charming 29-foot Ranger tugboat named Serendipity—a delightful, stout vessel that glides along at a leisurely pace, ideal for leisurely exploration. Our instructor, Mitchell, joined us for two days as we learned from Anacortes Marina. He guided us through operating the boat's electrical systems and galley, navigating weather conditions, and maneuvering through the rocky hazards of the San Juans. He also taught us the essentials of docking, reassuring us that even seasoned captains get nervous when there's an audience. Leaving Anacortes Marina at the helm for the first time felt daunting, like a child without her father. However, as we set sail into the Salish Sea, I was thrilled by my newfound boat-skipping abilities and eager for the adventures to come, heading towards the less accessible islands like Sucia, Patos, Matia, and Stuart.

Once Mitchell set us free, we made our way to Stuart Island, which can only be reached via a few small harbors and dirt runways for small aircraft. After departing from the narrow dock, we ventured into the island's lush, mossy forest, exploring winding trails along the shoreline and deeper into the woods, where we spotted a deer—never too close, but near enough that we could keep an eye on each other. Afterward, we returned to our boat to prepare dinner in our galley kitchen, whipping up a hearty chicken curry followed by tea, all while being mindful of our battery consumption, which only charged when we were underway or at larger marinas with shore power. We enjoyed the cool, crisp air post-sunset and played our favorite board game, Splendor Duel, before the gentle waves lulled us to sleep.

On a different evening, a few boating friends from Orcas Island joined us, and we anchored together on buoys in a sheltered cove off Sucia Island, approximately 20 nautical miles north of Anacortes. Once again, Tony and I were aware of their watchful eyes and encouragement as we approached a mooring buoy—a task that requires slowing down and snagging the buoy's chain with a boat hook. We succeeded on our first attempt and celebrated with cocktails on a friend's boat, watching red-footed pigeon guillemots dive into the water around us. That night, the water was like glass, and the setting sun cast a warm glow on its surface. Although home was just a couple of miles away as the crow flies, we felt a world apart.

On the final day of our adventure, I invited my parents on board for a spin. They made the 1.5-hour drive from Edmonds to Anacortes, where we picked them up and headed to Watmough Bay—an enchanting inlet on Lopez Island with towering stone cliffs and emerald waters. Once again, I had an audience—this time, my dad, who inspired this journey. By then, I was feeling fairly confident in my skills, but his presence made me a bit nervous; however, successfully securing a mooring ball in front of him felt all the more rewarding.

Later, I asked my dad if he’d like to take the helm for a bit, and he happily agreed, steering the waters he knew intimately for a couple of hours. After some time, he returned the wheel to me, saying, “I think you’ve got this, kiddo.”

Anacortes Yacht Charters provides bareboat charters throughout most of the year. Although July and August are the peak months for the company, the ideal time to charter often falls in the shoulder seasons of early September or late June, when the Salish Sea sees fewer visitors and offers more available mooring spots (along with fewer onlookers while you dock).