San Juan Islands Sojourn

A family takes in the cedar trees, sea lions and fluky winds on a charter vacation in the Pacific Northwest.

September 3, 2021
San Juan Islands
The miles of shoreline throughout the San Juan Islands are fun to explore for kids and adults alike. Rob Roberts

Ticktocking the inboard from forward to reverse, Rob quickly pivoted the 43-foot Jeanneau in the 50-foot-wide fairway to avoid clipping an incoming cabin cruiser. I stood on the bow of Illumine with a fender, heart racing as we barely cleared the stern of a shiny Beneteau in its slip. I could practically high-five the couple loading groceries into its cockpit. As Rob and I anxiously called instructions to each other across the deck, I hoped that the stressful beginning to our charter in the San Juan Islands wouldn’t set the tone for the rest of the week.

Mike Houston, co-owner of San Juan Sailing in Bellingham, Washington, gave a relieved thumbs-up from the dock as Rob cleared the obstacles and turned Illumine into the channel to Bellingham Bay. I was grateful that Mike had politely insisted on giving us a 30-minute maneuvering lesson before we left. And I was even more grateful that Rob had drawn the short straw and agreed to be at the helm in the marina’s tight quarters.

Matia Island
Old-growth fir trees tower over 6-year-old Talon Roberts on Matia Island’s nature trails. Rob Roberts

“Well, that’s not the least stressful thing I’ve ever done,” my husband admitted. “Nothing like learning a new boat with a big audience.”


We both relaxed once we put the sails up. The wind was a perfect 15 knots, the late August sun glinting off frothy whitecaps. Illumine settled into a close reach like it was her favorite pair of slippers, slicing smoothly south at 8 knots. She was the most comfortable monohull we’d ever sailed, a beamy and well-cared-for delight above- and belowdecks.

Finn and Mark
Bellingham locals Finn Thompson and his dad, Mark, know all the good gunkholing spots in their backyard cruising grounds. Rob Roberts

Our son, Talon, one week into 6 years old, stood on the bow with me watching for porpoises, while his 2-year-old sister, Lyra, napped in one of the stern berths. “It looks just like sailing on Flathead Lake,” he noted.

He was right: We’d driven 10 hours from our home in western Montana to arrive in similar scenery. Douglas firs and yellow grasses adorned the mountainous islands, which were layered like turtlebacks atop the gray-blue sound. A seal’s whiskered nose broke the surface to starboard. “We definitely don’t have those in Montana,” I told Talon.

Cypress Island
The author and her kids check out a beach on Cypress Island. Rob Roberts

An archipelago in northwestern Washington state, the San Juan Islands lie in the rain shadow of Vancouver Island. This makes their climate drier and sunnier than the temperate rainforest in the Seattle area, making them a favorite Pacific Northwest cruising ground. A few years prior, our family had taken the ferry to the southern San Juans, where we camped on Lopez, Shaw and Orcas. We were excited to check out the more remote and undeveloped northern islands, which are accessible only by private boat. Chartering with San Juan Sailing out of Bellingham made the most sense—economically and geographically—for exploring these islands’ old-growth forests, fossil-filled cliffs and moss-lined hiking trails.

San Juan islands
Illumine, the Jeanneau 43 chartered from San Juan Sailing in Bellingham, Washington, was comfortable for the whole ­family and performed well in the fickle summer winds that flow through the San Juans. Rob Roberts

A few hours later, I was at the helm as we scouted anchoring options off Cypress Island. We dropped the hook in a deserted nook around the corner from Eagle Harbor, where two-dozen boats were already moored. Just after we secured a stern line around a tree onshore to keep us from pivoting with the notoriously strong tidal currents, our friends Mark and Katie and their 4-year-old son sailed into sight. Bellingham locals, they’d decided to buddy-boat with us for the weekend in their 25-foot Bayfield, Madrona. They nestled in enviously close to shore with a 3-foot shoal draft.

Rob lowered the 15-horsepower outboard onto Illumine’s ­dinghy so we could visit Cone Islands State Park, a quartet of tiny isles a few hundred yards away. One of our family’s favorite parts of cruising is joyriding around in the dinghy to explore. Katie and Mark, on the other hand, adore traveling without engines and opted for muscle power to row their wooden dinghy across to meet us.

baby crab
Tide-pool explorations in the San Juans reveals a treasure-trove of life, including baby crabs. Rob Roberts

The kids and dads poked at anemones in the tide pools while Katie and I basked in the sun like sea lions, happy to have the finger cove to ourselves.

“Should we skinny-dip?” I asked her, half-joking. But I should have known the answer: Katie and I had sailed together on a half-dozen sailboats in just as many countries, and she was always game for adventure.

“Heck yeah!” Katie said with a grin, shucking off her jeans and T-shirt. We splashed into the cold Pacific, our happy hoots bringing the children running.


The next morning, we set out for a hike on Cypress Island. Armed with copious snacks and a couple of field guides, we meandered through salal bushes and madrona trees, stepping over dozens of slugs as we climbed to the top of Eagle Cliff. The kids built rock cairns and ate peanut-butter sandwiches while the adults took in the sweeping views of Rosario Strait 750 feet below us. The white wakes of ferries and yachts looked like icing on a blue cake.

During a shared dinner of sausage ravioli that night in Illumine’s cockpit, we perused the charts with our friends. We decided to head for Clark Island—a 55-acre marine park with a long sandy beach—right after breakfast the next morning and crossed our fingers that one of the nine mooring buoys would be open if we arrived early.

We were in luck. After a two-hour sail in light winds (and only one terrifying moment when a freighter steaming at 14 knots turned toward us in the strait), Illumine and Madrona both picked up balls as two other boats were leaving. Talon and Lyra were so excited to see the new island that they climbed into the dinghy immediately, shoes in hand.

San Juan islands
llumine Rob Roberts

“Beaches make the best playgrounds,” Talon told us. “So hurry up, OK?”

The west side of Clark Island did not disappoint—its half-mile crescent of white sand felt like we were in California rather than a stone’s throw from Canada. The kids wrestled and rolled on the beach, built complicated castles, and chased garter snakes under driftwood piles. The adults cataloged the birds, took turns splashing into the water, and watched an otter eat several fish in the shallows. That evening, we headed back to the beach for a bonfire. The sunset painted the sea pink as we polished off our fire-roasted hot dogs and corn on the cob.

Madrona returned to Bellingham the next morning while we continued northwest. The wind was on our nose again (which Katie and Mark had informed us was the norm around Bellingham, no matter which direction you chose to sail). After two hours, Sucia Island’s Echo Bay came into view, a popular anchorage because of its splendid views of Mount Baker, the towering snow-covered volcano that dominates the skyline. I counted close to 70 boats packed into the U-shaped bay.

Put off by the crowds, we tucked around Matia Island instead. Back at the docks, Mike Houston had told us that it would be “highly unlikely” we’d be able to snag one of the two mooring buoys or few dock spaces in Matia’s Rolfe Cove, but to “definitely try because the island is spectacular.” Part of the San Juan Islands National Wildlife Refuge, Matia is home to one of the last intact old-growth forests in the San Juans.

We were thrilled to find both balls available—until we realized they were vacant because the swell coming into the cove was nauseating. The forecast showed the wind clocking south in the evening and calming considerably. So we hurriedly packed for a hike, fingers crossed that the boat would feel less like a roller coaster upon our return.

The 1-mile trail around the island felt like a fairy land. We wandered in awe through waist-high ferns, watching eagles and great blue herons dive into the green water beyond the forest. Sunlight filtered through the lacy needles of ancient cedars and dappled the kids’ blond hair.

“You have to do the limbo to look up at these trees,” our son said, arched over backward. He and his sister ran to a burn-scarred cedar, its trunk wider than a pickup, then stood together in the hollow V at its base. “Mom, we could practically live in here!”

Back on the boat, the swell had receded. I started dinner while Rob gave in to the kids’ pleas and took them back to shore to play with an inflatable beach ball. Their giggles echoed across the cove as they chased each other across the pebbled beach.

I let the chicken-and-rice dish simmer on the gimbaled stove, then took my beer to the cockpit to enjoy the sunset and rare solitude. Illumine was framed by sandstone cliffs on both sides, their hollows reflected on the smooth water. These rocks harbor fossils, and I searched for the feathery imprints of palm trees from a bygone era.

I was grateful that we were flexible on our charter, letting wind and whim dictate our destinations. If we’d planned out each stop, we might have missed the magic of Matia or the sand playground on Clark. While I reviewed charts and my charter packet before we arrived in the San Juans, I hadn’t read a single cruising guide. For me, the beauty of cruising is the constant discovery: catching a wind line just around the point; seeing the wake of a whale and chasing its spout; watching a seal slide through a bay at night, trailing phosphorescent fireworks. I prefer the giddy excitement of not knowing exactly what we might find, rather than following well-trodden routes to “must-see” destinations.

The next morning, we motored over to Sucia Island, our sails no match for the swirling tidal rip currents in light wind. We side-stepped the busy scene in Echo Bay and instead found a mooring in Snoring Bay, a skinny inlet on the south shore. We settled Illumine between a small sloop from Portland and a tiny wooden tug with a dog barking on the bow.

We hiked Sucia’s network of trails most of the day, finding sea stars and rock climbing along the way. Before dinner, we took the dinghy across the wide expanse of Echo Bay. We surprised a pair of enormous Steller sea lions as we zipped around the ­northwestern point. They bellowed angrily at the intrusion, ­hefting their intimidating bulk off the rocks. Motoring away quickly to calm them down, we noticed a rock spit a half-mile away with dozens more of the blond mammals. Talon was thrilled, demanding that we watch (from a safe distance) as two massive males fought over a harem of lady lions.

We didn’t leave Sucia until late afternoon the following day, eking out the last bit of sun and cedar from our vacation. San Juan Sailing had requested that we anchor close to Bellingham Bay on the last night so we could be back at the dock by 10 a.m. without risking navigating the soupy fog that often blankets Rosario Strait. We motorsailed toward Inati Bay on Lummi Island, which Mike Houston had recommended, “as long as you don’t mind the rigmarole of setting a stern tie.”

The sun had just slipped over the horizon as we pulled into Inati, a narrow hook into Lummi’s steep, verdant hillside. Four boats had already set anchor, three of them with stern ties. Only one slot was still open for anchoring—a little close to the rocks for my normal comfort level but plenty safe if we tied to shore. Rob and I set the anchor seamlessly, proud of our teamwork…but then promptly flubbed our success when Rob ejected his brand-new iPhone into the ocean as he stepped into the dinghy.

He stared incredulously down into the murky sea. The depth meter read 21 feet. The water temperature read 58 degrees. “I cannot believe I just did that,” he said.

I could tell he was itching to dive in after his phone, but with both kids bickering in the cockpit and Illumine swinging toward the rocks, I convinced him to set the stern line first. Once the boat was secured, Rob suited up in his spearfishing wetsuit in record time, happy he’d remembered to pack a dive light.

San Juan Islands map
San Juan Islands Map by Shannon Cain Tumino

While I whipped up some dinner, Talon narrated his dad’s progress: “He just went down again. I think that’s his 10th dive!”

But he didn’t need to tell me when Rob found the phone. My husband’s “woo-hoo!” echoed loudly off the walls, eliciting applause from folks on neighboring boats who were on deck enjoying the twilight. And the phone (in a waterproof case) still worked.

Rob grinned under his neoprene mask. “It wouldn’t be as memorable if the whole week went smoothly, right?”

After ramen noodles all around and bedtime stories for the kids, Rob and I sat back in the cockpit with a beer. We reflected on our week in the San Juans and both agreed: The minor mishaps made the highlights that much brighter.

Brianna Randall is a writer based in Missoula, Montana. She and her family explore mountain lakes on a Catalina 22 during the summer, and escape the winter to live aboard a shared Jaguar 36 in the Bahamas.

Clark Island
The long sandy beach on Clark Island frames an inviting ­anchorage. Rob Roberts

Chartering Information

When to Go: The weather in the San Juan Islands is generally mild year-round. The sailing season is from May to October, when the winds are mostly moderate, from 6 to 18 knots. Summer temperatures are ­typically in the low to mid 70s.

Cruising Guides: Before you go, consider taking a look at: San Juan Islands: A Boater’s Guidebook; 2nd edition, by Shawn Breeding and Heather Bansmer, and Waggoner Cruising Guide 2021 by Fine Edge Publishing.

Charter Companies: A number of charter options exist in the region for bareboat and crewed, power and sail.


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