Two novice sailors, one 24-foot sailboat, and 10 days of making friends, navigating swells, and enjoying the Pacific Northwest.

Amuse Bouche, our 1976 C&C 24-foot sailboat, was the only vessel locking through the Hiram M. Chittenden locks into Puget Sound that first morning. It made for a comfortable start, as we chatted—a little too eagerly for 6 o’clock in the morning—with the lock attendants about our upcoming adventure to the San Juan Islands. They suggested a few of their favorite spots and as the water level dropped, our excitement rose. The lock gate opened and we made that wonderful right turn, heading north and leaving Seattle’s noise, congestion, and safety behind. With a gentle breeze at our backs we set our sails wing-on-wing, shut off our noisy eight-horsepower two-stroke outboard, and made our first run for the famous San Juan Islands!

A year earlier, we were browsing Craigslist on a Friday afternoon when we came across a sailboat listing. It seemed like a good deal—she was only 24-feet long but had everything we would need to enjoy some amazing weekends cruising the Puget Sound: a comfortable V-berth to sleep on, a little salon in the cabin to hide from the rain, as well as a camp stove, freshwater tank and sink, portable toilet, good batteries, and even a 7½-foot dinghy.

We’d been living in Seattle for a few years at this point and had fallen absolutely in love with the natural beauty of the region, but without a boat we knew we were missing out on half of what this place had to offer. After a short husband-wife conference perusing the listing, we made a deal a couple of hours later. For a few thousand dollars, we bought ourselves a terrifying (yet exciting) new hobby.

As Kenneth Grahame once said, “There is nothing — absolutely nothing — half so much worth doing as simply messing about in boats.”

Jen and Dan Legg at Friday Harbor

Sailing Lessons for the First Long Trip

After a year of messing about, we took her on our first long sailing trip to the San Juan Islands. It doesn’t sound like much, but to novice sailors like ourselves, you might as well be talking about crossing the Pacific Ocean. (We know, people have crossed the Pacific Ocean in boats much smaller than ours. But they had to start somewhere too, right?)

Aside from learning general sailing skills, cruising meant we needed to learn anchoring methods and etiquette, how to read charts, use a VHF radio, raft up to other boats, provision the boat, and troubleshoot an engine. Not to mention, we needed to know how to account for wind, current, and tides when planning a passage. No individual skill is overly complicated (though many of the forum discussions on anchor choice would have you believe otherwise), but it definitely felt a little overwhelming when we considered everything at once. But we’d already booked the time off work! So we left.

Mother Nature’s Change of Plans

On a Sailboat

After a full day of downwind sailing, we made it up the east side of Whidbey Island, dropped anchor near Coupeville in Penn Cove, and felt quite pleased with ourselves. The one improvement we’d made to our boat in the last year was the addition of a 25-pound anchor with 100-feet of chain. It was to make sure we wouldn’t drag, especially as we slept (a painful lesson learned during the previous year).

Setting anchor, we took our dinghy to the Front Street Grill — a waterfront restaurant and pub. We were in search of hearty sustenance to ready ourselves for the big transit through the notorious Deception Pass and Rosario Strait towards the San Juan Islands. Front Street didn’t disappoint. We’d come for the famous Penn Cove mussels, to which an entire section of their menu was dedicated.

Unfortunately, the next day’s planned sail wasn’t meant to be. The temperature dropped, the rain started, and the wind picked up throughout the next morning as we motored up towards Deception Pass. Amuse Bouche doesn’t have an enclosed cockpit, which means the helmsman is always exposed to the elements. While we’d brought “waterproof” clothes, they were our hiking rain jackets — that useless combination of waterproof and breathable that is actually neither. 

After a few hours, we tucked into a marina near Deception Pass to dry off, warm up, and check the weather before trying to catch the next slack tide through the pass. It was a good thing we did. The weather report had changed — the strait was seeing gale force winds, six-foot seas, and a small craft advisory had been sent out. So, we found a protected anchorage off Hope Island and hunkered down for the next two days. Luckily, the delay wasn’t without its advantages. Crab season had just started, so we dropped our pot and filled our bellies with fresh Dungeness crab.


Braving the Crossing with Nerves of Steel

The wind slowed, and the small craft advisory was lifted. We waited for slack tide with the other sailboats and then pushed on through Deception Pass. Our boat only does 4 knots with the engine going and we had been warned by nearly everyone that currents in Deception Pass run as high as 7 knots. Timing was critical. So were steely nerves.

Despite feeling comfortable with the wind and sea state predictions for crossing the Rosario Strait, we did not factor in the giant wakes left behind by the luxury yachts as they screamed past us. We did our best to take the waves on the bow and avoid the uncomfortable side-to-side rolling, but the tiller still popped out of the water and sails luffed as the waves crashed over the bow and we continued to lose speed and steerage.

All the while, we gripped the tiller with white knuckles, waving to the power boaters and trying to prevent our little sailboat from being overpowered by the tide rips. We assured ourselves (aka lied) that the boat felt totally normal and we were entirely in control.

Eventually, though, the traffic eased. We found ourselves on our own in the gentle swell with the wind on our beam as we slowly made our way across the largest body of water we’d ever seen from our little boat.

Savoring the Views of Our Labor

sailboat at a dock

Having crossed through the Lopez Pass, we arrived in the protected lake-still waters of the San Juan Islands. Our anxiety about the crossing waned as we were greeted by seals, bald eagles, and porpoises in the Lopez Sound. In Spencer Spit State Park, we set anchor and enjoyed a breathtaking sunset from our deck. There was some solace to be had in the fact we were enjoying the very same view as those luxury yachts anchored next to us, the same ones that nearly swamped us coming through Deception Pass. We deserved it.

The next couple of days were spent cruising around Lopez, Shaw, and Orcas Islands, enjoying the calm waters, incredible homes, and breathtaking scenery. Because our sailboat only goes a few knots-per-hour, we took a shot at trolling for salmon and even caught a Chinook!

Yet even with our fresh catch, we needed to restock provisions. The Orcas Village Store, located near the beginning of West Sound, was the perfect place. Utilizing the public dock, we were able to pop-in and score everything from fresh veggies and specialty items to fuel and ice. Plus, the staff was super friendly and made us feel right at home.

Eventually, we made our way to the famous Friday Harbor on San Juan Island for the Fourth of July celebrations. There we made friends, as we like to do. They even invited us to raft up next to them in the busy marina after they noticed us having trouble finding a place.

We spent the rest of the day enjoying Friday Harbor’s shops and restaurants. Among our favorite bites were the fish and chips at The Bait Shop, where newspaper lined baskets came loaded with fries and delicately battered fish. The evening’s Fourth of July festivities also didn’t disappoint. We were treated to some great live music and a beautiful fireworks show just a few hundred feet away from our dock. It was an unforgettable experience that we definitely hope to make into a tradition.


The trip wasn’t without its rookie mistakes though — we had a dock line fall into the water and fouled the propeller not once, but twice. Both times it left us drifting towards some very nice yachts with no fenders prepared or the ability to steer. (Luckily, neither time ended in a collision.) On another occasion, we ran out of gas while in a marina and found ourselves pushing our sailboat into a safe location while we scrambled to add fuel from an auxiliary tank.

Aside from learning that we need to be more aware of lines in the water and not to trust our fuel gauge, we also learned the boating community is one of the most helpful and welcoming we’ve ever been a part of. With each of these mishaps, we found a group of heroes rushing to help out and get us safely ashore, always with a friendly “been there before” or “still more graceful than what I did there yesterday.”

Despite the significant differences in the values of our boats, we learned that everyone is just happy to be out there on the water, enjoying quality time with their friends and families in some spectacular natural surroundings. This may have been our first big sail, but it certainly won’t be our last. Who knows, we might even sail around the world one day. 

More San Juan Islands Tips


If you’re San Juan bound, don’t miss your chance to snap a selfie by these epic lookouts, historic sites, and cute creatures!


247 average days with sunshine, a reputation for wholesome fun, and more than 6 places to get freshly made pastries all make Friday Harbor is the ultimate kid-friendly getaway destination that the whole family will love.


With the sun on your face and two wheels at your command, San Juan Island is yours to explore – as fast or as slow as one of Susie’s Mopeds will take you.


Windswept grasslands and breathtaking views make the southernmost tip of San Juan Island the perfect location for a day hike.