A gentle puff filled our sails, and we scooted ahead with a couple of golden knots of boat speed. Nice. Then we hit a velocity header and began our current-swept reverse track back in the direction of Buckeye Shoal off the northwest tip of Cypress Island. Sometimes that’s sailing, isn’t it?

We were just a couple of hours into the 2024 48° North Cruising Rally, but we were moving south, back to Anacortes. Huh? Oh right, we were cruising; why not just turn on the engine?

And that’s where we were really out of luck. We had a line inexorably wrapped around the propeller and were mired in our Rosario Strait yo-yo of no progress toward the port that was both the day’s starting point and suddenly its inevitable destination. With a trickle of water coming in at the prop shaft and many hours before the breeze might build in earnest, the writing was on the wall. We were going to need a tow.

After the 2023 edition of the 48° North Cruising Rally in the San Juan and Gulf islands, I wrote a “pinch me” article, hinting that we spent the week waiting for the other shoe to drop because it was so dang good. It never did on that glorious trip. Cue the 2024 “dropped shoe edition” of the rally. Only a few hours into this year’s event, three of the 11 boats that began were down, not to return, all with engine-related problems.

By the end of the week, an additional array of challenges—boat-related and not—left me and our rally group reflecting ambivalently. And that, to me, was the big lesson from the 2024 rally: If you cruise long enough, things can and will go wrong, sometimes dancing dangerously near the edge of disaster; and yet, it is still unquestionably worth venturing out.

Though glossy magazine articles and hyper-produced YouTube videos might suggest otherwise, real boaters know that things don’t always go right when you’re cruising. Often you can pinpoint the cause, like with nasty weather, an acute boat handling mistake, or an overambitious plan. But other times, it just feels like what it genuinely is—a bit of bad luck. The night before the rally, I stood in the produce section of the grocery store in Anacortes, staring at the bananas. I thought to myself, “I know the rule, but I really want some bananas. And I don’t believe that old superstition anyway.” Idiot.

When we hauled out at our rally headquarters to address the now-leaking prop shaft, we discovered bent engine mounts (damn, Dyneema line is strong!) and began working out a Plan B to continue the rally without the boat that was supposed to be leading it. I found myself thrust back into the land of nautical superstition, feeling somewhat to blame for the bad luck on the rally’s first day. I threw the bunch of bananas away at the boatyard, and you won’t find any of those yellow luck-busters on my boat from here on out, I promise.

Still, the group that was able to carry on, myself included on a different boat, had an absolutely marvelous trip. We were predictably, yet still speechlessly, wowed by the natural beauty of the San Juan and Gulf islands. We were won over by the generosity, support, and camaraderie of our fellow rallygoers. And I was strengthened in my conviction that the way we handle adversity is the most important factor in an adventure ultimately being rewarding or regrettable.

What’s The Rally All About?

Founded in 2018, 48° North’s Cruising Rally is an idea that developed out of collaboration between me and Ullman Sails loft owner Chuck Skewes, and we’ve always run it in partnership. At its core, it’s a community connection event for us and some of the people who love both 48° North and PNW cruising.

More tangibly, it’s an exercise in the “safety in numbers” value of group cruising and a chance for folks whose skills and confidence run the gamut to travel together, learn from one another, and share a bunch of great experiences.

A few other rally priorities have floated to the top over the years. One is a focus on anchoring out in harbors and coves that aren’t always the hottest spots. We like to avoid crowds when possible. We make a concerted effort to help rally participants try things that have a slightly increased degree of difficulty, like rafting up or doing a stern-tie anchoring setup, sometimes in combination.

Additionally, we’ve found that our participants find the nudge to cross the border into British Columbia valuable. Many longtime cruisers might think that unremarkable, but for newer cruisers, that international boundary and the unknowns about customs protocols mean they stay stateside for many years before making the jump.

In the end, this rally ticked all those boxes. I’m proud of this event, especially of the community it continues to build. And on a personal note, it helps get me out cruising, too, which stokes the fire of my passion for that activity, especially when I share it with a terrific group of rallygoers like this year.

The 2024 Trip

As in previous years, our 2024 rally began and ended in Anacortes. We had eyes on a big travel day on our first day out, hoping to clear customs and head into the Gulf Islands right away. However, our preferred anchorage for that night (an old rally favorite, Medicine Beach, at the north end of Bedwell Harbour) is not the place to be with any amount of southerly breeze. Wouldn’t you know it, the forecast for day one was an unstable and potentially building southeasterly.

Prudence led us to lay up in the always-wonderful Prevost Harbor on Stuart Island, just a 4-mile hop to the customs dock in Bedwell the next morning. Those who didn’t experience the unfortunate delays of engine failures and boatyard haulouts enjoyed cooperative currents and awesome sailing when transiting the northern edge of the islands. A run trending to a reach with breeze in the mid-teens—it doesn’t get much better. By the time I caught up with them at Stuart, every boat there was floored by the great day, even as they hunkered down in the evening’s intermittent downpours that splashed wildly down on the placid waters of the protected bay. Though going ashore at Stuart Island offers excellent walks, the rain kept most folks aboard in their dry cabins instead of taking dinghies in for short hikes or the long stroll out to the Turn Point Lighthouse.

I caught up with the group thanks to the generosity of four-time rally participant and good friend Ed. He recently sold his Tartan 3400 and is trying out his first powerboat, an elegant Tiara 30. Ed generously towed in the poor rally headquarters boat and allowed me to stow away for a few days. We zipped through the islands averaging a little more than 20 knots on his powerful new ride to catch up with the group.

When we pulled into Prevost in the early evening, rally friends Ralph and Kicki waved us in to raft up to their J/120. They were on cloud nine after a chilly but exhilarating day of sailing, and saw the weight of the day’s stresses and uncertainty on my face. They immediately invited Ed and me in for dinner, and we accepted. Soon, the clouds over my first rally day had been burned away by the warm hospitality and friendship of my fellow ralliers.

Day two would transition us from cold and wet back to weather befitting the summer season, but not before some careful and/or delayed travel thanks to pea soup fog. We pulled anchor and made for the Bedwell Harbour customs dock on British Columbia’s South Pender Island. Even a boat like Ed’s Tiara, which can do nearly 30 knots, slows to cruising sailboat speeds when wading through such low visibility.

The group rapidly cleared into Canada with zero excitement (just how we like it), and we made our slow turn north into Swanson Channel, carefully avoiding the vessel no-go zone to protect whale habitat along the southwest shore of North Pender Island. I’d like to say that we were keeping our eyes peeled for orcas, but we were mainly straining our eyes in the fog and attentively alternating between the radar screen and our buddy boats.

Our day two destination was Princess Cove on Wallace Island, and as we headed north, the fog cleared and another sailable southerly filled in. It turned into a genuinely lovely day of travel, and sailing amongst the Gulf Islands is always such a special experience.

Knowing that the island and anchorage are favorites of so many, we have wanted to put Princess Cove on the rally itinerary for many years, but it wasn’t until this year that I decided we should go for it. It’s the farthest north our rally has ventured, and considering its popularity and limited space, we’d always wondered if we’d ever find room for our fleet. We made it happen in 2024, but it wasn’t exactly easy. It was, however, very worth it!

Princess Cove is a breathtakingly beautiful narrow inlet with about 15 stern-tie rings on the west shore. So bringing our fleet, even now reduced from 11 to eight, presented a challenge. But that wasn’t the only hurdle. Pulling into the cove, we discovered a catamaran that arrived before us had dropped anchor and was set up to swing, blocking at least four stern-tie rings. Adding to the excitement was the southerly wind, which by this time had built to 15 knots out in the channel, and some portion of that was trickling into our little cove as a cross breeze. Stern-tie anchoring is one of my favorite ways to spend the night, but getting set in that orientation with wind on the beam is kind of a drag. Speaking of dragging, thankfully the breeze never built enough to make anyone’s anchor drag, which cruising guides note can be a risk here. When the breeze finally decreased in the evening, it was most welcome.

Catamaran aside, one of the interesting discoveries at Princess Cove was that there is enough room for a few boats to swing on slightly short scope on the east side of the inlet while still allowing others to stern-tie. No doubt it’s snug, but it is possible, and good to know for future visits.

This was my first time on Wallace Island and boy, did it meet expectations. Several friends have declared it their favorite island, and I can see why. The narrow island is overflowing with amazing views, superior hiking, and oodles of gnarled madronas. In the two primary anchorages, Princess and Conover coves, the shallow, protected waters warm (slightly) in the summer sun, and there were a number of swimmers in each location. Aside from two remaining private properties, it’s all B.C. Provincial Marine Park and is wonderfully idyllic—it’s not surprising that it was once home to a summer camp and a resort.

Anticipating all of this Wallace wonder, we enjoyed our planned layover day at Princess Cove. The camaraderie of our rally group really took shape there, as it always does. Group gatherings and activities facilitate this, and between the blissful get-together on Ed’s boat on our first night in Princess Cove, some fun group hikes ashore, goofing around with the sail rig on Ed’s ship-to-shore tender, and a dinghy dock happy hour on our second night, we were suddenly a group of fast friends. It’s part of the group cruising magic that I’ve come to expect from each rally. To top it off, we were treated to an epic, seemingly never-ending sunset on our last night at Wallace.

For the final night of our rally, we headed to a stopover that almost always makes its way onto our rally itinerary, Saturna Island’s Winter Cove. The well-protected cove has piles of room, great anchoring in just-deep-enough water, and views galore to the Vancouver metro through Boat Pass and of the sunset over Minx Reef.

Like Wallace, there’s a fabulous B.C. provincial park to visit ashore in Winter Cove, with a very short but rewarding hike to see the tidal flow (and the occasional ambitious powerboat) rushing through Boat Pass.

By the time our rally crew pulled into Winter Cove after another great day of making miles under sail, which I shared with my friend Peter and his pup Buddy on his Saga 35, individual itineraries and a few participants down with illness meant that our group was even a few boats smaller. But we still had a splendid walk out to Boat Pass together, and were treated to another breathtaking sunset. It was a quiet but ideal way to wrap up the rally experience.

With a long final travel day ahead, we waved our goodbyes to our new friends and to the Canadian cruising grounds in the soft light of early morning. In spite of its challenges, it was another great 48° North Rally, and it was my privilege to share this experience of cruising beauty with a fleet of such good-hearted, hospitable, and fun rallygoers.

Parting Thoughts

For any cruiser, there’s a lot of buildup, anticipation, and expectation when we head away from our home ports for destinations known or yet to be explored. You might think that the longer the cruise, the more that’s true. However, I’d suggest that perhaps the opposite is the case. For those with time-consuming responsibilities ashore, sometimes that cruise is the single opportunity for a year’s lot of waterborne wonder. It’s sort of similar to the way you seldom hear ski bums complain about the conditions, but instead it’s the family who dropped major dough in hopes of an awesome experience that day who will be most disappointed by less-than-stellar snow. The 48° North Rally is, in its own way, our one annual shot at this version of cruising bliss, and it brings ample expectation for our participants and for me. It’s also an encouragement to myself and others to just cruise more often.

Of course, that may not be realistic for many of us. When you don’t or can’t cruise often and things don’t go right, especially at the start, there’s a painful sting in the loss of the perfect experience. There’s no way around that bummer. But finding your way through it, continuing on, and giving yourself the opportunity to have your cup filled by the amazing goodness of even a less-than-ideal cruising experience—that’s the spirit of adventure. And that’s already making me excited for next year’s cruising rally.

Joe Cline is the Managing Editor of 48° North. He’s presently on paternity leave to spend time with his infant son, and is enjoying learning about being a father of two.