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Many people believe that the happiest days for a boat owner are the day they buy their boat and the day they sell it. While this may hold true for some, it’s not quite my experience.
Recently, I found myself reflecting on the essence of boat ownership. After three wonderful years and over 3,000 nautical miles, I had to bid farewell to Journeyman—the Cal 40 that served as the teaching platform for my sailing school, Griffin Bay Adventures, located in the enchanting San Juan Islands.
Journeyman’s commercial insurance was up for renewal, and despite extensive searching, I found no coverage for the 50-year-old vessel, despite her impressive pedigree. Like any craft shared over countless miles, Journeyman held a special place in my heart. However, as a business asset, she had become a financial burden during difficult times for the sail training industry.
While preparing to sell her, I meticulously listed the upgrades we had made, and reviewing the photos brought a flood of cherished memories of adventures shared aboard. I fondly recalled the 21 days it took to sail her back from Hawaii, amazed that the tales I’d read about her ocean sailing capabilities were indeed true. I remember our success in the Oregon Offshore Race, where we secured a second-place trophy, proudly trained with students in our sail training class. Additionally, I cherished the memory of a race around San Juan County with friends where, despite our less-than-stellar placement, we feasted on a gourmet meal prepared with cast-iron cookware. I also think back to New Year’s last year when we sailed to Vancouver, British Columbia, and the blissful days spent cruising around the Gulf Islands with a girlfriend, our bellies filled with oysters, tucked into a favorite newly discovered anchorage.
As boat owners, we are merely stewards for a time, and it’s important to remember that our vessels allow others to share in the joy they bring. If we care for our boats as we wish to be cared for ourselves, we should aim to pass them along in even better condition than when we received them, enabling future generations to enjoy them.
I initially glimpsed Journeyman while prepping a Santa Cruz 50 for delivery back to San Francisco. Although she had undergone a recent refit, she was in poor condition after being mishandled by her previous owners during her journey to Hawaii. Her stem fitting and gooseneck were broken, and her jib and furler were so damaged they were discarded. Despite her rough state, I saw great potential in her as a reliable sail-training platform, and her classic lines drew me in. With a bit of work, she would be ready for the 2,500-plus mile voyage home.
It’s the misadventures, as much as the smooth sailing, that endear us to our vessels. I vividly recall the shaky-handed jury rigging that saved the rudder from compromising the hull after the top rudder bearing sheared off its bolts, 1,000 miles from land. Our makeshift repair held strong for the remainder of the journey. Once we arrived, I reinforced the new top bearing hardware by glassing in large gussets to support it.
Perhaps it’s the extensive labor we invest and the confidence that develops from it that makes parting ways so challenging. In those initial months after purchasing Journeyman, my parents helped with the varnishing, painting, rail re-bedding, and the V-drive rebuild. Those hours spent working on the boat with them turned into some of my happiest memories. Despite the heartache of letting go, I took comfort in knowing I was passing on a boat that was better for our time together.
From bluewater passages to day sailing, Journeyman never let me down. Often, I wonder if this is why so many marinas are filled with abandoned vessels. Fond memories compel people to cling to their boats long after they can adequately care for them, leading to feelings of guilt when their boats fall into disrepair. Letting go is truly a difficult process.
Soon after listing her for sale, a young, aspiring sailor from California purchased Journeyman, revealing that my farewell was near. Fortunately, he required delivery, granting me one last adventure to accompany this bittersweet transition.
Friday Harbor to San Francisco — A Final Adventure with Friends
The first crew members to sign up were Eric Cheong and Martin Gibson. Having shared over 5,000 miles with these gentlemen on various deliveries and races, I can’t think of better representations of integrity at sea. Both Eric and Martin embody seagoing gentility and support me in every way, from organizing meals to doing dishes. Martin has served as my first mate, crew member, navigator, fiberglass repair expert, and life coach during our double-handed Pacific Cup on my Moore 24, Evermoore. Eric joined us for a delivery from Hawaii the next year and has since been an outstanding guest on numerous boating trips. With such an incredible crew, we didn’t need anyone else, but the excitement of the passage made it hard to resist sharing the experience with more friends.
Next, we welcomed Har Rai Khalsa and Madison “Mad Dog” Rowley aboard. Har Rai once joined me on a short delivery from Port Angeles to Portland, asking to climb the mast as we sailed upriver. As a backcountry athlete and professional outdoor sports photographer, he brings an adventurous spirit and is always ready for anything, often with a cheerful grin.
Mad Dog is an unexpected nickname for such a sophisticated gentleman. We first sailed together in our teenage years during junior sailing camps in Portland. Our enduring friendship proves that bonds forged on water are unbreakable.
The last to join our charismatic crew was Kyle Hadley, whom I met through social media as he sought advice for his new-to-him Cascade 29. A self-taught sailor, Kyle is the youngest among us but possesses a commendable passion and curiosity about sailing, positioning him perfectly for what I call a seagoing apprenticeship. I’m confident that he will be one of the few who pursue the bluewater sailing journey that many dream about but never experience.
The Strength of a Cal 40
The timing and direction of this delivery promised exceptional sailing with Journeyman. Cal 40s thrive when the wind rolls in from behind, creating a magical sailing experience, especially when partnered with a following sea.
From Journeyman’s ship’s log on 9-9-20: The sun sets as we set up the 3/4 asymmetrical kite on the pole, surfing along at 11 knots. Meanwhile, Har Rai prepares a three-course Indian dinner, filling the cabin with delightful aromas. We’re thundering along about 10 miles offshore in 20 knots of wind, and the forecast looks promising. High-fives and good vibes flow freely.
The most captivating sea stories often involve challenges, but no sailor denies that those enchanting moments of harmony between sailor, boat, wind, and sea are what we truly cherish. Experiencing and sharing these magic moments with your closest shipmates far outweighs any mid-ocean head rebuild or the less enjoyable tasks of boat ownership.
It’s Not Just Smooth Sailing
Ship’s log 9-13-20: Thus far, we’ve been fortunate as we round the capes heading south. However, as we approach Cape Mendocino, we brace for challenging conditions. At sunset, wind gusts from the south reach 20+, creating a turbulent sea from the conflicting winds of recent days. I was in the port quarter berth when we dropped off a wave while on port tack, and the range came loose from its gimbals. Luckily, the solenoid was off, and the LPG hose was unharmed. We managed to secure everything in order to prepare dinner.
Ship’s log 9-15-20: Currently sailing dead downwind with the #2 jib poled out and the main preventer in place, gusts are now exceeding 25+, creating a difficult helm with a confused sea state. At 10 p.m., our helmsman backwinds the main, the preventer halts the jibe, but the boom vang breaks. Hours later during the following watch, the #2 backwinds one too many times and tears apart. No need to worry; it was an old sail. We switch to the #3 and fresh crew members take the helm.
Failures often occur at the boom and its components. The vang breaking reminds me of past difficulties with important rigging parts. The previous evening’s failure was a result of two rivets popping and the vang bending out of position. Fortunately, Marty devised a jury rig that managed to reshape it and slip it back into place with a lashing attached to an unused loop just aft of the vang attachment point. This fix mirrored one Martin executed during our race to Hawaii on Evermoore. A valuable lesson emerged: implementing fuses in rigging is crucial, and sturdiness isn’t always ideal. It’s always better to have a vang break than the boom, mast, or gooseneck. Such things occur; you jury rig solutions, and upon return to shore, you enhance the design.
Perhaps I’m a bit more invested than most in this lifestyle, but I don’t believe there’s anything quite like a boat and a sea voyage that can bring people together, pushing everyone’s boundaries and expanding their horizons.
As forest fires raged ashore and political dramas unfolded, our close-knit crew came together seamlessly. Watches operated smoothly, and everyone synchronized beautifully. I found myself secretly wishing we had farther to go.
Passing the Torch
Ship’s log 9-18-20: Now motoring through a pitch-black night as the wind dies down, and the smoke from the forest fires obscures any stars or moonlight. The phosphorescence trailing behind us is surprisingly bright. To add to the surreal scene, three Sooty Petrels have decided to join us in the cockpit. These small black birds appear unbothered by the crew and allow us to relocate them to safer areas aboard. Perhaps they’ve been attracted by the light from our navigation instruments.
The following day, the fog lifted, revealing the majestic Golden Gate Bridge. The entire crew gathered on deck as seabirds and whales danced around us, welcoming us as we glided under this iconic structure. Our journey neared its conclusion, and like all good things, it left a tinge of sadness.
Life often puts distance and years between us and our closest friends. Work, responsibilities, and family can complicate our connections with those who once played significant roles in our lives. This realization highlights the importance of adventures like this with friends. The time and financial investment in creating lasting memories fade quickly, but their essence remains forever. As we pass under the Golden Gate, returning to civilization, I find the clarity and mindfulness that comes from life at sea giving way to the worries and plans needed on land. My fellowship of seafaring brothers was dispersing, returning to their daily realities. The sadness of letting go of the boat paled compared to the joy brought by time spent with such incredible people.
As this chapter closes with Journeyman returning to California, where she was crafted, and I anticipate closing on a new teaching boat, a vital lesson crystallizes.
The memories and journeys we create are treasures beyond measure. The boat itself… well, that’s just material.
Unless stated otherwise, all photos in this article were taken by crew member and professional photographer, Har Rai Khalsa.
Note: This article originally appeared in the January 2021 issue of 48° North.
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Oliver Hayes, a seasoned sailor and marine journalist from Southampton, has a profound love for the sea that has shaped his career. Holding a degree in Marine Journalism from the University of Portsmouth, Oliver is celebrated for his compelling and insightful storytelling. His work vividly captures the excitement of sailing and the rich maritime heritage of the United Kingdom, making him a respected figure in the sailing community. When not writing, Oliver enjoys exploring the British Isles’ diverse coastlines and participating in local regattas, always on the lookout for his next nautical adventure.
