Finding Real Joy in Boat Ownership

Whether or not you’re in the market for a boat, boat shows always offer an electric atmosphere for likeminded cruising enthusiasts. Courtesy Annapolis Boat Show

Take a stroll down the docks at any boat show, and you’ll likely hear the classic quip: “The two happiest days in a sailor’s life are the day he buys the boat and the day he sells it.” While that might get a chuckle or two, for some of us, it’s more cringe than comedy. 

Boat ownership is like parenthood—exhilarating, but with challenges. Sure, the day you buy your boat feels magical, but the real hocus pocus happens when you launch it. I’ll always remember the day we took our 31-foot Hunter, Ragtime, off its mooring for the first time: engine purring like a contented cat, sails popping open and filling with life, wood creaking and rigging shifting as we heeled over on a close reach.

Our first shakedown cruise was up the Connecticut River to Hamburg Cove, where we anchored under the stars on a sheet of glass, my family and I sharing laughs and lobster bisque by the light of an oil lamp. It seems like yesterday. That, friends, is what boat ownership is all about. 

Now, selling a boat? That’s another story. When we finally waved goodbye to Ragtime more than 20 years later, it felt like parting with a family member. Every imperfection told a story—like the not-quite-white patch of cockpit nonslip where red wine was spilled one fuzzy evening on the hook in Fort Lauderdale, leading to a strict “no red wine aboard” policy. Ragtime was a floating scrapbook of memories. 

The infamous quip about the two happiest days probably came from someone who bought a fixer-upper and expected smooth sailing. Newsflash: Boats need TLC. A boat owner often has to channel their inner MacGyver to plug leaks, protect the gelcoat, keep the sails and rigging in good working order, and ensure that the engine runs smoother than a Steely Dan guitar solo.

Upkeep can be pricey if you’re not handy, and a boat’s initial charm can mask a lot of hidden issues. Excitement can quickly become frustration as maintenance costs soar. I get that. You probably do as well, which is why most of us learn to love the smell of marine grease in the morning and to find joy in every successful DIY repair. (If you know, you know.) 

If you’re already a boat owner, or are thinking of becoming one this fall boat-show season, the September 2024 issue of Cruising World has you covered—starting with marine industry veteran Ralph Naranjo’s guide to boat-show shopping, intended to help you navigate the often-overwhelming experience on the docks and ensure that you end up not just with a boat that you love, but also with one that meets your needs and dreams.

Beyond the buying and selling process, boat ownership is more about the journey itself. Courtesy Annapolis Boat Show

Also in the issue, off-grid adventurer Hilary Thomson’s “The Bricolage of Boating” delves into the art of DIY projects and how they bring sailors together as a vibrant cruising community. Cruising legend Jimmy Cornell, in “Chasing Perfection,” describes his five attempts to build the perfect cruising boat, giving us all a masterclass in perseverance and passion. And, with an active hurricane season upon us, sailing veteran David H. Lyman’s “Riders on the Storm” is a must-read firsthand account of surviving Hurricane Hugo that offers vital insights and a sobering reminder of the power of the sea.

While the adage about the happiest days might ring true for some people on the docks this season, it misses the heart of the matter. For die-hard sailors, the happiest days are the ones spent on the water.

My advice? The next time you hear that saying, just smile and keep your eyes on the horizon. Because for us boaters, the real happiness lies in the journey—not just the destination.

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