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Why Sail?

Is it luxury? Speed? Or what is it? During hundreds of interviews, podcasts, and discussions about why people sail, reader and Golden Ticket winner Jamie Rosen expressed the sentiments we hear so often when he responded to our questions about his recent win. When asked about what he likes about sailing, he responded, “I love how it slows you down, keeps you in the moment, connects you to nature, and always teaches you something new, no matter how long you have been at it.” We couldn’t agree more. We thought about this on a flight when we saw the earphone package below. For most sailors, sailing is about tuning in, not tuning out. It’s not about speed or luxury. It’s about connecting to people and the planet.

The message of tech is to tune into your screens and tune out of life.
The message of tech is to tune in to your screens and tune out of life.
© 2026 Latitude 38 Media LLC / John

The common threads we find among sailors are adventure, exploration, challenge and connecting with friends, family and nature. Josh Kali said, “The most amazing part for me, as many solo sailors who have done long ocean passages can attest, has been the tranquility and solitude of the open ocean,” and added, “Finding a deeper connection with this incredible planet we inhabit by learning to live in harmony with the ever-changing sea, making friends (and sometimes enemies) with innumerable clouds, waves and every gust of wind, has borne in me an insight into the dynamic, often capricious nature of our environment. Seemingly countless days of immaculate azure skies, breathtaking tangerine sunsets, and a blanket of nearly infinite stars, glittering on the indigo sea like a king’s ransom of diamonds, [have] helped me to understand how truly lucky we are to be here.”

Josh, aboard his 19-ft one-design, Skookum, is currently heading to Antigua to complete his circumnavigation.
Josh, aboard his 19-ft one-design, Skookum, is currently heading to Antigua to complete his circumnavigation.
© 2026 Josh Kali Racing

One thing we’ve never heard is anyone saying, “I love sailing because of the luxury.” Really, does anyone sail because of luxury? Judging by much of the world’s marketing these days, you’d believe luxury is one of the most important aspects of life and sailing. Luxury is boring. Hearing Commodore Tompkins’ stories about sailing on Wander Bird or Flashgirl is far more interesting and completely devoid of luxury. Read the story on “Why I Sail” from Webb Chiles, or our recent story on Josh Kali, who has been sailing around the world on a 19-ft plywood boat.

Why has Webb Chiles sailed hundreds of thousands of miles in a wide variety of mostly small boats?
© 2026 Courtesy Webb Chiles

We recently heard a story from someone describing her first sailing experience. It went like this: “I was invited to go out for a sail on the Bay, and being new, I showed up at South Beach Yacht Club in my jeans and best cotton summer sailing apparel. It turned out my first sail was going to be a race on a J/105 on Berkeley Circle. During a very windy, cold, wet race, a halyard went up the mast. I was asked to ride up in the bosun’s chair to retrieve it, and up I went. While [I was] up there, we took a knockdown, almost putting me in the water. We recovered, finished, and I made it back to the docks. I loved it all and was hooked!” That experience may not thrill everyone, but between the excitement, solitude, nature and slowing down, people find many good reasons to sail.

Stepping off the land and getting onto the Bay opens a world that is close by, and worlds away.
© 2026 Simone Staff

Despite the foiling frenzy and the spectacles of SailGP and the America’s Cup, we think most people see sailing as an opportunity to slow down. Racing is a ton of fun, but most sailors are cruisers or daysailors. The weekend sail with family and friends is a time to disconnect from devices and be in the moment. It’s also amazing how exciting it can be racing at 4.5 knots during a close rounding in the Mercury, Snipe or Knarr class. Anchoring out in Clipper Cove, Horseshoe Cove or Aquatic Park dramatically shifts your perspective on life in the Bay Area.

SV Gemini
Sonya David and Jack Patton aboard Gemini in Horseshoe Cove.
© 2026 Two the Horizon

The America’s Cup and SailGP believe speed is the secret to getting an audience and more sailors. But why do people watch curling in the Olympics? Why do people watch golf on TV? In fact, you can watch people play darts, poker or chess on the screen. They’re all incredibly slow activities. We think speed is irrelevant, and it’s the human dimension that makes any competition compelling. As SailGP and the America’s Cup have increased the role of technology and reduced the role and visibility of humans, they have lost human connection.

Who wouldn't want to be part of a sailing team on San Francisco Bay?
There’s something fun about sailing. We hope you find it on the Bay and in the pages of Latitude 38.
© 2026 Erik Simonson / Latitude 38

Connection is the other great reason people sail. The sailing community is full of fun and interesting people. They are people with a passion for the act of sailing, the connection built among crew or the connection to the natural world. They know the outdoors is where life happens. Whether you drop your hook up in the Delta, in the Sea of Cortez, or in Fiji, you’ll quickly find yourself connecting to an interesting community of fellow sailors. The most compelling reasons to sail are often overlooked by modern marketing and marquee events like the America’s Cup. When you unplug and tune in aboard a sailboat, you’ll find the reasons people have continued to sail over the centuries. Why do you sail?

Want to connect to sailing and sailors? Come to our Crew Party at the Golden Gate Yacht Club on Thursday, March 5.

P.S. Curiously, after I’d written this story “Why Sail?” my wife was listening to an interview with author Caroline Paul about her book Why Fly on KQED’s Forum. The call-in program’s first caller was a sailor, Lindsay from Richmond, describing the parallels between flying and sailing. Both the author’s and Lindsay’s comments echoed the sailing quotes above. Lindsay, are you reading this? Your comments really resonated with us. You can listen to Lindsay’s comments about sailing starting at about minute 16:05 on Forum here.

 

1 Comment

  1. David Fritz 3 hours ago

    For me it’s a ZEN thing. The best time is Sunset out in SF Bay; I sail back and forth between Alcatraz and Angel Island looking out towards the Golden Gate Bridge.
    Folks will ask me “Dave, what do you do out there?” I respond with “I excel at going nowhere slowly!”

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