Sailing the Puget Sound with Captain Ben Doerr

Adventure |

Words by Andy Cochrane. Photos by Andy Cochrane and Johnie Gall.

As the wind picked up late in the morning, Ben Doerr’s eyes started to glow. At roughly six knots, we’d soon be under sail. Orchestrating a handful of people through a web of rigging and deck lines, Ben patiently coached us through untying our ship from its mooring ball, raising the sails, and sitting back to let the wind do the rest. All the while, he stood at the helm of his sailboat, True, beaming.


Ben wears the Teva Men’s Original Universal in Peaks Black while managing the rigging on his sailboat, True.

Ben and I met through mutual friends a few years ago, a serendipitous connection that’s transformed into a lifelong friendship. I’ve learned a lot by being around him, from important life lessons to fun anecdotes about his meandering life on the water. There are the basics – he loves meeting new people and he’s terrified of the dark – but there have also been deeper lessons. I’ll get into those in a moment.


Ben attributes his love of sailing to his grandfather, who took him out his first few times on a sailboat, a 19-foot daysailer called Vixie. “I think my deep and unshakable adoration for my grandfather is what really drives my love of sailing, even now, but certainly early on,” Ben says.


The Teva Ember Moc was a favorite among our sailing crew. It’s cozy for colder mornings on the water, but still offers enough traction for walking around on deck.


After those first few sails, Ben didn’t set foot on a boat again until a friend invited him to crew on a racing team out of Traverse City, MI, the summer after he graduated from high school. Later, Ben went on to work at a summer camp in Maine, where he was allowed to helm a few small boats, and eventually he moved to Bainbridge Island in Washington, where he purchased his first watercraft. Ben and his wife, Deb, continued to purchase progressively bigger boats, ranging from 22 feet to 28 feet, but it wasn’t until after a two-week stint cruising the San Juan Islands that they decided to get really serious about sailing as a business opportunity. well, as far as boats go.


The couple wanted a boat they could live on and that could carry them safely to Alaska or Mexico, if they ever decided to do so. The catch? They couldn’t afford anything like it. Instead of giving up the dream, Deb proposed an idea: “What if you got your license and chartered the boat to pay for it?” The rest is history: Together, Ben and Deb just wrapped up their third season running Sail Bainbridge, a charter business offering sails ranging from two hours to multiple days leaving out of a harbor on Bainbridge Island.


A few days earlier, Ben, myself, and a few friends of ours had set sail from Bainbridge, a harbor town just a short ferry ride from Seattle. It was the end of the sailing season and Ben wanted to sneak in one last multi-day sailing adventure. Within minutes of texting me the idea, we had a crew assembled and dates on a calendar. This wasn’t an opportunity to pass up.


Instead of heading north to the fabled San Juan Islands, we broke suit and pointed True south, toward the less traveled but equally stunning southern end of the Puget Sound. A ragtag group of friends on an adventure, we packed light—not one of us with much more than a change of clothes, a swimsuit, a guitar, and ample beverages for evening merriment. Our only aim was to take a break from the daily grind, learn a bit about sailing, and explore this new territory. And, of course, spend quality time together.


Pictured: the Teva Men’s Ember Moc.

As the sails started to fill and the ketch began to pick up speed, I asked Ben what he liked most about sailing. His answer was pretty simple: “Sailing is magical. I mean, I understand the science, but I still feel the magic. Wind is moving you. There’s a peacefulness to it, a tranquility that can’t be matched, at least in my mind.”


We bantered for a while, watching our friends find spots to sit in the sun. Ben looked back at me and said, “I love how everyone has the same reaction to the engine turning off and the sails filling with wind. There is an audible sigh and it completely transforms whatever is going on in each of us. It’s like a switch that flips from ‘busy’ to ‘relax’.”


Our crew also wore the Men’s Hurricane XLT2a rugged, grippy sandal that performed well when we wanted to go ashore.

He was right. My mood adjusted almost instantly. It gave me pause, and I began to reflect on the other lessons I’ve picked up from Ben and our time on the water together.
Lesson 1: Never take yourself too seriously. Racing tides on our way through the Tacoma Narrows, Ben slowed the boat, cracked a small grin, and posed an idea: “Think you could surf behind the boat?” It was a reminder to enjoy and immerse myself in the present, even on a long journey with a distant goal. Within a minute, we had a paddleboard in the water and three of us clambered onto it. With a fixed line tied to the stern of True, a bit of balance and a lot of  luck, we managed to all stand up on the board and surf our way into the annals of sailboat history. Or at least, True’s history.


Lesson 2: Wear your heart on your sleeve. Whether he’s talking to a stranger in a coffee shop or his own wife,Ben never holds back. He’s real and raw with everyone, and small talk quickly turns into deep conversation. Short stories grow into heartfelt tales, told with thoughtful characters. A modern-day bard, Ben sings from the heart, laughs from the belly, and cares for everyone he meets.


Lesson 3: Embrace a new speed of life. Our first morning on the water was cool and misty. I was up early, eager to explore. Ben was also up early, but unlike me, he wasn’t in a rush. Ben was sitting on deck, just observing. Not looking at anything in particular, just casually scanning the calm water, taking in the quiet moment. An hour later we made coffee, swam, and enjoyed a leisurely breakfast. The breeze was light and our agenda was flexible – and I got a good taste of what it means to slow down.


Lesson 4: Laughter really is the best medicine. Leading up to our trip, I’d had a hectic couple of weeks. Big work projects and heavy family news had layered a considerable amount of stress on me. It was nice to unplug and be present for a few days with good friends, sharing stories and airing some of these tensions. But what truly helped me reset was laughter. From bad whale jokes to snarky quips about politics, I found solace in flipping hardships into humor.



Lesson 5: Chase your passions. Ben fell in love with sailing as a kid in Florida and never looked back. He’s been part of competitive racing teams, worked as a crew member on a number of boats, and now owns, maintains, and captains TRUE. Many things have changed in his life, from the place he calls home to how he makes his money – but his love of boats has stayed the same. He’s happy on the water, sailing, adventuring, and teaching others. Watching that passion inspires me to keep chasing what I love, too.


Bonus Lesson: If this lifestyle sounds appealing and you want to charter a boat with Ben, visit Sail Bainbridge.


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