There’s always that moment, right after the lines are cast off, when reality sneaks up and taps you on the shoulder with a greasy finger. This time, it tapped Woody.
Woody Henderson, age twenty-five, freshly escaped from behind a bar where drinks were cold and life made sense in ounces and tips. He stepped aboard LOST SOUL looking like he’d wandered off the set of a sitcom and into a floating question mark. Somewhere between Redondo Beach and “what the hell did I just sign up for,” he muttered the phrase that has launched a thousand questionable adventures:
“What have I done?”
Perfect. He was going to fit right in.
We had a plan. Not one of those tight, laminated, color-coded plans. More like a drifting thought with a flavor. This one tasted like garlic, grilled meat, and cheap wine.
Souvlaki.
And not just any souvlaki. The kind you find in Sounion, near the Temple of Poseidon, where the gods themselves probably wander down for lunch when Olympus gets boring.
So naturally, we pointed the boat… south.
Because every great journey to Greece begins by heading in the opposite direction.
At 10:30 a.m. on October 25, we actually did something shocking.
We left on time.
Lines off. Engine rumbling. Dock shrinking behind us like a bad habit. No drama, no last-minute disasters. Frankly, it was unsettling.
We made the grueling 24-mile passage to Catalina like seasoned explorers, which is to say we drank, laughed, and pretended we were crossing an ocean instead of hopping a puddle. One last night at the Isthmus saying goodbye to friends, then the epic 10-mile odyssey to Avalon.
It was in Avalon that Woody and Jody met one of the most dangerous creatures known to man:
Me, behind the wheel of a rented golf cart.
Now, those little electric carts come with governors. Sensible devices. Designed by people who hate fun. Turns out, gravity does not respect governors.
We crested a hill.
We descended.
The cart screamed like a banshee discovering espresso. Woody and Jody clung on with white knuckles and wide eyes as we achieved what I can only describe as “golf cart enlightenment.”
Sometimes life hands you a downhill slope and says, “Go ahead… let’s see what you’re made of.”
We obliged.
Dave Bean joined us next. Teacher, sailor, and a man who would soon regret trusting us. By 4 p.m., we waved goodbye at the fuel dock and headed toward foreign waters.
Seventeen miles later, we were in Mexico.
International voyagers. Just like that.
We anchored at the Coronado Islands under a sky that looked like it had been hand-painted by someone who understood romance. Stars everywhere. The kind of night that makes you forget land even exists.
The next day was all sunshine and easy sailing until Santo Tomas decided to remind us that the ocean has a sense of humor.
We pulled in. The wind cranked up to 28 knots like someone flipped a switch labeled “mess with them.” Suddenly, loose gear turned into airborne projectiles. Our brand-new bean bag chair made a heroic leap for freedom and vanished into the deep.
We mourned.
Briefly.
Then we moved four miles down the coast and carried on, slightly less comfortable and a lot more aware.
Somewhere along the way, the autopilot died.
At first, it felt like losing a limb. Then something strange happened.
We started sailing again.
Actually sailing. Feeling the boat. Listening to her instead of bossing her around with buttons and wires. Turns out, when you remove the automation, you get the soul back.
Funny how that works.
At Cedros Island, we anchored near a colony of sea lions engaged in what can only be described as a full-blown aquatic love festival.
The noise was… enthusiastic.
As darkness fell, the pups took to the water, zipping around the boat, leaving glowing trails in the phosphorescence like underwater comets. It was part nature documentary, part psychedelic flashback.
If the ’60s had a marine sequel, this was it.
We traded a six-pack of beer for a six-pack of lobster, which might be the most civilized transaction in human history.
Add a calico bass Dave caught, some homemade bread, and suddenly we were dining like kings who forgot to pay taxes. We invited neighbors over, feasted under the stars, and for one perfect evening, everything lined up just right.
Of course, that’s usually when things go sideways.
A few days later, they did.
The morning started innocent enough. Calm seas. No wind. Easy motoring. Then the wind showed up.
From the south.
Now, down there, the wind coming from the south is like your dog suddenly speaking French. It’s not supposed to happen, and you immediately suspect trouble.
For the next 36 hours, we punched straight into 30 to 35 knots. Waves stacked up. Progress slowed to a crawl. At one point, we were moving at 0.8 knots.
That’s not sailing. That’s stubbornness with a motor.
It turned what should’ve been a pleasant trip into a full-blown mechanical exorcism. Eventually, we crept along the shoreline, hiding from wind that refused to be hidden from.
When we finally limped into Cabo, it felt like crawling into a bar after a bar fight.
And Cabo, being Cabo, welcomed us like we never left.
Familiar faces. Cold drinks. Stories already growing taller by the minute.
“Short Wave” Dave flew in with a new autopilot. Two hours after landing, it was installed.
Two hours.
Which meant, naturally, it was time to do something incredibly stupid.
Thus was born the First Annual Short Wave Dave Cabo San Lucas Backward Body Surfing Championships.
Rules were simple. Stand waist-deep. Wait for a boat wake. Fall backward. Let physics and poor judgment do the rest.
Winner: whoever collected the most sand in their shorts.
Jody won.
Decisively.
We did not ask questions.
Dan the Slug Man joined us next. Mentor, tormentor, perfectionist. A man who believed things should be done right.
A philosophy I have always found… negotiable.
He tried to refine my craftsmanship. I responded by embracing my inner “good enough.” It drove him crazy. Which, frankly, was half the fun.
We left Cabo at 5 a.m. for a 230-mile run to Isla Isabella, and for once, the ocean decided to cooperate.
Twenty knots of wind. Steady. Clean. Beautiful.
We flew.
Nine to eleven knots for twenty hours straight. The boat humming, slicing through water like she remembered why she was built.
It was sailing in its purest form.
No drama. No chaos. Just motion and wind and that quiet grin that creeps across your face when everything finally clicks.
At Isla Isabella, we wandered among frigate birds. The males puffed up these ridiculous red throat balloons to attract females.
Naturally, we tried it ourselves.
The results were not encouraging.
Jody laughed.
We retired from courtship displays.
Later, out on the dinghy, we drifted near a group of humpback whales. Engines off. Silence.
They came within 30 feet.
Massive. Calm. Ancient.
Just rolling, breathing, existing in a way that makes you feel very small and very lucky at the same time.
No jokes. No noise.
Just awe.
From there, it was Chacala. Fresh dorado for dinner. Fireflies dancing in the dark. Cold beers on a quiet beach where time seemed to take the night off.
Puerto Vallarta came next. Marina chatter on the radio. Familiar voices. The strange comfort of being remembered.
Not always a good sign.
Then Jim showed up.
Chronologically over seventy. Mentally somewhere between sixteen and arrested development.
Which meant he was perfect.
Because out there, age doesn’t matter much. What matters is whether you’re willing to laugh when things go wrong, raise a glass when things go right, and climb aboard knowing full well you might end up somewhere completely different than planned.
Like Greece.
Eventually.
Maybe.
