The Curious Case of Dan: A Crew Story We Never Expected

Every boat has its characters, and every voyage writes its own chapters. Some are heart-expanding, some are humbling, and some… well, they leave you tilting your head, replaying events, and quietly asking, What actually happened here? This is one of those chapters.

Earlier this year, before Houdini was even fully back under us, an email landed in Aubrey’s inbox at the exact moment she needed a reminder that strangers out in the world believed in her. His name was Dan. His message was heartfelt, supportive, and simple: if we ever found ourselves taking on extra crew, he’d love to throw his name in the hat. He said he’d roll up his sleeves, contribute to costs, and be part of the adventure.

The timing wasn’t right then, but he checked in over the months. And by late summer — when we were back aboard Houdini and preparing for the long, ambitious run toward Panama — the timing surprisingly was right.

After a video call and plenty of messages, we said yes.

Dan’s background was eclectic and interesting: German, once an anesthesiologist, later in corporate life, then a full pivot to owning a döner kebab shop in Hawaii, which he eventually sold before moving to Chile to manage farmland. He was tidy, polite, eager, and receptive to the constant teasing Aubrey and I tossed at him. He fit in almost immediately, and we even joked about hiding his passport so he couldn’t escape us.

In the beginning, Dan was exactly what you hope for in new crew: helpful, respectful, willing to learn, adaptable to the strange rhythm that is boat life. And in truth, we thought we needed him. Three women aboard a 51’ ketch with a baby, preparing to sail thousands of miles, makes you feel like having a man onboard is “the smart thing.” A little backup muscle. A little security.

Everything was smooth — until one night, two weeks before everything unraveled, when Dan overindulged. We were docked so nothing dangerous happened, but the situation that unfolded was enough that Aubrey had very firm words with him the next morning. He apologized sincerely, agreed it couldn’t happen again, and life went on.

And it really did seem to return to normal. For two full weeks, things felt back in rhythm. We worked together, laughed together, cooked together, repaired things together. There was no tension. No warning signs. No indication of what was coming.

Then came La Manzanilla.

We ended up unexpectedly stuck there waiting on a part — a full seven days longer than planned. Sometime during that week, Dan mentioned his foot was a bit swollen. Not alarming, just uncomfortable. He went to the small town doctor, who recommended he travel to a slightly bigger town the next day for imaging. The taxi ride was long — nearly ninety minutes each way — and he was gone the whole day.

That evening, as we were eating dinner in town, Dan walked in to tell us he had arranged a car to take him all the way back to Puerto Vallarta that night — a four-hour trip. He wasn’t sure how long he’d be gone, he said, so he was packing heavy but leaving a few things behind.

When we returned to Houdini later that night, we learned what “leaving a few things behind” meant: nearly everything was gone. Only a handful of unimportant items remained.

And that’s when the story took a sharp turn into the bizarre.

Over the next few days, the messages we received were sparse, scattered, and increasingly strange. Long stretches of silence. Elaborate medical explanations. Overnight hospital stays. Huge bills. Then more silence.

At one point we hadn’t heard from him for almost 24 hours, and concern took over.

We called hospitals in Puerto Vallarta.

We posted in local Facebook groups.

Nothing. No record of him anywhere.

Eventually he messaged: he paid for “extra discretion,” he said, and that’s why hospitals couldn’t confirm anything. He told us he would be flying on a private jet to Mexico City the next day for cardiology tests. The medical bills were skyrocketing. Everything sounded urgent and dramatic — yet nothing fit together cleanly.

That was also the moment we realized he did not have travel insurance.

And watching this unfold in real time — watching someone get swallowed by medical costs, uncertainty, and confusing care far from home — reinforced something we already practice: never, ever travel without insurance. It’s exactly why we use SafetyWing. We’re not invincible out here; none of us are. Unexpected things happen. And the difference between chaos and stability is often one policy.

When we gently questioned whether he might be getting taken advantage of — or whether the process seemed odd — the tone shifted. Suddenly he announced he was checking himself out, in the middle of the night, and flying straight home to Germany.

Just like that, he was gone.

No proper goodbye.

No closure.

No explanation that truly made sense.

Just an empty bunk and a hundred unanswered questions.

In the days that followed, we tried to piece it all together. Was he telling the truth? Did he panic? Was he overwhelmed by boat life? Homesick? Embarrassed by the drinking incident? Was this a silent exit strategy? Or was something genuinely wrong?

We will probably never know.

But we do know this: his departure revealed something we should have known all along.

As the three of us — three women and a baby — settled back into our natural rhythm, the boat felt lighter. We were working better. More in sync. More confident. And suddenly the “need” for a man aboard felt like an old belief we had simply outgrown.

We realized we were always capable of doing this journey ourselves.

We didn’t need Dan.

We only needed each other.

Dan’s chapter in our story was short, strange, and filled with mystery. But his absence taught us something his presence never could:

We were built for this — just as we are.

And with that clarity, we keep sailing south. Three determined women. One curious baby. One old pirate ship. And a horizon full of the unknown.

Adventure continues — twists, turns, mysteries and all.

We’ve chosen to collaborate with SafetyWing because having travel medical insurance is something that makes sense for how we live and travel long-term. If you’d like to learn more about SafetyWing Travel Medical Insurance and decide whether it’s right for you, you can find more information through our link.