One Mile at a Time:
How Phoebe Wittbeck turned experience on the water into an opportunity to help others find their own.

There’s a moment in every sailor’s journey when experience stops being something you’re collecting and starts becoming something you can pass on.

For Phoebe Wittbeck, that journey began long before she became a professional captain.

She grew up in Michigan, sailing small boats on the lakes from around eight years old. But the idea of going further was always there. Before Phoebe was born, her parents spent four and a half years circumnavigating the world, and she grew up surrounded by their stories. By 13, she was reading about offshore sailing and plotting her own route around the globe.

The ocean, however, was still a long way from Michigan.

FROM THE LAKES TO THE OCEAN

Phoebe followed a path that will sound familiar to plenty of sailors. She raced small boats, became a sailing instructor and, after moving to North Carolina for college, found work around the local sailing and charter scene.

Crew work followed. Then deliveries. More miles. More responsibility.

During COVID, Phoebe earned her captain’s licence. By 20, she was taking charge of boats herself.

The transition wasn't simply about gaining a qualification. It was about becoming comfortable with responsibility: docking in current, making decisions with guests aboard and knowing that, ultimately, the boat and everyone on it were now looking to her.

Phoebe remembers changing the way she thought about docking in particular. Instead of something intimidating, it became “a little puzzle.”

That confidence wasn't built overnight. It came from doing it again and again.

And the miles kept adding up.

WHEN EXPERIENCE BECOMES VISIBLE

As Phoebe's sailing grew, she began recording her time on the water through SeaPeople.

Trips, tracks, miles and the little stories behind them gradually became something more than a logbook. They created a visible record of the sailor she was becoming.

And someone was paying attention.

Phoebe had crossed paths with the team behind Outer Passage, but there had been little contact beyond following one another online. Months later, they reached out about an opportunity.

What they remembered wasn't a polished résumé. It was how she sailed.

One SeaPeople track in particular had caught their attention. Aboard her previous boat, Phoebe had been sailing upwind through Drake Passage. Rather than turning on the engines, she tacked back and forth at production-catamaran angles and kept sailing.

It was a small decision on one passage, but it showed Outer Passage something important about the kind of sailor she was.

In Phoebe's words,

SeaPeople was

“the whole reason I got this job, really.”

Experience only matters if you do something with it. Phoebe accumulated it.

SeaPeople made it visible. Outer Passage recognised it. Now aboard Tiger Lily, she's passing it on.

ABOARD TIGER LILY

Today, Phoebe works with Outer Passage aboard Tiger Lily alongside Perrine Louvet, her fellow captain and crewmate featured with her in the SeaPeople interview.

Tiger Lily is a Balance performance cruising catamaran carrying a full inventory of Ullman Sails, and together Phoebe and Perrine are giving the sailors who step aboard an opportunity to build genuine experience of their own.

The learning happens where it matters: at the helm, on the sheets, reading conditions and becoming increasingly comfortable with the decisions that come with handling a performance cruising catamaran.

And for Phoebe, one particular moment aboard Tiger Lily brought her journey full circle.

Her favourite spinnaker hoist on the boat is still the very first.

By chance, they were back in the same stretch of water where Phoebe had made all those tacks aboard her previous boat, the sailing that Outer Passage had noticed through SeaPeople.

This time, she was aboard Tiger Lily.

The kite went up cleanly. The owners stared at the sheer size of it. Tiger Lily loaded up and accelerated, quickly sailing past another boat at more than 10 knots.

Phoebe remembers the feeling simply:

“Pure joy!”

Same waters. A very different boat. And a pretty remarkable reminder of just how far those earlier miles had carried her.

YOU WILL CONTINUE TO EARN IT

Phoebe's story is impressive on paper. A captain at 20. Thousands of miles sailed. Offshore passages and professional skippering while still in her twenties.

But perhaps the most telling part of her SeaPeople interview comes when she's asked what she would tell her younger self.

Phoebe admits that she struggled with feeling as though she wasn't qualified enough or didn't deserve the opportunities coming her way.

What would she tell that young captain now?

“You will continue to earn it.”

Five words that say a great deal about sailing.

Experience isn't something you suddenly have. You build it every time you leave the dock, make a decision, get something wrong, learn from someone else or take responsibility when it matters.

Then, if you're lucky, there comes a point when you get to pass some of it on.

For Phoebe, that next chapter is already underway aboard Tiger Lily.