Sailing Doodles Podcast

For most of human history, people who felt trapped by their circumstances could leave everything behind and head toward a new frontier. They could escape their social class, family reputation, past failures, or limited opportunities and try to build something entirely new. But do those kinds of fresh starts still exist? In this episode, I explore why starting over may be harder ...

In this Ask Me Anything podcast, I answer some of the questions patrons and viewers have been asking most. I start with Nika—whether she’ll be joining me again, how we got along, and what might be next. I also share the scariest experience I’ve ever had at sea: the night my old boat nearly caught fire and sank near Cape Hatteras. I included clips from the original video and expl...

Owning a brand-new hybrid-electric yacht has been exciting—but it has also come with a much steeper learning curve than expected. In this podcast, I give an honest update on my first few weeks aboard the Island Spirit 525e. I walk through the technical issues we’ve experienced so far, including repeated generator faults, problems within the drive-battery system, charging limitat...

I’m back with the second half of my patron Q&A, and this time we’re talking about what kind of boat I should buy for my next adventure. Would a diesel Sea Ray-style express cruiser work for Florida, the Keys, the Bahamas, and potentially farther into the Caribbean? Or would I be better off with a trawler, a traditional motor yacht, or something designed for longer-range crui...

A few weeks ago I shared an idea that I thought could completely change the way people experience luxury sailing. Then I asked for your feedback. Hundreds of comments later—and one incredibly detailed blog from a viewer—I realized I had made some major mistakes. In this episode I explain what I got wrong, why the original model probably wouldn't work, and the new direction I'm c...