Why I’m Selling My 56-Foot Sailboat

It probably looks like my 56-foot CT56 is falling apart, but there’s more to the story. After sitting on the hard unattended for over a year, I’m compressing a year’s worth of maintenance into just a few weeks. In this episode, I break down what’s gone wrong, what I’ve fixed, what still needs to be done, and why I’ve decided it’s time to sell Nauti Dogs. I’m ready for something different — a smaller motor yacht for cruising Florida, the Bahamas, and maybe the Great Loop. The listing for sale https://www.boattrader.com/boat/1989-ta-chiao-ct-56-10282803/

Before Sailing Doodles, I spent years flying Gulfstream private jets around the world, and for about six to eight months I was one of the primary copilots flying Aerosmith on tour. Most nights we'd watch the show, leave halfway through to get the jet ready, then fly the band to their next city as soon as they came off stage. But one night, flying Aerosmith home to Boston, I noticed something strange in the cockpit. One of our fuel temperature gauges was climbing rapidly—and eventually pegged at 110°C. There was no warning light. No alarm. And Aerosmith had no idea anything was wrong. In this episode, I tell the story of what it was really like flying Aerosmith on tour, what happened that night, and how we got them safely home without the band ever knowing there was a problem.

In this episode I’m answering your questions about what’s happening with my electric catamaran, whether I’m keeping it, selling it, or moving back to diesel.

Back in 2004, I was a young Gulfstream III copilot flying celebrities around the world—and one of our regular passengers was Snoop Dogg. On one particular trip, our company was bringing Snoop and his entourage home from Brazil. I joined the trip in Brownsville, Texas, where the airplane had to clear U.S. Customs and Immigration before continuing on to California. Customs knew who was coming, and they were ready. Officers met the airplane with a drug dog and thoroughly searched the jet. They even tested the dog during the inspection. Nothing was found, everyone cleared Customs, and we departed for California. Then, shortly after takeoff, I smelled something coming from the back of the airplane that sure smelled like marijuana. To this day, I have no idea what actually happened. I never saw anyone with marijuana, didn't know of anything being aboard, and don't know whether what I smelled had ever been on the international flight. But after watching that Customs inspection firsthand, I remember sitting in the cockpit thinking, “How the hell is this possible?” In this episode, I tell the full story, along with what it was like being a young charter pilot flying Snoop Dogg and other celebrities during one of the wildest periods of my aviation career—and why I'm glad smartphones weren't around back then.

What is it actually like to own a superyacht? I sit down with my friend Bob, who has owned yachts ranging from 65 feet all the way up to 165 feet, to get an inside look at the reality of superyacht ownership. We talk about what these boats really cost to buy and operate, hiring and managing crew, maintenance, scheduling, fuel, marinas, itineraries, and all the logistics that come with owning a yacht of this size. If you’ve ever dreamed about owning a superyacht—or just wondered how the ultra-wealthy actually manage these massive boats—Bob gives a candid look at everything that goes on behind the scenes. From a 65-foot yacht to a 165-foot superyacht, how much does the experience really change, and at what point does owning a yacht become more like running a business? Check out Bob's boats for sale: The Horizon 94: https://alliedmarine.com/used-yachts-for-sale/2005-horizon-94-ft-yacht-for-sale-9284132/ The Pershing 70: https://s3.amazonaws.com/boss.yatco.com/Account/17560/Files/f832b6f6-1f8a-4188-91a1-92c2ae22241d/BAD_DADDY.pdf Here is the link to my CT56 for sale: https://www.boattrader.com/boat/1989-ta-chiao-ct-56-10282803/

I’m recording this episode from the roof of my RV in the middle of Black Rock City at Burning Man 2026. Burning Man has grown from a small gathering on a San Francisco beach into a temporary city of more than 70,000 people in the Nevada desert. But after decades of explosive growth, something is changing. Tickets that once sold out almost instantly are now easier to get. The average Burner is getting older, fewer people in their 20s are attending, and the cost of participating continues to climb. At the same time, the nonprofit organization behind Burning Man reported a loss of more than $10 million in 2024. In this episode, I look at the history of Burning Man, how it became what it is today, and some of my own experiences attending the event. Then we dig into the numbers: attendance, ticket prices, demographics, rising production costs, and Burning Man Project's finances. So is Burning Man actually dying? Has it simply become too expensive for a younger generation? Or is this just the natural evolution of an event that's been around for 40 years? And most importantly—what does Burning Man actually feel like in 2026? Recorded from Black Rock City, Nevada.

In this episode, I sit down with Gabriel, whose list of adventures is almost hard to believe. Most recently, he completed the legendary Northwest Passage aboard a 48-foot steel-hull trawler, navigating some of the most remote and challenging waters on Earth. But that’s only one chapter of his story. He has also circumnavigated the globe on a 48-foot sailboat, climbed Mount Everest, completed the Seven Summits, and swam the English Channel. We spend nearly an hour and a half talking about what it actually takes to attempt adventures like these—the preparation, the danger, the moments when things go wrong, and some incredible stories from places very few people ever get to experience. We talk about sailing through the Arctic, climbing the highest mountains on every continent, crossing oceans, swimming the English Channel, and what keeps someone searching for the next big adventure after already accomplishing so much. This is a different style of episode for the podcast, and one I’ve been wanting to do more of: sitting down with interesting people who have lived extraordinary lives and letting them tell the stories themselves. Enjoy the conversation. here is the link to buy "Iron Will" https://www.yachtworld.com/yacht/2006-custom-sprague-9996693/

I’ve spent years living and traveling on boats, but lately I’ve been back on the road in the RV — and it got me thinking: which lifestyle is actually better? In this podcast, I compare RV life vs boat life from someone who has lived both. We talk about the cost, maintenance, freedom, comfort, travel, adventure, social life, living with dogs, and all the little things that make each lifestyle amazing — and frustrating. RV life is definitely easier in a lot of ways, but does boat life offer something you just can’t get on land? And the bigger question… could I ever give up boat life for RV life? Let me know in the comments: if you could choose only one, would you live on an RV or a boat?

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 today than it was for previous generations, why fewer people are willing to risk everything, and whether the world has simply run out of places where your past does not define your future. I also share a story from my own family history about an ancestor who, according to the story passed down through my family, was the thirteenth son of an English lord. With little chance of inheriting anything, he left England for the New World to build a life of his own. We discuss the influence of the frontier on American ambition and entrepreneurship, the uncomfortable truth that these lands were never actually empty, and whether technology, space, artificial intelligence, international living, and online businesses have become the new frontiers. Maybe there are no truly undiscovered places left. But perhaps the biggest frontier has always been the decision to walk away from the life you were given and attempt to create a different one. Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles

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 explain what happened from my perspective. I also give an update on my health, future cruising plans, the Great Loop, the Great Lakes, Maverick, and several other questions submitted by viewers. There are a few major questions about Maverick and my discussions with Island Spirit that I’m not ready to answer publicly yet. I did answer them fully in the uncut patron version of this podcast. Become a patron to watch the complete, unedited episode and hear the parts that were removed from the public version. The full 40-minute documentary about the Cape Hatteras incident is also available as a pay-per-view video on my website. Watch the Scary moment my boat almost caught fire and sunk: https://sailingdoodles.com/fire-at-sea/ Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/ Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles