Why I’m Selling My 56-Foot Sailboat

How dangerous is it really to sail around the world? Are pirates something sailors should actually worry about? While sailing through Indonesia, we stopped at a tiny, remote atoll hundreds of miles from civilization. Just as we were preparing to leave, a wooden boat carrying six men headed straight toward us. With only me and two women aboard, we had no idea what they wanted. What happened next was something I'll never forget! In this episode of The Bobby White Podcast, I share the incredible story of that encounter, complete with original footage, and discuss the real dangers of piracy while cruising. I also share the terrifying story of a father and son who were attacked and robbed aboard their catamaran in Brazil, discuss the tragic murder of an American sailing couple in the Caribbean, and give my thoughts on dangerous cruising destinations and whether carrying a gun aboard is a good idea. Is sailing around the world actually dangerous, or is the fear of pirates mostly overblown? Watch the original Sailing Doodles adventure here: https://youtu.be/Q-boTJkn5h0 Formerly The Sailing Doodles Podcast. #BobbyWhitePodcast #SailingDoodles #Pirates #Sailing

I was one of the very first pilots hired by Flydubai back in 2009, and I was there for the airline's very first passenger flight. But after a little over a year flying the Boeing 737 for them, I decided to leave. Following the recent shocking incident involving a Flydubai first officer, I'm sharing my firsthand experience working for the airline, the problems I saw with management and scheduling, and my concerns about pilot hiring standards and background checks. I'll also discuss the major differences between American and international pilot training, why I prefer certain airlines when I travel, and why I believe AI and automation could make the traditional airline pilot career obsolete much sooner than people think. As a former airline and corporate pilot, I've got some strong opinions about where aviation is headed.

Before YouTube, I spent four years living in Nigeria and flying a Gulfstream III all over Africa for a wealthy businessman. In this episode, I tell some of my favorite stories from that time — living in Maiduguri and Abuja, dealing with police bribes, flying across Africa, mechanical problems in the middle of nowhere, bird strikes, armed guards, and some very unusual passengers and destinations. I also tell the story of flying the Prime Minister of Somalia to Libya and unexpectedly finding Muammar Gaddafi waiting for us on the ramp. It was one of the strangest, most interesting chapters of my flying career.

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/