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

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 limitations, and some of the other complications that have interrupted our cruising through Thailand. I explain what happened, what the technicians and builder have done to investigate the problems, and why the generator and battery systems are so important on a yacht designed around electric propulsion. This isn’t meant to attack anyone or declare the entire concept a failure. New boats often have issues, and this yacht uses relatively new and complex technology. I simply want to be transparent with the audience about the good, the bad, and the decisions still ahead. Do we continue improving the hybrid system, make major changes, or consider a more conventional setup? At this point, I’m keeping an open mind. 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

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 cruising? I discuss the features, size, speed, dinghy setup, and practical limitations I would consider before buying. I also answer questions about whether I would collaborate with high-performance powerboat channels, meeting up with other content creators while traveling, and how Cougar and Merlin react to the constant stream of new people joining the boat. Thanks to everyone who submitted questions. Let me know what boat you think would make the best next chapter for Sailing Doodles. 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

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 considering. We dive into whole-boat memberships vs. cabin memberships, pricing, charter economics, premium weeks, refundable deposits, and how this idea might actually become a real business. I still don't know if this will ever happen, but it's already a much better idea because of your feedback. As always, I'd love to hear what you think. Would you join something like this? What would you change? Here is Sam's Blog post: https://sveoti.net/an-open-letter-to-bob-white-sailing-doodles-buying-a-yacht-for-you/ 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 patron Q&A podcast, I answer some of the most common—and most interesting—questions viewers have been asking. I talk about what happened with recent crew members, how I find people to join the boat, the couple who were supposed to launch a Sailing Doodles spin-off channel, whether I’m in a relationship, my changing thoughts about Thailand, plans for the new catamaran, the Mediterranean, the flotilla, and whether I’m seriously considering buying a motor yacht and doing the Great Loop. I also tell a disturbing offshore story about a friend who hired a delivery captain to sail his yacht from the Mediterranean to the Caribbean. In the middle of the Atlantic, the captain suffered a serious mental-health crisis and threatened to jump overboard. My friend had to change course and divert the yacht to the Azores so the captain could safely get ashore and receive help. It raises an important question: what do you do when someone panics, becomes unstable, or simply cannot handle being at sea—with nowhere nearby to get off the boat? Thanks to all the patrons and viewers who submitted questions. 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

What if there was a better way to own a luxury yacht? I've been working on a business idea that I honestly can't decide is brilliant... or completely crazy. Imagine having access to a $1.4 million sailing catamaran that cruises the Mediterranean, Caribbean, Thailand and beyond, without having to buy the whole boat yourself. In this episode I walk through the concept, the numbers, the challenges, and the biggest objections I've already heard. Most importantly, I want YOUR feedback. Would you join something like this? What would make you say yes... and what would make you run away? Leave your thoughts in the comments. Your feedback may completely change this idea. Fill out the survey if you want to go in on this with me! https://docs.google.com/forms/d/e/1FAIpQLSf5cP4pI-etL7w761rhN6DqTA81sLEbRsI0KTpkF3Jhf31-kg/viewform?usp=dialog 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 #SailingDoodle