Sailing Doodles Podcast

Latest Episodes:

My New Yacht Has Some Problems—Here’s the Full Story Jul 26, 2026

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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

What Kind of Boat Should I Buy Next? Jul 20, 2026

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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

I Was Wrong... Here's the Better Plan Jul 16, 2026

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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

Why Does My Crew Keep Leaving? Jul 15, 2026

Show notes

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

I'm Buying YOU a Yacht? Jul 13, 2026

Show notes

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

Getting a Motor Yacht Instead? Jul 08, 2026

Show notes

In this episode, I talk through a big realization about the future of Sailing Doodles: because of location, weather, and cruising seasons, I may only be able to film on my new catamaran about four months a year. That creates a real problem. If I want to keep making consistent boat content, I may need a second boat. So I’m thinking about buying a smaller motor yacht to keep in Florida and use for cruising the Bahamas, and maybe even doing parts of the Great Loop. I go through the different types of boats I’m considering, what makes sense for the channel, what fits the budget, diesel vs gas, speed vs efficiency, and whether a motor yacht could be the right move for the next chapter. Is this a smart backup plan, or am I just trying to talk myself into buying another boat?

Stop Waiting Until You’re Ready Jun 24, 2026

Show notes

Most people have a dream. Maybe it’s sailing around the world, building a cabin in the mountains, starting a farm, opening a business, moving overseas, or just walking away from a life that looks successful on paper but doesn’t actually make you happy. But most people never do it. Not because the dream is impossible, but because they keep waiting until they’re ready. In this episode, I talk about why I believe you have to set a date, prepare as best you can, and then go. My dream was sailing around the world on a yacht, but this isn’t just about sailing. It’s about risk, freedom, time, work, and the trap of waiting for the perfect moment. I also talk about leaving a good career, the idea of “no risk, no reward,” why doing nothing is also a risk, and why chasing the dream might not work out exactly how you planned — but that doesn’t mean it wasn’t worth doing. You can always get another job. You can’t always get another life. 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

The Questions I’ve Been Avoiding… Health, Olivia & What Happens Next Jun 22, 2026

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In this episode, I’m answering your questions from Patreon, YouTube members, and the Sailing Doodles app. We start with the big one: my recent health scare, the blood clots and thrombosis, whether it could be connected to my past stroke, how medical care has been overseas, and what recovery might look like from here. Then we get into the questions everyone always wants answered: What’s going on with Olivia? Is she coming back to the boat? What happened with the Brazilian girl? Will Chloe or Sailing Miss Lone Star return? I also talk about the dogs, the future of the new Island Spirit 525e, what the delivery crew thought of the boat, the electrical and solar questions, the damaged old hull, possible cruising plans, the Med, the Pacific, RV travel, Burning Man, and what’s next for Sailing Doodles. Thanks for all the questions, support, and well wishes. It has been a strange and stressful chapter, but I’m doing my best to stay positive and figure out the path forward. 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

Is This the End of Sailing Doodles As I Know It? Jun 19, 2026

Show notes

After a big health scare, I’ve had to ask myself some hard questions about the future of Sailing Doodles. I just bought my dream yacht, but now I’m dealing with blood clots and thrombosis in major abdominal veins, and I still don’t have all the answers about what caused it or what the long-term prognosis looks like. For a while, there was even concern it could be cancer, which thankfully seems to have been ruled out. In this episode, I talk honestly about what this could mean for my future: whether I can keep sailing long term, what happens to the new yacht if my health changes, whether I’d sell the boat, hire crew, slow down, or pivot the channel completely. I also talk about what retirement might actually look like, whether I regret buying the boat right before this happened, and what happens to the dogs, the crew, the travel plans, and Sailing Doodles as a whole. This one is personal. I don’t have all the answers yet, but this scare has definitely changed how I think about life, health, travel, and the future of the channel. Thanks for watching and for all the support. 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

My Health Scare: Cancer Fears, Blood Clots, and What Happens Next Jun 16, 2026

Show notes

In this episode, I talk about the medical issue that suddenly interrupted my life and my plans for Sailing Doodles. It started with abdominal pain that I thought might be something minor, but after hospital visits, scans, and more tests, doctors found inflammation around my pancreas and blood clots in the portal vein. For a short time, there was a real fear that it could be pancreatic cancer, which was obviously terrifying. Right now, I’m still waiting on a proper diagnosis. It could be something autoimmune, it could be related to pancreatitis, or it could be something else entirely. I’m on blood thinners, getting more testing done, and trying to understand what this means for my future. I also talk about what this could mean for Sailing Doodles, cruising plans, the new boat, and how something like this makes you rethink everything pretty quickly. This is a more personal episode, but I wanted to be honest about where things stand and what I’m dealing with. 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

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