Sailing Doodles Podcast

In this episode of the Sailing Doodles Podcast, I finally sit down with Chloe for a real conversation about her background, where she came from, and how she ended up joining the crew. It’s a fun, honest episode where you really get to know her beyond what you see in the videos… But we also share some important news. Chloe will be leaving Sailing Doodles for now to head home and take care of some medical things. We talk about what’s going on, what this means moving forward, and what’s next. It’s not goodbye forever — just a new chapter. Chekc out her Patreon https://www.patreon.com/chloer

In this episode of the Sailing Doodles Podcast, I’m answering your questions—from the new 525e catamaran build to future sailing plans, life in Thailand, and yes… Chloe. We cover everything from boat systems and upgrades, to where I’m sailing next, to how all of this actually works behind the scenes. Nothing is off limits in this one. Topics include: Status of the new Island Spirit 525e Future sailing plans (Maldives, Australia, beyond) Life and relationships on the road and at sea Boat systems, maintenance, and lessons learned Content, Patreon, YouTube, and how it all works Thanks to everyone who submitted questions—these AMA episodes are some of my favorites to do.

For years I assumed I had another 5–10 years as a content creator before technology really started disrupting things. After seeing how fast AI video is advancing… I’m not so sure anymore. AI can now generate voices, scripts, music, and even realistic video scenes. I recently watched several AI-generated reels and videos that honestly fooled me at first. And the scary part is this technology is improving incredibly fast. In this episode I talk about: • AI-generated videos that fooled me • How fast AI video is improving • Why creators might actually lose this battle • How AI could flood YouTube with unlimited content • Whether real creators will still be able to make a living Even if people prefer real creators, the amount of AI content coming could make it almost impossible to compete. But there may still be one thing AI can’t replicate… real life experiences. So is this the end of creators, or just the next evolution of content creation?

Ever wondered how hard it is to move pets internationally? visit AE Pets https://www.aepetsgo.com In this episode of The Sailing Doodles Podcast, I break down exactly what it took to move my two dogs from the United States all the way to Thailand. There are a lot more steps involved than most people realize — health certificates, government approvals, airline regulations, quarantine rules, and more. To help explain the process, I sit down with James from AE Pets International, the company that handled the logistics of transporting my dogs. We talk about how international pet shipping works, what pet owners need to know before moving abroad, and how professionals coordinate everything from paperwork to flights to make sure pets arrive safely. If you’re planning to travel or relocate overseas with your pets, this episode will give you a behind-the-scenes look at the process and how to make it much easier. Topics we cover: • The paperwork required to ship pets internationally • Health certificates and vaccination requirements • Airline cargo vs passenger transport • What happens when pets land in a new country • Common mistakes pet owners make • How pet shipping companies simplify the process Whether you're moving abroad, sailing around the world, or just curious about how pets travel internationally, this episode will walk you through everything. become a patron! https://www.patreon.com/sailingdoodles

In this episode of The Sailing Doodles Podcast, I dive into one of the biggest decisions I’ve ever made… going all-electric with the new catamaran. Why did I choose an electric propulsion system? How does it compare to boats like Fountaine Pajot’s electric cats? What are the real risks — lightning, reliability, long-term maintenance? And what spares and tools will I be carrying to prepare for worst-case scenarios? Then we pivot into your most asked personal questions… – Will there be rotating crew in Thailand? – What’s happening with Flying Doodles and Emma? – Can I get my pilot’s license back? – Does Chloe ever get tired of keeping her real name private? – And yes… how dating works when you’re constantly moving. We also talk YouTube growth “experts,” long-term life plans, the Bronco, and my favorite episode I’ve ever created. Big changes ahead. Let’s get into it.

In this episode of The Sailing Doodles Podcast, I sit down with Emma — the host of Flying Doodles — to talk about her aviation journey, career path, and what really goes on behind the scenes of the channel. From her flight training and early experiences in the cockpit to where she sees her aviation career heading next, Emma shares stories you haven’t heard before. We also talk about the future of Flying Doodles, upcoming projects, and what excites her most about aviation right now. If you’ve been watching Flying Doodles and wondering who Emma really is and how she got here — this is the episode for you. Make sure you check out @flyingdoodles here: https://www.youtube.com/c/FlyingDoodles/ Let us know in the comments: What should we film next on Flying Doodles? #FlyingDoodles #AviationPodcast #PilotLife #SailingDoodles

In this Ask Me Anything episode, I answer the question everyone keeps asking… Who is actually coming with me to Thailand to pick up the new boat? There’s been a lot of speculation about crew, plans, and what’s happening next — so I finally address it. I also talk about: Whether Chloe is joining me Lauryn? Thailand flotilla details What I actually have planned once I get there The current status of the boat raffle RV updates and the Camping World situation Craziest sailing mistakes I’ve ever seen And how to get hired on a sailboat Big year ahead. New boat. New adventures. Possibly new crew. Let’s get into it.

This one feels surreal to say out loud — the new boat is getting very close to completion. In this update, I share where the build is at, what’s left to finish, and why this moment feels different than anything before. After months (and years) of planning, I’ll be flying to Thailand next month to finally step onboard and start the next chapter. I know a lot of you have been following this journey from the beginning, and I can honestly say… I’m just as excited (and nervous) as you are. Thanks for sticking with me — things are about to get really interesting. 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/

Sailing YouTube looks easier than ever — bigger audiences, better cameras, more success stories. But the reality? It’s harder now than when I started, and most sailing channels don’t even make it past year two. In this episode, I break down why channels really fail — not because they can’t sail, but because they run out of money, burn out, struggle with people, or misunderstand how YouTube actually works today. I talk honestly about how long it took me to break even, living on beans and rice, dealing with burnout that never really goes away, why subscribers matter less than they used to, and why AI might be the biggest challenge creators face next. This isn’t meant to discourage anyone — it’s meant to prepare you. If you’re thinking about starting a sailing channel, or you’ve wondered why so many disappear, this episode is for you.

In this podcast, I answer one of the biggest questions I’ve been getting lately: who’s coming with me to Thailand on the new boat? We talk about the new boat timeline, potential crew lineup, and what this next chapter of Sailing Doodles is really going to look—both on and off camera. I also address questions about Chloe, future appearances, and how I handle bringing new people into the videos while balancing privacy, reality, and the internet’s opinions. We also dive into: Who may be joining the boat in February How crew decisions actually get made Viewer questions about drones, sailing, and life on the water What changes (and what stays the same) with the new boat Big changes ahead—this episode gives you the real story.

A month or so ago, I shared a podcast about the nightmare I was dealing with on my RV — and at the time, I hadn’t even gotten to the worst part yet: needing a full engine overhaul. In this episode, I give a full update on everything that happened afterward, how the situation evolved, and how Camping World ultimately stepped up and made things right. It was a long, stressful process, but in the end they took care of the problem, made me whole, and even got me into a newer and better RV. I believe in being fair and transparent — good or bad — and this episode is about how things actually turned out and why I’m satisfied with the resolution. If you’re an RV owner, considering buying one, or just curious how these situations really get handled behind the scenes, this update is worth listening to.

In this episode, I share my personal thoughts on the tragic aviation accident involving Greg Biffle and his family. I had the opportunity to meet Greg and his wife Kristina about a year and a half ago at Spanish Cay Yacht Club, and they were incredibly kind, welcoming people. This is not an episode about speculation or assigning blame, but rather about acknowledging the human loss, explaining what is currently known, and offering perspective on how unforgiving aviation emergencies can be—especially shortly after takeoff and in marginal weather conditions. Investigations by the Federal Aviation Administration and the National Transportation Safety Board are ongoing, and it will be many months before definitive answers are available. My thoughts and condolences are with everyone affected by this heartbreaking tragedy.

You asked some tough questions, so it’s time to answer them. In this Q&A episode I cover everything from crew changes and relationships, to insurance and the new boat, along with sailing myths, health insurance while cruising, provisioning mistakes, and what’s coming next for Sailing Doodles and the spin-off channel. Nothing scripted, nothing off limits, just honest answers to the questions you’ve been sending in. Thanks to all the patrons and supporters who keep this channel going and help shape these conversations. Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles 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/

Ever wondered what sailing is really like? After years living aboard, crossing oceans, rescuing boats, breaking boats, and teaching new crews how to sail, I’ve heard every sailing myth in the book… and today we’re busting the big ones. In this episode, we break down the 12 most common (and most misleading!) sailing myths that stop people from getting on the water — including the truth about boat costs, storms, sharks, catamaran safety, anchoring, YouTube crew life, and whether you actually need experience before buying a boat. Whether you’re dreaming of cruising, already sailing, or just love the lifestyle, this podcast will give you a real-world look at what sailing is actually like… the good, the bad, and the hilarious. To apply: Send a short introduction video uploaded to YouTube (public or unlisted) and email me the link. Tell me who you are, why you want to join, and what makes you the perfect fit. [email protected] Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles 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/

After many delays, stress, paperwork, and uncertainty… the insurance saga is finally over. As most of you know, the delivery crew had a major mechanical failure last year that led to my boat being totaled. Since then, I’ve been working through the long insurance process behind the scenes. I can’t share specific numbers, terms, or private details because of my NDA — but I can walk you through what the experience was like, what I learned, and how this affects the future of Sailing Doodles. In this episode I cover: What I can legally say about the resolution What this means for the new boat build And what’s next for the channel Thank you to everyone who supported me during this ordeal — the comments, messages, and patience meant more than you know. Time to move forward and get back to sailing! To apply: Send a short introduction video uploaded to YouTube (public or unlisted) and email me the link. Tell me who you are, why you want to join, and what makes you the perfect fit. [email protected] Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles 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/

Ever wonder where everyday expressions like “three sheets to the wind,” “overboard,” “the bitter end,” or even “windfall” actually came from? Turns out, tons of common words in English were invented by sailors, pirates, and old-school sea captains, and today we still use them without even thinking about it. In this episode of the Sailing Doodles Podcast, I break down over 80 everyday words and sayings that all started on ships — from naval terms, pirate slang, emergency commands, rigging language, and old maritime traditions. Some of these are obvious… but most of them will absolutely blow your mind! If you enjoy sailing, history, language, or just fun trivia, this is a super entertaining deep dive into how much of modern English came from life at sea. Fair winds and following seas — and thanks for listening! If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles

What upgrades are actually worth the money on an older sailboat… and which ones you should avoid? In this episode of The Sailing Doodles Podcast, I break down the most valuable upgrades I’ve done across all the boats I’ve owned — from my classic CT-56 to the newer catamarans and charter boats we’ve sailed. I cover which improvements truly make your boat safer, easier to sail, and more enjoyable… and which “fancy” upgrades usually end up being a waste of money. If you’re shopping for an older cruising boat or planning a refit, this episode will save you thousands. Topics Covered Why buying a boat already upgraded is often cheaper Rigging, sails, and critical safety upgrades Ground tackle & anchoring systems worth investing in Autopilots, instruments & navigation upgrades Electrical systems, lithium, solar & charging Refrigeration: why it’s usually a later priority Comfort upgrades: electric winches, watermakers & more What to skip… and what will absolutely transform your cruising About the Channel I’m Bobby from Sailing Doodles. I sail, travel, and document the adventure while running my YouTube channels from around the world — from the Caribbean and the Bahamas to the Mediterranean and beyond. If you enjoy the episode, hit subscribe and check out the sailing raffles, flotillas, and behind-the-scenes content! Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles 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/ Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles

The fans didn’t hold back on this one… In this Q&A episode, I answer YOUR questions about the new catamaran, future sailing plans, past crew, and even a few spicy ones about “hot babes” and babies on board We talk about: • Updates on the new Island Spirit 525e catamaran (Hull #5) • Future cruising plans in Thailand and the Mediterranean • Crew, relationships, and how the channel has evolved • Life as a full-time liveaboard and YouTuber • Gear, filming setups, and how the dogs handle land life Thanks to everyone who submitted questions — I read as many as I could! Watch next: [link to related podcast or vlog] Join the Sailing Doodles community: Patreon / Podia links Follow along on Instagram: @SailingDoodles #SailingDoodles #Podcast #QandA #SailingLife #BoatLife Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles 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/ Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles

I just bought a brand-new RV… and it didn’t even make it off the lot before breaking down. Within minutes, the engine started smoking and I quickly realized the EGR cooler had failed, dumping coolant straight into the exhaust. In this episode of The Sailing Doodles Podcast, I talk about what happened, how I diagnosed the issue, and what comes next. The dealer says they’ll cover the repair — but we’ll see what really happens. I’ll share what I’ve learned from years of owning boats, planes, and RVs about mechanical failures, warranty claims, and how to handle breakdowns the smart way. Topics: How to spot EGR cooler failure symptoms What happens when coolant enters the exhaust Towing and dealer negotiations Lessons learned when buying new rigs Listen on YouTube, Spotify, or anywhere you get your podcasts. #RVBrokeDown #RVPurchase #EGRcooler #SailingDoodlesPodcast Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles 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/ Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles

In this episode, I dive into how sailors and cruisers deal with one of the biggest threats on the ocean — hurricanes. Fifty years ago, crossing an ocean meant hoping you didn’t run into a storm. There was no internet, no satellite tracking, and little warning. Today, we carry a weather computer in our pocket, with live hurricane data, Starlink connectivity, and routing tools that can literally save lives. We’ll talk about: How hurricane forecasting has changed in just a few decades The role of Starlink and modern weather apps at sea What the “hurricane box” is — and why insurance won’t cover you inside it How cruisers migrate north and south each year to stay safe Where sailors ride out storms (the famous “hurricane holes”) The truth about insurance loopholes and “named storm” clauses Real stories, lessons learned, and what it’s like to live with hurricane season as a full-time cruiser If you’ve ever wondered how modern sailors dodge hurricanes — or how it was done before the digital age — this episode will blow your mind. Leave a comment: Where do you go during hurricane season? Subscribe for more real-life sailing stories, tech talk, and behind-the-scenes of the cruising lifestyle. #SailingDoodles #HurricaneSeason #SailingPodcast #CruisingLife #StarlinkAtSea #SailingTips

A Queensland superyacht agent was offered $300,000 for a “simple” job — help two divers enter Australia. Days later, one diver was dead, another had vanished, and 100 kilos of cocaine were floating in Newcastle Harbor. In this episode, Captain Bobby White of The Sailing Doodles Podcast breaks down the true story of James Blake Blee — how financial desperation led to a deadly smuggling plot, what “parasite smuggling” really is, and why this growing underwater drug tactic is spreading around the world. All details sourced from court reports, News.com.au, ABC Australia, and VICE News investigations. Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles 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/ To apply: Send a short introduction video uploaded to YouTube (public or unlisted) and email me the link. Tell me who you are, why you want to join, and what makes you the perfect fit. [email protected] Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles

A U.S.-flagged motor yacht was raided by Bahamian authorities in Bimini after a tip-off — and what they found shocked everyone. Ten people were arrested, including the crew, and officers seized a cache of weapons, ammunition, and cash. In this episode, Captain Bobby White of Sailing Doodles breaks down the facts, shows footage from the local news, takes a look at the yacht’s charter listing, and shares his honest opinions about carrying weapons onboard and the risks every cruiser faces when crossing borders. I’m not a lawyer — this is my perspective as a captain who’s checked in at Bimini many times. Always verify local laws before you travel. Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles 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/ To apply: Send a short introduction video uploaded to YouTube (public or unlisted) and email me the link. Tell me who you are, why you want to join, and what makes you the perfect fit. [email protected] Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles

This week’s Sailing Doodles Podcast gets personal. Viewers submitted hundreds of questions — and of course, the most common one was about Laura. Are Laura and I getting back together? What really happened behind the scenes at the Annapolis Boat Show? And how does Miss Lone Star fit into all this? I also answer your questions about the new catamaran, future flotillas, the boat raffle, and what’s next for Sailing Doodles in 2026. Drop your next questions in the comments for the next Q&A episode! Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles 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/ To apply: Send a short introduction video uploaded to YouTube (public or unlisted) and email me the link. Tell me who you are, why you want to join, and what makes you the perfect fit. [email protected] Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles

This might be the biggest announcement I’ve ever made. I’m looking for two people — ideally a couple — to come sail with me in Thailand this February for four months. You don’t need sailing or editing experience. I’ll teach you how to sail, how to film, and how to create a YouTube channel like Sailing Doodles. The goal? To train the next generation of creators and help them launch their own sailing channel when the journey’s done. In this episode, I explain what I’m looking for, what the experience will be like, and how to apply. To apply: Send a short introduction video uploaded to YouTube (public or unlisted) and email me the link. Tell me who you are, why you want to join, and what makes you the perfect fit. [email protected] Patreon members will get to watch the submissions and help me decide who joins the crew. If you want to be part of the process, join here: https://www.patreon.com/sailingdoodles This is your chance to change your life — to learn, explore, and start your own adventure.

At the Annapolis Boat Show, Bobby sits down with Amanda and Maryline from Current Yachts, a new brokerage that’s shaking up the traditional 10% commission model. Instead of sky-high broker fees, they’re offering a flat-fee, transparent system — just $1,500 to list your boat and à-la-carte options for everything else. We dive into why they believe the old system is broken, how they’re making boat buying and selling fairer, and what this means for the future of yacht sales. If you’ve ever thought about selling your boat — or buying one — you won’t want to miss this conversation. Check out Current Yachts https://www.currentyachts.com This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles

Fan-favorite Laura from Sailing Doodles Seasons 2 & 3 is back! She joined me at the Annapolis Boat Show with her two young kids, and things got a little… chaotic. We catch up on what Laura’s been up to since her sailing days, talk about motherhood, life after the show, and the possibility of getting back on the water. This one’s totally “wheels off” — her 14-month-old demanded plenty of attention (and snacks), interrupted mid-sentence, and even forced an unexpected break for feeding time. It’s messy, real, and absolutely hilarious. If you’ve missed Laura’s energy, laughter, and down-to-earth honesty — this episode’s for you! Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles 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/

What started as one man’s dream to sail the world has grown into one of the most ambitious and inspiring sailing projects on YouTube. In this episode of The Sailing Doodles Podcast, I sit down with Nate and Amy from Expedition Drenched to uncover how it all began — from filming underwater expeditions to building a worldwide nonprofit that protects the oceans. We talk about: How Nate left everything behind to chase a life at sea The early struggles of creating a sailing show with a bigger purpose What makes Expedition Drenched so different from other sailing channels How their team balances adventure, filmmaking, and marine conservation If you love sailing, filmmaking, or stories of people chasing meaning over money — this is a must-watch. #SailingDoodles #ExpeditionDrenched #SailingPodcast #OceanConservation Check out Expedition Drenched on Youtube: https://www.youtube.com/@ExpeditionDrenched

Sailing the Caribbean has always been a dream — but is it getting riskier? Between rising fees in the Bahamas, U.S. drug-interdiction ops near Venezuela, and shifting maritime laws, we dive into whether the Caribbean is still the paradise sailors imagine. In this Q&A episode, I answer fan questions on: Safety in the Caribbean today Rising costs in the Bahamas & alternatives like Cuba and the BVIs Planning & paperwork for international cruising Boat ownership, chartering, and insurance lessons Life aboard with crew, pets, and future sailing plans Drop your thoughts in the comments — would YOU still sail the Caribbean right now? Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles 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/ get tickets for the Annapolis Show: https://annapolisboatshows.ticketspice.com/annapolis-sailboat-show?t=SailingDoodles

In this special episode, I’m sharing my full life story — from my childhood sailing a Sunfish on my grandparents’ lake, to my aviation career flying Gulfstreams for celebrities, to the stroke that ended my flying days, and how that ultimately led to creating Sailing Doodles. It’s been a wild ride: flying rockstars around the world, living in Nigeria and Dubai, surviving a medical crisis, and then finally selling everything to chase the dream of sailing full time. I’ll take you through the twists, setbacks, and adventures that brought me here today. If you’ve ever wondered how Sailing Doodles started — this is the story behind it all.

Ever dreamed of selling it all and retiring to sail the world? In this episode of The Sailing Doodles Podcast, Bobby breaks down what it really takes to make that dream happen. From health and fitness (because sailing isn’t a spectator sport), to money and income streams, to choosing the right boat and lifestyle — we cover it all. Whether you’re 55 and planning ahead or 67 and wondering if it’s too late, this episode gives you the honest truth about the realities of retiring at sea. Topics include: Why your health matters more than your bank account How much money you really need to cruise full-time Passive vs. non-passive income while sailing Why your boat should be paid off before you cast off The mental and lifestyle adjustments that make or break retirement cruising Subscribe for more stories, tips, and real talk about life on the water!

t’s time for another viewer Q&A podcast! In this episode, I answer your most popular questions about life on Nauti Dogs, the upcoming new catamaran, what’s happening with the crew, and even some personal stuff you’ve all been curious about. We cover everything from: Plans for raffling off Nauti Dogs Who might join as the first crew on the new boat My thoughts on flotillas, the Great Lakes, and future destinations Tech and maintenance questions — chart plotters, radar, twin-engine sync Personal topics like crew relationships, family, and even those AI “net worth” videos Thanks to everyone who submitted questions on YouTube, Patreon, and Podia — you make these episodes possible! If you want to submit your own questions for future podcasts, join our community here: [link to Patreon/Podia] get tickets for the Annapolis Show: https://annapolisboatshows.ticketspice.com/annapolis-sailboat-show?t=SailingDoodles Make an appointment to see 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/

Think the ocean is lawless? Think again. In this episode we dive into some of the quirkiest maritime laws that still affect sailors today — from the Coast Guard’s power to board your boat anytime without probable cause, to the myth of 33% salvage rewards, to fines for flying the wrong or tattered flag, bizarre anchoring restrictions, and even odd crew contract rules. Topics covered: Coast Guard boarding authority (Revenue Act roots & Prohibition era) Salvage rights & the truth behind the 33% myth Courtesy flag fines & quirky traditions Anchoring bans, seagrass zones, and “pay-to-anchor” politics Crew contracts, Bible laws, and desertion rights Have you ever been boarded, fined, or tangled up in a weird maritime rule? Share your story in the comments — I’d love to hear it. get tickets for the Annapolis Show: https://annapolisboatshows.ticketspice.com/annapolis-sailboat-show?t=SailingDoodles Make an appointment to see 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/

It’s time for another Q&A podcast with questions straight from our amazing Patrons and YouTube Members! In this episode, I cover: The biggest sailing mistakes I’ve made (and what I learned) Updates on the new catamaran in Thailand and what’s next for Sailing Doodles Thoughts on circumnavigation, the Pacific vs. Caribbean, and charter advice Crew questions — who’s joining, what happened with past crew, and Aubrey’s future plans The latest on insurance, gear, and electric boat tech Plus stories about the dogs, Burning Man, and life on the water Huge thanks to our supporters who submitted these questions — if you’d like to be part of the next Q&A, join us on Patreon or as a YouTube Member. Don’t forget to subscribe for more sailing adventures, podcasts, and behind-the-scenes updates! get tickets for the Annapolis Show: https://annapolisboatshows.ticketspice.com/annapolis-sailboat-show?t=SailingDoodles Make an appointment to see 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/

In this episode of The Sailing Doodles Podcast, I sit down with Lauryn from Lost Lauryn to talk about her life of adventure. She’s built a following with her motorcycle channel, traveling on two wheels and sharing her journey, and recently she joined me on a sailing trip at sea. We dive into: How she started her motorcycle channel and what inspires her adventures The challenges (and rewards) of documenting life on the road Her experience sailing with me and what surprised her most about life on the water What’s next for her in both motorcycles and sailing It’s a fun conversation about chasing freedom, creating content, and living life off the beaten path. Don’t forget to subscribe for more sailing stories, travel adventures, and conversations with fascinating guests. This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles

In this episode of The Sailing Doodles Podcast, I sit down with fellow YouTuber Auburey from Sailing Miss Lone Star while we’re in Greece chartering a catamaran together. We talk about: Her journey into sailing and YouTube What it’s like sailing with an 11-month-old baby on board Our first time sailing together from Athens to Aegina The ups and downs of life as full-time sailing creators It’s a fun and honest conversation about the realities of sailing, motherhood at sea, and the adventures that come with chasing this lifestyle. Make sure to check out Auburey’s channel Sailing Miss Lone Star and subscribe for more podcasts with sailors, cruisers, and adventurers from around the world. Want to charter a boat in Greece! Check out Istion and get 10% off with out discount code "DOODLES10" Head over to: https://bit.ly/DOODLES10 This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles

In this episode, I take a moment to address some recent negativity from former crewmates. While I won’t name anyone or speak ill of them, I wanted to share my feelings of disappointment and how I’m choosing to respond with positivity. I also want to thank everyone who’s sailed with me over the years, and I’m honored by the memories we’ve shared. On a brighter note, former crewmate Sydney sent in a beautiful video sharing her appreciation for her time on board. Tune in for a mix of gratitude, reflection, and a little behind-the-scenes honesty. Let Sydney whip you into shape! https://future.co/?code=sydney_p&rdrorigin=%2Fsydney_p 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/ Here is the link for 5% off Total Boat: https://www.totalboat.com/?sca_ref=7873710.M07fS3H4Xu

From lightning strikes and engine failure to fires and man overboard situations—this episode dives deep into the scariest things that can happen on a boat. I’ve lived through a few of these, and others are every sailor’s nightmare. But fear not—this episode isn’t just about horror stories. We break down how often these emergencies happen and give real-world tips on how to prevent or survive each one. If you’ve got a wild sea story, drop it in the comments—I might feature it in a future episode! Watch the full video of my scary moment catching fire around Cape hatteras. https://www.sailingdoodles.com/fire-at-sea/ Check out Electrical Marine in Thailand https://www.electrical-marine.com Protect your boat with SerTec: https://www.sertecmarine.com/en/

In this episode of The Sailing Doodles Podcast, I’m giving you an exclusive first look at Hull #3 of my brand-new catamaran! It’s currently on a ship en route to Annapolis, and I couldn’t be more excited to finally share the journey with you. This is the boat that will take Sailing Doodles to the next level—literally across oceans—and you’re getting the inside scoop before anyone else. Come see it in person! I’ll be at the Annapolis Boat Show, and you’re invited to come check out the new boat for yourself. It’s your chance to step aboard, meet the team, and get a feel for the boat you’ll be seeing a lot of in upcoming videos. Annapolis Boat Show — Be There! Let me know in the comments if you’re coming! 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

Everyone sees the bikinis, sunsets, and crystal-clear water… but what does it really take to film a successful sailing YouTube channel? In this episode of the Sailing Doodles Podcast, I break down what goes on behind the scenes—from the long hours editing and filming, to the planning, crew management, and sacrifices it takes to stay consistent. I’ll also share why you have to treat this like a full-time job if you want to succeed, how many videos it actually takes to build momentum, and answer some of your most asked questions about gear, crew, burnout, and bloopers. Want to start your own channel? Start here. This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles 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/ Here is the link for 5% off Total Boat: https://www.totalboat.com/?sca_ref=7873710.M07fS3H4Xu

After years of sailing with dozens of amazing crew members, I finally answer one of the most asked questions — Who was my favorite? From wild adventures to quiet sunsets, I look back on everyone who’s joined me aboard and share my thoughts on what made each of them special. Plus, I answer a bunch more of your fan questions — about relationships, cruising costs, boat life, and what I’d do if I weren’t doing this at all. Chime in down in the comments — who was your favorite crew member to watch? This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles 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/ Here is the link for 5% off Total Boat: https://www.totalboat.com/?sca_ref=7873710.M07fS3H4Xu

The Bahamas just hiked their cruising permit fees—and boaters are not happy. In this episode of The Sailing Doodles Podcast, we break down the old vs. new fees, what’s changed, and how it's impacting the cruising community. Are these changes smart revenue moves or a huge mistake that could cost the Bahamas its sailing tourism industry? I’ll share the facts, the fallout, and what this means for cruisers of all types. Check out ArunaLight and use code "doodles10" for 10% off! https://www.arunalight.com This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ Island Spirit and Inspired Yachting contact Phillip Winter [email protected] 727-648-0044 https://www.inspiredyachting.com/ Here is the link for 5% off Total Boat: https://www.totalboat.com/?sca_ref=7873710.M07fS3H4Xu

What happens when Deadpool and Wolverine dive into the world of high-speed sailing?

In this episode of the Sailing Doodles Podcast, I answer the top questions submitted by our fans and patrons. From frustrating insurance delays on the Island Spirit 525 to dating challenges while living full-time on a sailboat — nothing’s off limits. We talk: Insurance delays and the new catamaran timeline What it’s really like choosing crew — and what I look for Dating while sailing The truth about living aboard with dogs Tech talk: hydrogenerators, drones, and boat systems Plus… the biggest waves and sharks I’ve ever seen! If you've ever wondered what goes on behind the scenes of Sailing Doodles, this episode dives deep. Available on YouTube, Spotify, and Apple Podcasts. 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/

Ever wondered how much it really costs to live and cruise on a sailboat? In this episode, Bobby breaks down the actual monthly expenses of full-time boat life—from marina fees and diesel costs to food, maintenance, and those sneaky hidden costs no one warns you about. Whether you're planning to set sail soon or just dreaming of escaping the 9-to-5, this episode gives you a realistic look at the dollars behind the dream. Chapters include: Monthly cruising budget breakdown Unexpected boat expenses Cost-saving tips from years at sea Is cruising really cheaper than land life? This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles

In this episode of the Sailing Doodles Podcast, I sit down with our newest crew member, Jennifer Brown (@jenniferbrownakajb) — a model, actress, and influencer who's traded the runway for the rigging. We talk about her first impressions of life aboard, her background in entertainment, and what it’s like transitioning into the world of sailing. From sunsets to salty decks, Jennifer shares what she’s loving (and learning) about cruising life. Don’t miss this fun conversation about adventure, change, and chasing freedom on the water! This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ Island Spirit and Inspired Yachting contact Phillip Winter [email protected] 727-648-0044 https://www.inspiredyachting.com/ Here is the link for 5% off Total Boat: https://www.totalboat.com/?sca_ref=7873710.M07fS3H4Xu

In this special Q&A episode of the Sailing Doodles Podcast, I’m answering your best questions from Patreon, Podia, and YouTube Members! From what really happened with former crew like Lauryn and Amanda, to whether my boat is still worth fixing… nothing is off the table. We’re diving into: My relationship with past and current crew Behind-the-scenes costs of Sailing Doodles Insurance battles and boat maintenance headaches Why the Chesapeake? Why not the Med? What I’d do if YouTube disappeared tomorrow The future of Nauti Dogs, Maverick #2, and life onboard Thanks to everyone who submitted thoughtful (and juicy!) questions. If you want yours featured in the next one, join the community on Podia, Patreon, or YouTube Memberships! This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ Island Spirit and Inspired Yachting contact Phillip Winter [email protected] 727-648-0044 https://www.inspiredyachting.com/ Here is the link for 5% off Total Boat: https://www.totalboat.com/?sca_ref=7873710.M07fS3H4Xu

Wondering where the best cruising grounds in the world really are? In this episode of The Sailing Doodles Podcast, I break down the pros and cons of sailing in every major region — from the East and West Coast of the U.S., to the Bahamas, Caribbean, Mediterranean, Indian Ocean, Asia, Australia, and the far reaches of Polynesia and the South Pacific. I’ll walk you through: What each region offers (and what to watch out for) Where to go for remote exploration vs. luxury marinas The truth about safety, weather, and bureaucracy My personal favorite sailing destinations Plus, I’ll explain why you don’t hear much about cruising in places like Africa, South America, and China. Whether you’re dreaming of your first bluewater voyage or planning your next big crossing, this episode will help you figure out where in the world YOU should be sailing. Got your own top spot? Drop a comment and let me know where you'd go next. Bobby Host, The Sailing Doodles Podcast 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/ This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy https://sailingdoodles.podia.com/sailing-doodles-course-community or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join or join our Patreon http://www.patreon.com/sailingdoodles Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: Precision Sails: https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles Highfield Boats: https://www.highfieldboats.com/ Island Spirit and Inspired Yachting contact Phillip Winter [email protected] 727-648-0044 https://www.inspiredyachting.com/ Here is the link for 5% off Total Boat: https://www.totalboat.com/?sca_ref=7873710.M07fS3H4Xu #SailingLife #NewBoat #SailingDoodles #IslandSpirit #CatamaranLife