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. cruise@sailingdoodles.com 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/sailingdoodlesEnter 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 resolutionsWhat this means for the new boat buildAnd what’s next for the channelThank 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. cruise@sailingdoodles.comPatreon 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/sailingdoodlesEnter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodlesWant 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 CoveredWhy buying a boat already upgraded is often cheaperRigging, sails, and critical safety upgradesGround tackle & anchoring systems worth investing inAutopilots, instruments & navigation upgradesElectrical systems, lithium, solar & chargingRefrigeration: why it’s usually a later priorityComfort upgrades: electric winches, watermakers & moreWhat to skip… and what will absolutely transform your cruisingAbout the ChannelI’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-doodlesWant 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 lifeThanks 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 linksFollow along on Instagram: @SailingDoodles#SailingDoodles #Podcast #QandA #SailingLife #BoatLifeEnter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodlesWant 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 symptomsWhat happens when coolant enters the exhaustTowing and dealer negotiationsLessons learned when buying new rigsListen on YouTube, Spotify, or anywhere you get your podcasts.#RVBrokeDown #RVPurchase #EGRcooler #SailingDoodlesPodcastEnter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodlesWant 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 decadesThe role of Starlink and modern weather apps at seaWhat the “hurricane box” is — and why insurance won’t cover you inside it How cruisers migrate north and south each year to stay safeWhere sailors ride out storms (the famous “hurricane holes”)The truth about insurance loopholes and “named storm” clausesReal stories, lessons learned, and what it’s like to live with hurricane season as a full-time cruiserIf 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-doodlesWant 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. cruise@sailingdoodles.comPatreon 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-doodlesWant 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. cruise@sailingdoodles.comPatreon 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-doodlesWant 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. cruise@sailingdoodles.comPatreon 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. cruise@sailingdoodles.comPatreon 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/sailingdoodlesThis 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 Yachtshttps://www.currentyachts.comThis channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navyhttps://sailingdoodles.podia.com/sailing-doodles-course-communityor become a channel memberhttps://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/joinor join our Patreonhttp://www.patreon.com/sailingdoodlesDonate Via Paypal to helphttp://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-doodlesWant 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 seaThe early struggles of creating a sailing show with a bigger purposeWhat makes Expedition Drenched so different from other sailing channelsHow their team balances adventure, filmmaking, and marine conservationIf you love sailing, filmmaking, or stories of people chasing meaning over money — this is a must-watch.#SailingDoodles #ExpeditionDrenched #SailingPodcast #OceanConservationCheck 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 todayRising costs in the Bahamas & alternatives like Cuba and the BVIsPlanning & paperwork for international cruisingBoat ownership, chartering, and insurance lessonsLife aboard with crew, pets, and future sailing plansDrop 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-doodlesWant 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 accountHow much money you really need to cruise full-timePassive vs. non-passive income while sailingWhy your boat should be paid off before you cast offThe mental and lifestyle adjustments that make or break retirement cruisingSubscribe 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=SailingDoodlesMake 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/