Relationships, Insurance & the New Boat - Ask Me Anything

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