From Viewer to Crew — I’m Looking for the Next Sailing Doodles

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/