Regrets, Romance & Refit: Sailing Doodles Unfiltered

In this special Q&A episode, Bobby answers the questions YOU asked — from the biggest mistakes he’s made at sea to the future of Sailing Doodles, what really happened with Amanda, and what it’s like owning the same classic yacht twice. He also tackles topics like finding crew, dealing with black water, his favorite sailing regions, the future of the channel, and even what dogs and Starlink have in common. Whether you’re a long-time viewer or just discovering Sailing Doodles, this episode is packed with behind-the-scenes insight, sailing wisdom, and a few laughs. 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

Living the dream on a sailboat or trawler? It’s not just turquoise water and sundowners—there’s a lot of behind-the-scenes maintenance to keep things running smoothly. In this episode of the Sailing Doodles Podcast, we dive into the day-to-day, weekly, and seasonal upkeep every cruiser needs to manage, whether you're crossing oceans or island hopping. We cover Daily checks and troubleshooting Engine, electrical, and rigging upkeep Hull cleaning and anti-fouling tips Tools and spares you should never cruise without Budgeting and when to haul out Tips to stay ahead of breakdowns while off-grid Whether you’re a new boat owner or a salty vet, this episode will help you stay one step ahead of your boat’s needs. Available wherever you get your podcasts or watch on YouTube.

In this episode, I dive into the realities of owning a boat — the good, the bad, and the expensive. I talk about buying back my old CT, what went wrong the first time, and whether it was actually a smart move financially. I also cover the latest upgrades onboard, including my full solar and lithium setup, and whether it’s powerful enough to run the A/C while at anchor. Plus, I share my thoughts on gas vs. electric engines, insurance headaches, bow thruster repairs, and how I’m prepping for my next catamaran. If you’re thinking about owning a cruising boat — or just want to hear the behind-the-scenes of my boating journey — this one’s for you. 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 deep-dive episode of The Sailing Doodles Podcast, we unpack how the sweeping new U.S. tariffs and turbulent global economic conditions are shaking up the sailboat and yacht industry. From massive increases on import duties—jumping from 1.5% to as high as 54%—to buyer behavior shifts and industry-wide production slowdowns, we cover it all. How these tariffs affect popular brands like Beneteau, Lagoon, Ocean Alexander, and more Why U.S.-built yachts are suddenly more attractive than ever How European and Asian manufacturers are reacting—and adapting The impact on both sailboats and motor yachts What it all means for you if you're buying, selling, or just watching the market Whether you're a full-time cruiser, a dreamer in the research phase, or just trying to make sense of what’s happening in the boating world—this episode breaks it all down in a casual, informative way. Subscribe for more sailing insights, market updates, and boat life stories every week. Drop your thoughts or questions in the comments below—how are these changes affecting your boating plans? #SailingDoodles #YachtMarket2025 #BoatBuying #Tariffs #SailingPodcast #SailboatLife #MarineIndustry Blog Post from SV Eoti & Sam Liles: https://sveoti.net/how-high-tariffs-could-drown-the-mid-tier-yachting-world-and-leave-american-cruisers-stranded/ 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/

In this episode of the Sailing Doodles Podcast, we break down what kind of sailboat you can expect to buy at four very different price points: $10,000, $100,000, $500,000, and $1 million. Whether you're dreaming of a cheap fixer-upper, a bluewater cruiser, a luxury catamaran, or something in between, we explore the features, trade-offs, and realities of buying a boat in each bracket. I share real-world examples, ownership tips, and how each tier fits different sailing lifestyles—from weekend warriors to full-time liveaboards. Grab a drink, tune in, and let’s go yacht shopping—from dirt cheap to dreamboat. 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/

Hey everyone – in this Q&A episode, I’m diving into your most-asked questions about sailing life, crew dynamics, future travel plans, relationships, and of course, the pups. We’ll cover everything from: The recent Bahamas travel advisory and onboard safety protocols Amanda, Lauryn, McKenzie... and the real crew drama My thoughts on switching it up with a trawler and the Great Loop Boat costs, upgrades, regrets, and plans for Island Spirit Hull #5 How being a pilot prepared me for life at sea The dogs’ life aboard and how big they’ll get Highs, lows, and what’s really going on behind the scenes Thanks for sending in so many great questions. If I missed yours, drop it in the comments and I’ll catch it next round! Behind-the-scenes and extras: https://sailingdoodles.podia.com

In this episode of the Sailing Doodles Podcast, we dive into the tragic sinking of the Sinbad submarine off the coast of Egypt—what happened, why it matters, and the chilling details. Then we break down all the latest changes in Florida’s boating laws for 2025, and what you need to know if you’re cruising or living aboard in the Sunshine State. Don’t forget to like, comment, and subscribe for more maritime news and sailing adventures!

In this special episode of the Sailing Doodles Podcast, my crew, McKenzie and Clarice, turn the tables and put me in the hot seat! They ask the hard questions about what it's REALLY like to have them onboard, and I share my unfiltered thoughts on their sailing and crewing skills. But it doesn't end there—they also give their brutally honest opinions on what it's truly like to sail and live aboard Nauti Dogs with me as their captain. Expect laughter, candid revelations, and genuine insight into the realities of life at sea. Don't miss this hilarious and heartfelt conversation! Join the Sailing Doodles Navy! https://sailingdoodles.podia.com

Join us in this episode as we dive deep into why Gone with the Wynns made the surprising decision to sell their beloved sailboat! We’ll unpack what this means for their sailing adventures and what's next for this adventurous couple. Plus, explore the exciting world of wind-powered cargo ships and how they could revolutionize maritime shipping, and get an adrenaline boost as we cover the latest from SailGP, sailing's fastest-growing international racing league! Join the Sailing Doodles Navy! https://sailingdoodles.podia.com

In this special Q&A episode, I answer the most burning questions from YOU—our amazing Sailing Doodles community! From my thoughts on single life and past relationships to the future of the channel, the catamaran situation, upcoming adventures, and the realities of life at sea, we cover it all. Join the Sailing Doodles Navy! https://sailingdoodles.podia.com