Sailing Doodles Podcast

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 Phillip@inspiredyachting.com 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 Phillip@inspiredyachting.com 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 Phillip@inspiredyachting.com 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 Phillip@inspiredyachting.com 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

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 Phillip@inspiredyachting.com 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