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...
Sep 15, 2025•24 min•Season 1Ep. 99
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 storie...
Sep 12, 2025•32 min•Season 1Ep. 98
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 ...
Sep 07, 2025•47 min•Season 1Ep. 97
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...
Aug 17, 2025•38 min•Season 1Ep. 96
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, ref...
Aug 07, 2025•30 min•Season 1Ep. 95
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! ...
Aug 01, 2025•37 min•Season 1Ep. 94
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 fo...
Jul 25, 2025•22 min•Season 1Ep. 93
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 s...
Jul 16, 2025•41 min•Season 1Ep. 92
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? T...
Jul 14, 2025•52 min•Season 1Ep. 91
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.arunaligh...
Jul 01, 2025•26 min•Season 1Ep. 90
What happens when Deadpool and Wolverine dive into the world of high-speed sailing?
Jun 13, 2025•17 min•Season 1Ep. 89
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 wa...
Jun 11, 2025•37 min•Season 1Ep. 88
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...
Jun 05, 2025•29 min•Season 1Ep. 87
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, chang...
May 27, 2025•35 min•Season 1Ep. 86
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...
May 22, 2025•37 min•Season 1Ep. 85
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 saf...
May 15, 2025•30 min•Season 1Ep. 84
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 ...
May 09, 2025•42 min•Season 1Ep. 83
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 n...
May 05, 2025•36 min•Season 1Ep. 82
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 ne...
Apr 20, 2025•38 min•Season 1Ep. 81
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 H...
Apr 16, 2025•32 min•Season 1Ep. 80
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 war...
Apr 14, 2025•31 min•Season 1Ep. 79
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...
Apr 08, 2025•32 min•Season 1Ep. 78
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!
Apr 03, 2025•16 min•Season 1Ep. 77
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 t...
Mar 29, 2025•39 min•Season 1Ep. 76
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! http...
Mar 24, 2025•21 min•Season 1Ep. 75
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
Mar 21, 2025•42 min•Season 1Ep. 74
In this week's boating news update, tragedy strikes at the Imperial Yacht Club Marina as a devastating fire destroys multiple yachts, shocking the maritime community. We also dive deep into the uncertain future of the iconic SS United States—will this historic ocean liner finally meet its end, or is there hope yet? Plus, major shifts in the marina industry as Blackstone acquires Safe Harbor Marinas, potentially impacting thousands of boaters nationwide. Join us as we uncover the full stories beh...
Mar 19, 2025•18 min•Season 1Ep. 73
Ever wondered who actually lives on boats full-time? Are they all retired millionaires, or is it possible for anyone to start cruising? In this video, we break down the REAL stats on liveaboards and cruisers—how much experience they actually have, how they afford it, and the #1 mistake that ends most cruising dreams. We’ll cover:** ✅ The average age of new liveaboards & cruisers ✅ How much sailing experience they have (it’s less than you think!) ✅ Marina life vs. full-time cruising—who actua...
Mar 13, 2025•12 min•Season 1Ep. 72
Mar 10, 2025•23 min•Season 1Ep. 71
I'm starting a new topic for this podcast. Sailing News! In this episode I cover the recently completed Vendee Globe around the world solo sailing race, the advancement of autonomous and AI powered boats, catch the final ruling on the 3 abandoned vessels of the 2024 Newport Bermuda Race and give you updates of the popular sailing shows like Sailing La vagabonde, SV Delos and Sailing Doodles. Want to support this channel? Join the Sailing Doodles Navy https://sailingdoodles.podia.com...
Mar 04, 2025•18 min•Season 1Ep. 70
