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PODCAST

Sailing Doodles Podcast

Bobby and Laura are sailing around the world with two full size labradoodles and document their adventures as they go! In the podcast series they will get more in depth on topics related to cruising in general and cruising with pets. Some of the information will be regionally specific and some will be a broader base. Come follow along with us and enjoy the ride!

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All Episodes

15:17

The Bahamas Raised Fees Too Far… Now They’re...

Sailing Doodles Podcast ·

2026/04/13

The Bahamas pushed cruising fees too far in 2025, and the boating industry says the fallout was immediate: fewer boats, weaker marina occupancy, and millions in lost economic activity across the islands. As of April 1, 2026, they’ve changed the system again. I’m breaking down the new official fee structure, comparing it to the old one, and showing what it means for a typical cruising boat heading to the Bahamas today.

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29:50

Chloe Opens Up… And Drops Some Big News

Sailing Doodles Podcast ·

2026/04/08

In this episode of the Sailing Doodles Podcast, I finally sit down with Chloe for a real conversation about her background, where she came from, and how she ended up joining the crew. It’s a fun, honest episode where you really get to know her beyond what you see in the videos… But we also share some important news. Chloe will be leaving Sailing Doodles for now to head home and take care of some medical things. We talk about what’s going on, what this means moving forward, and what’s next. It’s

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47:55

Big Updates… New Boat, Chloe, & What’s Next

Sailing Doodles Podcast ·

2026/03/21

In this episode of the Sailing Doodles Podcast, I’m answering your questions—from the new 525e catamaran build to future sailing plans, life in Thailand, and yes… Chloe. We cover everything from boat systems and upgrades, to where I’m sailing next, to how all of this actually works behind the scenes. Nothing is off limits in this one. Topics include: Status of the new Island Spirit 525e Future sailing plans (Maldives, Australia, beyond) Life and relationships on the road and at sea Boat systems,

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21:33

This Scares Me… AI Might Replace Creators Sooner Than...

Sailing Doodles Podcast ·

2026/03/14

For years I assumed I had another 5–10 years as a content creator before technology really started disrupting things. After seeing how fast AI video is advancing… I’m not so sure anymore. AI can now generate voices, scripts, music, and even realistic video scenes. I recently watched several AI-generated reels and videos that honestly fooled me at first. And the scary part is this technology is improving incredibly fast. In this episode I talk about: • AI-generated videos that fooled me • How fast

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33:03

How I Moved My Dogs From the U.S. to Thailand (The...

Sailing Doodles Podcast ·

2026/03/11

Ever wondered how hard it is to move pets internationally? visit AE Pets https://www.aepetsgo.com In this episode of The Sailing Doodles Podcast, I break down exactly what it took to move my two dogs from the United States all the way to Thailand. There are a lot more steps involved than most people realize — health certificates, government approvals, airline regulations, quarantine rules, and more. To help explain the process, I sit down with James from AE Pets International, the company that

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29:55

Why I Bought an Electric Catamaran (And What Could Go...

Sailing Doodles Podcast ·

2026/02/21

In this episode of The Sailing Doodles Podcast, I dive into one of the biggest decisions I’ve ever made… going all-electric with the new catamaran. Why did I choose an electric propulsion system? How does it compare to boats like Fountaine Pajot’s electric cats? What are the real risks — lightning, reliability, long-term maintenance? And what spares and tools will I be carrying to prepare for worst-case scenarios? Then we pivot into your most asked personal questions… – Will there be rotating

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36:13

The Pilot Behind Flying Doodles: Emma

Sailing Doodles Podcast ·

2026/02/15

In this episode of The Sailing Doodles Podcast, I sit down with Emma — the host of Flying Doodles — to talk about her aviation journey, career path, and what really goes on behind the scenes of the channel. From her flight training and early experiences in the cockpit to where she sees her aviation career heading next, Emma shares stories you haven’t heard before. We also talk about the future of Flying Doodles, upcoming projects, and what excites her most about aviation right now. If you’ve been

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34:00

Who’s REALLY Coming to Thailand With Me?

Sailing Doodles Podcast ·

2026/02/12

In this Ask Me Anything episode, I answer the question everyone keeps asking… Who is actually coming with me to Thailand to pick up the new boat? There’s been a lot of speculation about crew, plans, and what’s happening next — so I finally address it. I also talk about: Whether Chloe is joining me Lauryn? Thailand flotilla details What I actually have planned once I get there The current status of the boat raffle RV updates and the Camping World situation Craziest sailing mistakes I’ve ever seen

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15:47

The New Boat Is Almost Done… I’m Flying to Thailand

Sailing Doodles Podcast ·

2026/02/01

This one feels surreal to say out loud — the new boat is getting very close to completion. In this update, I share where the build is at, what’s left to finish, and why this moment feels different than anything before. After months (and years) of planning, I’ll be flying to Thailand next month to finally step onboard and start the next chapter. I know a lot of you have been following this journey from the beginning, and I can honestly say… I’m just as excited (and nervous) as you are. Thanks for

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23:30

Why Most Sailing YouTube Channels Fail After 2 Years...

Sailing Doodles Podcast ·

2026/01/26

Sailing YouTube looks easier than ever — bigger audiences, better cameras, more success stories. But the reality? It’s harder now than when I started, and most sailing channels don’t even make it past year two. In this episode, I break down why channels really fail — not because they can’t sail, but because they run out of money, burn out, struggle with people, or misunderstand how YouTube actually works today. I talk honestly about how long it took me to break even, living on beans and rice,

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24:21

Who’s Going to Thailand With Me? (New Boat, New Crew,...

Sailing Doodles Podcast ·

2026/01/19

In this podcast, I answer one of the biggest questions I’ve been getting lately: who’s coming with me to Thailand on the new boat? We talk about the new boat timeline, potential crew lineup, and what this next chapter of Sailing Doodles is really going to look—both on and off camera. I also address questions about Chloe, future appearances, and how I handle bringing new people into the videos while balancing privacy, reality, and the internet’s opinions. We also dive into: Who may be joining the

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12:53

RV Nightmare UPDATE: How Camping World Stepped Up &...

Sailing Doodles Podcast ·

2026/01/11

A month or so ago, I shared a podcast about the nightmare I was dealing with on my RV — and at the time, I hadn’t even gotten to the worst part yet: needing a full engine overhaul. In this episode, I give a full update on everything that happened afterward, how the situation evolved, and how Camping World ultimately stepped up and made things right. It was a long, stressful process, but in the end they took care of the problem, made me whole, and even got me into a newer and better RV. I believe

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18:43

My Thoughts on the Greg Biffle Crash

Sailing Doodles Podcast ·

2025/12/24

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

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39:07

Relationships, Insurance & the New Boat - Ask Me...

Sailing Doodles Podcast ·

2025/12/23

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

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23:15

Everything You Think About Sailing Is Wrong

Sailing Doodles Podcast ·

2025/12/07

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

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34:31

The Insurance Saga Is Finally Over… Here’s What I Can...

Sailing Doodles Podcast ·

2025/12/01

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

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35:20

Sailors Invented Half Our Language?!

Sailing Doodles Podcast ·

2025/11/28

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,

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15:09

Stop Wasting Money on These Boat Fixes!

Sailing Doodles Podcast ·

2025/11/13

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

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25:46

Hot Babes, New Boat, and What’s Next for Sailing Doodles

Sailing Doodles Podcast ·

2025/11/06

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

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8:05

Drove Off the Lot — and the RV Broke Down Immediately!

Sailing Doodles Podcast ·

2025/11/04

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

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110 results

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