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!
Episodes
June 24, 2026 • 19 mins
Most people have a dream.
Maybe it’s sailing around the world, building a cabin in the mountains, starting a farm, opening a business, moving overseas, or just walking away from a life that looks successful on paper but doesn’t actually make you happy.
But most people never do it. Not because the dream is impossible, but because they keep waiting until they’re ready.
In this episode, I talk about why I be...
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June 22, 2026 • 32 mins
In this episode, I’m answering your questions from Patreon, YouTube members, and the Sailing Doodles app.
We start with the big one: my recent health scare, the blood clots and thrombosis, whether it could be connected to my past stroke, how medical care has been overseas, and what recovery might look like from here.
Then we get into the questions everyone always wants answered: What’s going on with Olivia? Is she...
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June 19, 2026 • 17 mins
After a big health scare, I’ve had to ask myself some hard questions about the future of Sailing Doodles.
I just bought my dream yacht, but now I’m dealing with blood clots and thrombosis in major abdominal veins, and I still don’t have all the answers about what caused it or what the long-term prognosis looks like. For a while, there was even concern it could be cancer, which thankfully seems to have been rule...
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June 16, 2026 • 19 mins
In this episode, I talk about the medical issue that suddenly interrupted my life and my plans for Sailing Doodles.
It started with abdominal pain that I thought might be something minor, but after hospital visits, scans, and more tests, doctors found inflammation around my pancreas and blood clots in the portal vein. For a short time, there was a real fear that it could be pancreatic cancer, which was obviously terrifying.
R...
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May 28, 2026 • 17 mins
After years of delays, setbacks, and finally taking delivery of my new Island Spirit 525e… I’ve run into another problem.
Because of Thailand’s import and customs rules, I now have to sail the boat roughly 72 hours to Malaysia, clear customs, and then sail all the way back to Thailand just so the yacht can legally return as a tourist vessel.
It’s expensive, time consuming, exhausting… and hones...
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May 24, 2026 • 32 mins
After years of planning, delays, factory visits, and a whole lot of frustration, my new Island Spirit 525e electric catamaran is finally in the water — and sailing.
In this episode, I talk through the last few crazy weeks of the build: inspecting the boat at the factory, the Buddhist blessing ceremony, the nerve-racking truck move to the marina, launching the yacht, and finally taking her out for the first sail and sea tri...
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May 7, 2026 • 40 mins
Electric boats are no longer some far-off future idea — they’re here, and my new Island Spirit 525e is a perfect example. With a 210 kWh battery bank, two 65 kW electric motors, and around 80 nautical miles of electric range at 6 knots, this is a serious electric propulsion system.
In this episode, I talk about the safety side of modern electric boats: lithium batteries, battery monitoring, cooling systems, electric ...
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May 7, 2026 • 34 mins
Dating while sailing around tropical islands sounds like it should be easy… but the reality is a lot more complicated.
When you live on a boat and cruise full-time, you are constantly moving from one place to the next. You are rarely in one place long enough to casually date, and most cruising destinations are full of couples, families, honeymooners, and retired cruisers — not single people looking to date.
Then ...
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April 13, 2026 • 15 mins
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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April 8, 2026 • 29 mins
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...
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March 21, 2026 • 47 mins
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 ...
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March 14, 2026 • 21 mins
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 incred...
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March 10, 2026 • 33 mins
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 t...
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February 21, 2026 • 29 mins
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-c...
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February 15, 2026 • 36 mins
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...
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February 12, 2026 • 34 mins
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...
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February 1, 2026 • 15 mins
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 be...
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January 26, 2026 • 23 mins
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 actual...
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January 19, 2026 • 24 mins
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 pr...
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January 10, 2026 • 12 mins
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 o...
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