The Bobby White Podcast is hosted by Bobby White, creator of Sailing Doodles and a former international airline and private jet pilot. He shares stories from his life as a pilot, sailor, traveler, and adventurer, covering aviation, sailing, travel, business, and living abroad. Episodes also feature conversations with interesting people he has met along the way. The show focuses on real experiences and memorable adventures, and was formerly known as The Sailing Doodles Podcast.
Episodes
Did I Save My Father's Life? The Lynyrd Skynyrd Tragedy
On October 20, 1977, Lynyrd Skynyrd's chartered Convair 240 crashed in Mississippi after running out of fuel, killing six people, including three band members and both pilots.
But what most people don't know is that my father, Jim White, was the chief pilot for Falcon Aviation and had been flying Lynyrd Skynyrd on their tour. Just days before the crash, he left to be home for my birth. I was born
I Flew Sammy Hagar on Tour… and Got the Nickname “Silvertoes”
Back in 2003 or 2004, I was just 24 years old and had landed my first real job flying private jets out of Van Nuys, California. One of my very first assignments? Flying rock legend Sammy Hagar and his band around the country on tour!
For the next month or two, I got a behind-the-scenes look at life on the road with a rock star. We had all-access backstage passes, hung out with the band, drank mar
We Thought They Were Pirates! The Real Dangers of Sailing Around the World
How dangerous is it really to sail around the world? Are pirates something sailors should actually worry about?
While sailing through Indonesia, we stopped at a tiny, remote atoll hundreds of miles from civilization. Just as we were preparing to leave, a wooden boat carrying six men headed straight toward us. With only me and two women aboard, we had no idea what they wanted. What happened next w
I Was a Flydubai Pilot… Here's What Went Wrong
I was one of the very first pilots hired by Flydubai back in 2009, and I was there for the airline's very first passenger flight. But after a little over a year flying the Boeing 737 for them, I decided to leave.
Following the recent shocking incident involving a Flydubai first officer, I'm sharing my firsthand experience working for the airline, the problems I saw with management and scheduling,
4 Years Flying Private Jets in Africa — Bribes, Guns and Gaddafi
Before YouTube, I spent four years living in Nigeria and flying a Gulfstream III all over Africa for a wealthy businessman.
In this episode, I tell some of my favorite stories from that time — living in Maiduguri and Abuja, dealing with police bribes, flying across Africa, mechanical problems in the middle of nowhere, bird strikes, armed guards, and some very unusual passengers and destinations.
Why I’m Selling My 56-Foot Sailboat
It probably looks like my 56-foot CT56 is falling apart, but there’s more to the story. After sitting on the hard unattended for over a year, I’m compressing a year’s worth of maintenance into just a few weeks.
In this episode, I break down what’s gone wrong, what I’ve fixed, what still needs to be done, and why I’ve decided it’s time to sell Nauti Dogs. I’m ready for something different — a smal
Aerosmith Never Knew Their Private Jet Had a Serious Problem
Before Sailing Doodles, I spent years flying Gulfstream private jets around the world, and for about six to eight months I was one of the primary copilots flying Aerosmith on tour.
Most nights we'd watch the show, leave halfway through to get the jet ready, then fly the band to their next city as soon as they came off stage.
But one night, flying Aerosmith home to Boston, I noticed something str
What's Really Happening with my Electric Catamaran?
In this episode I’m answering your questions about what’s happening with my electric catamaran, whether I’m keeping it, selling it, or moving back to diesel.
I Flew Snoop Dogg… Then Customs Brought the Drug Dogs
Back in 2004, I was a young Gulfstream III copilot flying celebrities around the world—and one of our regular passengers was Snoop Dogg.
On one particular trip, our company was bringing Snoop and his entourage home from Brazil. I joined the trip in Brownsville, Texas, where the airplane had to clear U.S. Customs and Immigration before continuing on to California.
Customs knew who was coming, and
Superyacht Ownership Explained by an Actual Owner
What is it actually like to own a superyacht?
I sit down with my friend Bob, who has owned yachts ranging from 65 feet all the way up to 165 feet, to get an inside look at the reality of superyacht ownership.
We talk about what these boats really cost to buy and operate, hiring and managing crew, maintenance, scheduling, fuel, marinas, itineraries, and all the logistics that come with owning a y
Burning Man Is Getting Older, More Expensive… and Losing Money
I’m recording this episode from the roof of my RV in the middle of Black Rock City at Burning Man 2026.
Burning Man has grown from a small gathering on a San Francisco beach into a temporary city of more than 70,000 people in the Nevada desert. But after decades of explosive growth, something is changing.
Tickets that once sold out almost instantly are now easier to get. The average Burner is ge
He Climbed Everest, Sailed Around the World & Conquered the Northwest Passage
In this episode, I sit down with Gabriel, whose list of adventures is almost hard to believe.
Most recently, he completed the legendary Northwest Passage aboard a 48-foot steel-hull trawler, navigating some of the most remote and challenging waters on Earth.
But that’s only one chapter of his story.
He has also circumnavigated the globe on a 48-foot sailboat, climbed Mount Everest, completed th
RV Life vs Boat Life — Which Is Actually Better?
I’ve spent years living and traveling on boats, but lately I’ve been back on the road in the RV — and it got me thinking: which lifestyle is actually better?
In this podcast, I compare RV life vs boat life from someone who has lived both. We talk about the cost, maintenance, freedom, comfort, travel, adventure, social life, living with dogs, and all the little things that make each lifestyle amaz
There Are No New Frontiers Left
For most of human history, people who felt trapped by their circumstances could leave everything behind and head toward a new frontier. They could escape their social class, family reputation, past failures, or limited opportunities and try to build something entirely new.
But do those kinds of fresh starts still exist?
In this episode, I explore why starting over may be harder today than it was
Will Nika Be Coming Back?
In this Ask Me Anything podcast, I answer some of the questions patrons and viewers have been asking most.
I start with Nika—whether she’ll be joining me again, how we got along, and what might be next. I also share the scariest experience I’ve ever had at sea: the night my old boat nearly caught fire and sank near Cape Hatteras. I included clips from the original video and explain what happened
My New Yacht Has Some Problems—Here’s the Full Story
Owning a brand-new hybrid-electric yacht has been exciting—but it has also come with a much steeper learning curve than expected.
In this podcast, I give an honest update on my first few weeks aboard the Island Spirit 525e. I walk through the technical issues we’ve experienced so far, including repeated generator faults, problems within the drive-battery system, charging limitations, and some of
What Kind of Boat Should I Buy Next?
I’m back with the second half of my patron Q&A, and this time we’re talking about what kind of boat I should buy for my next adventure.
Would a diesel Sea Ray-style express cruiser work for Florida, the Keys, the Bahamas, and potentially farther into the Caribbean? Or would I be better off with a trawler, a traditional motor yacht, or something designed for longer-range cruising? I discuss the fe
I Was Wrong... Here's the Better Plan
A few weeks ago I shared an idea that I thought could completely change the way people experience luxury sailing.
Then I asked for your feedback.
Hundreds of comments later—and one incredibly detailed blog from a viewer—I realized I had made some major mistakes.
In this episode I explain what I got wrong, why the original model probably wouldn't work, and the new direction I'm considering. We d
Why Does My Crew Keep Leaving?
In this patron Q&A podcast, I answer some of the most common—and most interesting—questions viewers have been asking.
I talk about what happened with recent crew members, how I find people to join the boat, the couple who were supposed to launch a Sailing Doodles spin-off channel, whether I’m in a relationship, my changing thoughts about Thailand, plans for the new catamaran, the Mediterranean, t
I'm Buying YOU a Yacht?
What if there was a better way to own a luxury yacht?
I've been working on a business idea that I honestly can't decide is brilliant... or completely crazy.
Imagine having access to a $1.4 million sailing catamaran that cruises the Mediterranean, Caribbean, Thailand and beyond, without having to buy the whole boat yourself.
In this episode I walk through the concept, the numbers, the challenges
Getting a Motor Yacht Instead?
In this episode, I talk through a big realization about the future of Sailing Doodles: because of location, weather, and cruising seasons, I may only be able to film on my new catamaran about four months a year.
That creates a real problem. If I want to keep making consistent boat content, I may need a second boat.
So I’m thinking about buying a smaller motor yacht to keep in Florida and use for
Stop Waiting Until You’re Ready
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 abo
The Questions I’ve Been Avoiding… Health, Olivia & What Happens Next
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
Is This the End of Sailing Doodles As I Know It?
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
My Health Scare: Cancer Fears, Blood Clots, and What Happens Next
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, whi
I Really Don’t Want To Do This
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 honest
The Truth About My New Electric Catamaran
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
Is Electric Sailing Finally Safe? Lithium, Lightning & My 210 kWh Catamaran
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, cooli
Dating in Paradise Is Harder Than You Think
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 looki
The Bahamas Raised Fees Too Far… Now They’re Reversing Course
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
Chloe Opens Up… And Drops Some Big News
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 som
Big Updates… New Boat, Chloe, & What’s Next
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
This Scares Me… AI Might Replace Creators Sooner Than We Think
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 im
How I Moved My Dogs From the U.S. to Thailand (The Real Process) | w/ AE Pets International
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 m
Why I Bought an Electric Catamaran (And What Could Go Wrong)
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 wo
The Pilot Behind Flying Doodles: Emma
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
Who’s REALLY Coming to Thailand With Me?
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
The New Boat Is Almost Done… I’m Flying to Thailand
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 journe
Why Most Sailing YouTube Channels Fail After 2 Years (And Why It’s Harder Now)
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 actua
Who’s Going to Thailand With Me? (New Boat, New Crew, Big Changes)
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 whi
RV Nightmare UPDATE: How Camping World Stepped Up & Made It Right
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 e
My Thoughts on the Greg Biffle Crash
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
Relationships, Insurance & the New Boat - Ask Me Anything
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
Everything You Think About Sailing Is Wrong
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
The Insurance Saga Is Finally Over… Here’s What I Can Say
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
Sailors Invented Half Our Language?!
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 sa
Stop Wasting Money on These Boat Fixes!
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…
Hot Babes, New Boat, and What’s Next for Sailing Doodles
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
• Li
Drove Off the Lot — and the RV Broke Down Immediately!
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 w
Avoiding Disaster: The Truth About Hurricane Season for Sailors
In this episode, I dive into how sailors and cruisers deal with one of the biggest threats on the ocean — hurricanes.
Fifty years ago, crossing an ocean meant hoping you didn’t run into a storm. There was no internet, no satellite tracking, and little warning. Today, we carry a weather computer in our pocket, with live hurricane data, Starlink connectivity, and routing tools that can literally sa
Dead Diver, Lost Cocaine, and the Australian Superyacht Scandal
A Queensland superyacht agent was offered $300,000 for a “simple” job — help two divers enter Australia. Days later, one diver was dead, another had vanished, and 100 kilos of cocaine were floating in Newcastle Harbor.
In this episode, Captain Bobby White of The Sailing Doodles Podcast breaks down the true story of James Blake Blee — how financial desperation led to a deadly smuggling plot, what
Yacht RAID in the Bahamas! Guns, Cash & Chaos
A U.S.-flagged motor yacht was raided by Bahamian authorities in Bimini after a tip-off — and what they found shocked everyone. Ten people were arrested, including the crew, and officers seized a cache of weapons, ammunition, and cash.
In this episode, Captain Bobby White of Sailing Doodles breaks down the facts, shows footage from the local news, takes a look at the yacht’s charter listing, and
Are Laura and I Getting Back Together? | Sailing Doodles Podcast Q&A
This week’s Sailing Doodles Podcast gets personal. Viewers submitted hundreds of questions — and of course, the most common one was about Laura.
Are Laura and I getting back together? What really happened behind the scenes at the Annapolis Boat Show? And how does Miss Lone Star fit into all this?
I also answer your questions about the new catamaran, future flotillas, the boat raffle, and what’s
From Viewer to Crew — I’m Looking for the Next Sailing Doodles
This might be the biggest announcement I’ve ever made. I’m looking for two people — ideally a couple — to come sail with me in Thailand this February for four months.
You don’t need sailing or editing experience. I’ll teach you how to sail, how to film, and how to create a YouTube channel like Sailing Doodles.
The goal? To train the next generation of creators and help them launch their own sail
Are Boat Brokers Ripping You Off? How Current Yachts Is Changing the Game
At the Annapolis Boat Show, Bobby sits down with Amanda and Maryline from Current Yachts, a new brokerage that’s shaking up the traditional 10% commission model. Instead of sky-high broker fees, they’re offering a flat-fee, transparent system — just $1,500 to list your boat and à-la-carte options for everything else. We dive into why they believe the old system is broken, how they’re making boat b
Laura Returns! The Wildest Podcast Yet (with Babies & Boat Shows)
Fan-favorite Laura from Sailing Doodles Seasons 2 & 3 is back! She joined me at the Annapolis Boat Show with her two young kids, and things got a little… chaotic.
We catch up on what Laura’s been up to since her sailing days, talk about motherhood, life after the show, and the possibility of getting back on the water.
This one’s totally “wheels off” — her 14-month-old demanded plenty of attentio
The Wild Story Behind Expedition Drenched – How Nate Turned His Dream Into a Global Mission
What started as one man’s dream to sail the world has grown into one of the most ambitious and inspiring sailing projects on YouTube. In this episode of The Sailing Doodles Podcast, I sit down with Nate and Amy from Expedition Drenched to uncover how it all began — from filming underwater expeditions to building a worldwide nonprofit that protects the oceans.
We talk about:
How Nate left everyth
Is the Caribbean Becoming Too Dangerous for Cruisers?
Sailing the Caribbean has always been a dream — but is it getting riskier? Between rising fees in the Bahamas, U.S. drug-interdiction ops near Venezuela, and shifting maritime laws, we dive into whether the Caribbean is still the paradise sailors imagine.
In this Q&A episode, I answer fan questions on:
Safety in the Caribbean today
Rising costs in the Bahamas & alternatives like Cuba and the BVIs
From Living in Nigeria to Living on a Yacht, My Story
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
Retire & Sail Away? Here’s the Truth
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 t
Giving Away My Boat?! What's the future of Sailing Doodles?
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, a
5 Strange Maritime Laws That Still Apply Today
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
Mistakes, New Catamaran Update & Spicy Crew Questions
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
Lost Lauryn on Motorbikes, Sailing & Adventure Travel
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
Sailing Miss Lone Star: Life, Sailing, and Baby on Board
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
Addressing the Drama: A Heartfelt Response and Sydney’s Appreciation
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
The Scariest Dangers at Sea (And How to Survive Them)
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
FIRST LOOK: My New Catamaran is Almost Here!
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
The Truth About Running a YouTube Channel (It's NOT Easy)
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 fu
Who’s My Favorite Crew Member of All Time?
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 wer
Did The Bahamas Just Screw Themselves with These New Cruising Fees?
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 cru
Deadpool & Wolverine Buy a SailGP Team?!
What happens when Deadpool and Wolverine dive into the world of high-speed sailing?
Wrecked Boat Update!
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 t
The Real Cost of Living on a Sailboat – What Cruising Actually Costs!
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 do
From the Runway to the Sailboat – Meet Our New Crew Member Jennifer Brown
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’
The Truth About My Crew, My Boat, and What’s Next...
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 an
Where Should You Sail? The Ultimate Guide to Global Cruising Grounds
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
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
Cruising Isn’t All Sunshine: The Real Work of Boat Maintenance
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 troubleshootin
Insurance, Solar, and Catamarans: The Real Cost of Boat Ownership
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 o
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