Episodes

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 save lives. We’ll talk about: How hurricane forecasting has changed in just a few decades The role of S...

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 “parasite smuggling” really is, and why this growing underwater drug tactic is spreading around the w...

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 shares his honest opinions about carrying weapons onboard and the risks every cruiser faces when cros...

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 next for Sailing Doodles in 2026. Drop your next questions in the comments for the next Q&A episode! E...

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 sailing channel when the journey’s done. In this episode, I explain what I’m looking for, what the experie...

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 buying and selling fairer, and what this means for the future of yacht sales. If you’ve ever thought ...

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 attention (and snacks), interrupted mid-sentence, and even forced an unexpected break for feeding time. It’s m...

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 everything behind to chase a life at sea The early struggles of creating a sailing show with a bigger purpose...

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 Planning & paperwork for international cruising Boat ownership, chartering, and insurance lessons Li...

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 inclu...

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 t...

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% myt...

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 ab...

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 ...

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...

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...

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! ...

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...

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...

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...

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...

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 wa...

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...