Episodes

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 tom...

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...

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 pack...

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...

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...

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...

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...

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 The...

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!

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...

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...

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

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...

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 actually ...

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

I answer all your questions about sailing with dogs and so much more. Several times a month I takes questions from our patrons and channel members and give it my best shot to answer them all! https://www.patreon.com/sailingdoodles

Should you retire in Thailand! absolutely yes and I will tell you why in this podcast. An Ask Me Anything edition where I answer all my patrons and channel members questions. become a patron https://www.patreon.com/sailingdoodles

I sat down with Captain Glenn Shephard of the Bravo show "Below Deck: Sailing Yacht" at the Annapolis boat show and had a great discussion about his experiences on the hit show! Follow's Captain Glenn's social media to keep up with his adventures Instagram: https://www.instagram.com/capt_glennshephard/ Facebook: https://www.facebook.com/captainglennshephard Support the show by becoming a patron! https://www.patreon.com/sailingdoodles

I answer all the question from my Patrons and CHannel members about my new yacht, the Island Spirit 525e. Its a Sailing electric hybrid catamaran that I am going to sail around the world. For more info https://www.sailingdoodles.com/island-spirit-525e/

With Burning Man 2024 just wrapping up, I wanted to know how much does the average person spend to go there and what does the Burning Man Organization earn from the festival? Also, how much is spent in total by all festival goers to attend the festival? I answer all these question and more in the podcast.

We spent a week sailing around the Gulf of Naples and the Amalfi Coast in Italy and I give you my opinion on what it is like. From the costs, to the sights, I give you the run down on Italy

Rick Doblin is the founder of MAPS (multidisciplinary association for psychodelic studies), which just complete phase 3 trials for using MDMA to treat PTSD. They have an astounding success rate curing PTSD with 67% and addition 21% seeing good progress towards healing... thats 88% success in helping people live better lives. https://www.maps.org

I answer all of our patron's questions including: Should I get my medical back and fly part time again? Would you like to have your question answered on one of our Ask Me Anaything segments? Become a patron! https://www.patreon.com/sailingdoodles Link to the pay per view video: https://www.sailingdoodles.com/bvi-movie-final/ Link to my new catamaran Island Spirit 525: https://navigare-yachting.com/en/yacht-ownership/new-yachts/island-spirit/island-spirit-525-nn/209?ny=4163 Link the the Croatia F...