Sailing Doodles Podcast

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...

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 abo...

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...

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’...

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 bo...

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 (...

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...

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 Engi...

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...

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 Benete...

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-...

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, upgr...

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...

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...

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 fro...

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 Marina...

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 saili...

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...

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! h...

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/