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
October 3, 2025 • 35 mins
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 inte...
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September 30, 2025 • 50 mins
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 finally selling everything to ch...
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September 25, 2025 • 36 mins
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 t...
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September 21, 2025 • 42 mins
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
...
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September 15, 2025 • 23 mins
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...
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September 12, 2025 • 31 mins
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 f...
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September 7, 2025 • 47 mins
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...
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August 17, 2025 • 37 mins
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 convers...
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August 7, 2025 • 30 mins
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 apprec...
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August 1, 2025 • 36 mins
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 ...
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July 25, 2025 • 21 mins
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 A...
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July 16, 2025 • 41 mins
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 succee...
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July 14, 2025 • 52 mins
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 ...
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July 1, 2025 • 25 mins
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 Ar...
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June 13, 2025 • 17 mins
What happens when Deadpool and Wolverine dive into the world of high-speed sailing?
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June 11, 2025 • 37 mins
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 ...
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June 5, 2025 • 29 mins
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...
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May 27, 2025 • 34 mins
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’s loving (and learning) about cruis...
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May 22, 2025 • 37 mins
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 headache...
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May 15, 2025 • 29 mins
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)
...
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