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

Life aboard with crew, pets, and future sailing plans

Drop your thoughts in the comments — would YOU still sail the Caribbean right now?

Enter the contest here: https://raffall.com/398138/enter-raffle-to-win-sailing-doodles-sailboat-hosted-by-sailing-doodles

Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/

get tickets for the Annapolis Show:

https://annapolisboatshows.ticketspice.com/annapolis-sailboat-show?t=SailingDoodles

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 chase the dream of sailing full time. I’ll take you through the twists, setbacks, and adventures that brought me here today.

If you’ve ever wondered how Sailing Doodles started — this is the story behind it all.

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 include:

Why your health matters more than your bank account

How much money you really need to cruise full-time

Passive vs. non-passive income while sailing

Why your boat should be paid off before you cast off

The mental and lifestyle adjustments that make or break retirement cruising

Subscribe for more stories, tips, and real talk about life on the water!

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 topics like crew relationships, family, and even those AI “net worth” videos

Thanks to everyone who submitted questions on YouTube, Patreon, and Podia — you make these episodes possible!

If you want to submit your own questions for future podcasts, join our community here: [link to Patreon/Podia]

get tickets for the Annapolis Show:

https://annapolisboatshows.ticketspice.com/annapolis-sailboat-show?t=SailingDoodles

Make an appointment to see the Island Spirit 525e. Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/

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% myth

Courtesy flag fines & quirky traditions

Anchoring bans, seagrass zones, and “pay-to-anchor” politics

Crew contracts, Bible laws, and desertion rights

Have you ever been boarded, fined, or tangled up in a weird maritime rule? Share your story in the comments — I’d love to hear it.

get tickets for the Annapolis Show:

https://annapolisboatshows.ticketspice.com/annapolis-sailboat-show?t=SailingDoodles

Make an appointment to see the Island Spirit 525e. Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/

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 about the dogs, Burning Man, and life on the water

Huge thanks to our supporters who submitted these questions — if you’d like to be part of the next Q&A, join us on Patreon

 or as a YouTube Member.

Don’t forget to subscribe for more sailing adventures, podcasts, and behind-the-scenes updates!

get tickets for the Annapolis Show:

https://annapolisboatshows.ticketspice.com/annapolis-sailboat-show?t=SailingDoodles

Make an appointment to see the Island Spirit 525e. Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/

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 the water

What’s next for her in both motorcycles and sailing

It’s a fun conversation about chasing freedom, creating content, and living life off the beaten path.

Don’t forget to subscribe for more sailing stories, travel adventures, and conversations with fascinating guests.

This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy

https://sailingdoodles.podia.com/sailing-doodles-course-community

or become a channel member

https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join

or join our Patreon

http://www.patreon.com/sailingdoodles

Donate Via Paypal to help

http://www.paypal.me/sailingdoodles

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 come with chasing this lifestyle.

Make sure to check out Auburey’s channel Sailing Miss Lone Star and subscribe for more podcasts with sailors, cruisers, and adventurers from around the world.

Want to charter a boat in Greece! Check out Istion and get 10% off with out discount code "DOODLES10" Head over to: https://bit.ly/DOODLES10

This channel is funded by viewers like you. Please help us keep this channel creating great content by Joining the Sailing Doodles Navy

https://sailingdoodles.podia.com/sailing-doodles-course-community

or become a channel member

https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join

or join our Patreon

http://www.patreon.com/sailingdoodles

Donate Via Paypal to help

http://www.paypal.me/sailingdoodles

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, reflection, and a little behind-the-scenes honesty.

Let Sydney whip you into shape!

https://future.co/?code=sydney_p&rdrorigin=%2Fsydney_p

Want more info in the Island Spirit 525e? Be sure to say you saw it on Sailing Doodles. https://inspiredyachting.com/sailing-doodles-and-inspired-yachting-island-spirit-525e-referral/

Precision Sails:

https://www.precisionsailloft.com/request-for-quote/?utm_medium=affiliates&utm_source=sailing-doodles

Highfield Boats:

https://www.highfieldboats.com/

Here is the link for 5% off Total Boat:

https://www.totalboat.com/?sca_ref=7873710.M07fS3H4Xu

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!

Watch the full video of my scary moment catching fire around Cape hatteras.

https://www.sailingdoodles.com/fire-at-sea/

Check out Electrical Marine in Thailand

https://www.electrical-marine.com

Protect your boat with SerTec:

https://www.sertecmarine.com/en/