Sailing Doodles Podcast

Sailing Doodles
  • 4.5 (8)
  • Places & Travel

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!

  1. Aug 25

    He Climbed Everest, Sailed Around the World & Conquered the Northwest Passage

    In this episode, I sit down with Gabriel, whose list of adventures is almost hard to believe. Most recently, he completed the legendary Northwest Passage aboard a 48-foot steel-hull trawler, navigating some of the most remote and challenging waters on Earth. But that’s only one chapter of his story. He has also circumnavigated the globe on a 48-foot sailboat, climbed Mount Everest, completed the Seven Summits, and swam the English Channel. We spend nearly an hour and a half talking about what it actually takes to attempt adventures like these—the preparation, the danger, the moments when things go wrong, and some incredible stories from places very few people ever get to experience. We talk about sailing through the Arctic, climbing the highest mountains on every continent, crossing oceans, swimming the English Channel, and what keeps someone searching for the next big adventure after already accomplishing so much. This is a different style of episode for the podcast, and one I’ve been wanting to do more of: sitting down with interesting people who have lived extraordinary lives and letting them tell the stories themselves. Enjoy the conversation. here is the link to buy "Iron Will" https://www.yachtworld.com/yacht/2006-custom-sprague-9996693/

    He Climbed Everest, Sailed Around the World & Conquered the Northwest Passage

  2. Aug 19

    RV Life vs Boat Life — Which Is Actually Better?

    I’ve spent years living and traveling on boats, but lately I’ve been back on the road in the RV — and it got me thinking: which lifestyle is actually better? In this podcast, I compare RV life vs boat life from someone who has lived both. We talk about the cost, maintenance, freedom, comfort, travel, adventure, social life, living with dogs, and all the little things that make each lifestyle amazing — and frustrating. RV life is definitely easier in a lot of ways, but does boat life offer something you just can’t get on land? And the bigger question… could I ever give up boat life for RV life? Let me know in the comments: if you could choose only one, would you live on an RV or a boat?

    RV Life vs Boat Life — Which Is Actually Better?

  3. Aug 2

    There Are No New Frontiers Left

    For most of human history, people who felt trapped by their circumstances could leave everything behind and head toward a new frontier. They could escape their social class, family reputation, past failures, or limited opportunities and try to build something entirely new. But do those kinds of fresh starts still exist? In this episode, I explore why starting over may be harder today than it was for previous generations, why fewer people are willing to risk everything, and whether the world has simply run out of places where your past does not define your future. I also share a story from my own family history about an ancestor who, according to the story passed down through my family, was the thirteenth son of an English lord. With little chance of inheriting anything, he left England for the New World to build a life of his own. We discuss the influence of the frontier on American ambition and entrepreneurship, the uncomfortable truth that these lands were never actually empty, and whether technology, space, artificial intelligence, international living, and online businesses have become the new frontiers. Maybe there are no truly undiscovered places left. But perhaps the biggest frontier has always been the decision to walk away from the life you were given and attempt to create a different one. Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: 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/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles

    There Are No New Frontiers Left

  4. Jul 21

    What Kind of Boat Should I Buy Next?

    I’m back with the second half of my patron Q&A, and this time we’re talking about what kind of boat I should buy for my next adventure. Would a diesel Sea Ray-style express cruiser work for Florida, the Keys, the Bahamas, and potentially farther into the Caribbean? Or would I be better off with a trawler, a traditional motor yacht, or something designed for longer-range cruising? I discuss the features, size, speed, dinghy setup, and practical limitations I would consider before buying. I also answer questions about whether I would collaborate with high-performance powerboat channels, meeting up with other content creators while traveling, and how Cougar and Merlin react to the constant stream of new people joining the boat. Thanks to everyone who submitted questions. Let me know what boat you think would make the best next chapter for Sailing Doodles. Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: 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/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles

    What Kind of Boat Should I Buy Next?

  5. Jul 17

    I Was Wrong... Here's the Better Plan

    A few weeks ago I shared an idea that I thought could completely change the way people experience luxury sailing. Then I asked for your feedback. Hundreds of comments later—and one incredibly detailed blog from a viewer—I realized I had made some major mistakes. In this episode I explain what I got wrong, why the original model probably wouldn't work, and the new direction I'm considering. We dive into whole-boat memberships vs. cabin memberships, pricing, charter economics, premium weeks, refundable deposits, and how this idea might actually become a real business. I still don't know if this will ever happen, but it's already a much better idea because of your feedback. As always, I'd love to hear what you think. Would you join something like this? What would you change? Here is Sam's Blog post: https://sveoti.net/an-open-letter-to-bob-white-sailing-doodles-buying-a-yacht-for-you/ Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: 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/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles

    I Was Wrong... Here's the Better Plan

  6. Jul 15

    Why Does My Crew Keep Leaving?

    In this patron Q&A podcast, I answer some of the most common—and most interesting—questions viewers have been asking. I talk about what happened with recent crew members, how I find people to join the boat, the couple who were supposed to launch a Sailing Doodles spin-off channel, whether I’m in a relationship, my changing thoughts about Thailand, plans for the new catamaran, the Mediterranean, the flotilla, and whether I’m seriously considering buying a motor yacht and doing the Great Loop. I also tell a disturbing offshore story about a friend who hired a delivery captain to sail his yacht from the Mediterranean to the Caribbean. In the middle of the Atlantic, the captain suffered a serious mental-health crisis and threatened to jump overboard. My friend had to change course and divert the yacht to the Azores so the captain could safely get ashore and receive help. It raises an important question: what do you do when someone panics, becomes unstable, or simply cannot handle being at sea—with nowhere nearby to get off the boat? Thanks to all the patrons and viewers who submitted questions. Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: 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/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodles

    Why Does My Crew Keep Leaving?

  7. Jul 13

    I'm Buying YOU a Yacht?

    What if there was a better way to own a luxury yacht? I've been working on a business idea that I honestly can't decide is brilliant... or completely crazy. Imagine having access to a $1.4 million sailing catamaran that cruises the Mediterranean, Caribbean, Thailand and beyond, without having to buy the whole boat yourself. In this episode I walk through the concept, the numbers, the challenges, and the biggest objections I've already heard. Most importantly, I want YOUR feedback. Would you join something like this? What would make you say yes... and what would make you run away? Leave your thoughts in the comments. Your feedback may completely change this idea. Fill out the survey if you want to go in on this with me! https://docs.google.com/forms/d/e/1FAIpQLSf5cP4pI-etL7w761rhN6DqTA81sLEbRsI0KTpkF3Jhf31-kg/viewform?usp=dialog Download the Sailing Doodles Crew App on iOS and come join the Crew! https://apps.apple.com/us/app/sailing-doodles-crew/id6760212361 or join our Patreon http://www.patreon.com/sailingdoodles or become a channel member https://www.youtube.com/channel/UCkDwexrF43p_1QurfKFBCBA/join Donate Via Paypal to help http://www.paypal.me/sailingdoodles Our partners: 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/ #Sailing #YachtLife #Thailand #Malaysia #Catamaran #SailingDoodle

    I'm Buying YOU a Yacht?

  8. Jul 8

    Getting a Motor Yacht Instead?

    In this episode, I talk through a big realization about the future of Sailing Doodles: because of location, weather, and cruising seasons, I may only be able to film on my new catamaran about four months a year. That creates a real problem. If I want to keep making consistent boat content, I may need a second boat. So I’m thinking about buying a smaller motor yacht to keep in Florida and use for cruising the Bahamas, and maybe even doing parts of the Great Loop. I go through the different types of boats I’m considering, what makes sense for the channel, what fits the budget, diesel vs gas, speed vs efficiency, and whether a motor yacht could be the right move for the next chapter. Is this a smart backup plan, or am I just trying to talk myself into buying another boat?

    Getting a Motor Yacht Instead?
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Ratings & Reviews

4.5
out of 5
8 Ratings

About

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!

Information

  • Creator
    Sailing Doodles
  • Years Active
    2025 - 2026
  • Episodes
    147
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Sailing Doodles Podcast
  • Show Website
    Sailing Doodles Podcast

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