- Sail Loot Podcast 048: Neil Davies Sails to Cuba and Works Remotely for Sailing Money
- Sail Loot Podcast 042: Wiley Sharp, Part 2 – Owning and Operating a Virgin Islands Sailing Charter
- Sail Loot Podcast 037: Salty Times Sailing to find the Surf with Base and Jamie
- Sail Loot Podcast 027: Couchsailors Jose and Gina Rent All of their Rooms for Sailing Money
- Sail Loot Podcast 020: Leah Kruger Makes Her Sailing Money With Brio
- Sail Loot Podcast 019: Good Anchorage, Get Paid To Cruise
- Sail Loot Podcast 013: Investing Money to Make Money While Sailing the Mediterranean with Franz Amussen
- Sail Loot Podcast 012: From Corporate America to Ottsworld with Sherry Ott
- Sail Loot Podcast 010: Zero To Cruising To Chartering One Love with Mike and Rebecca Sweeney
- Sail Loot Podcast 009: The Overnight Success Dream – It’s a Myth. Get Over It
Sail Loot Podcast 046: Captain Randy Smith With Sail Libra and Orange Beach Sailing Adventures
I want to be back on the water sailing Libra wherever she’s going. Captain Randy’s prediction was correct. As soon as we pulled into the dock at the Strictly Sail Miami Boat show, I wanted to get out on the water with Sail Libra.
Don’t get me wrong, I definitely wanted to go to the Miami Boat show, and I had an amazing time there, but the voyage there on S/V Libra was an AWESOME experience. I’ve still got a smile on my face thinking about the adventure.
It was always my plan to go to the Strictly Sail Miami Boat show. I had some sky miles so I was able to grab my flights for “free”, but then I talked to Captain Ryan in Episode 044 of the Sail Loot Podcast. That’s when I decided that maybe I should jump on the trip on S/V Libra and sail to the boat show instead! I am so glad that I made the decision to jump on board.
I have to give some props to Annie Dike at Have Wind Will Travel. After all, she’s the one that emailed me a few months ago and said that Captain Ryan Rayfield had an amazing story that I might want to share. Then the small world of sailing and cruising started opening up.
I went down to charter a sailboat with some friends in the BVI and had the opportunity to meet Scott and Brittany from Windtraveler and Aristocat Charters. The next thing you know I’m talking to Ryan Rayfield for a podcast while seeing updates on Facebook that Captain Randy is helping deliver Scott and Brittany’s new sailboat across the Atlantic. A little over a month later I’m meeting Captain Ryan, Captain Randy, Annie, Phillip, and the rest of the Pensacola to Miami Sail Libra crew – Andy, Billy, Sophia, and Jeff – for dinner and drinks at a bar in Pensacola the night before we take off on our trip across the Gulf of Mexico.
When the Sail Loot Podcast started I said that in the future, my plan is to take the podcast cruising with me. I try to envision the conversations that I have like we’re sitting in the cockpit of a sailboat chatting about how the heck we were lucky enough to be there, what our costs were, what our budget was, how we are able to afford it, and the opportunities that presented themselves along the way to find our sailing money and get us to the point where we were living a life rich in experiences.
I got to live one of those amazing experiences sailing across the Gulf of Mexico to the Strictly Sail Miami Boat show and sitting down in the cockpit of S/V Libra with Captain Randy chatting about how he was able to make a living doing something that he’s passionate about…sailing.
A Few Things You’ll Learn about Captain Randy Smith, Sail Libra, and Orange Beach Sailing Adventures in this episode:
- How Captain Randy went from growing up on a wheat farm in Wellington, Kansas to a sailing captain.
- Captain Randy’s first sailboat in San Diego and how much it cost.
- How much he sold his first sailboat for (it was more than he bought it for).
- How Captain Randy has been able to make sailing affordable.
- Learning to sail and learning about deals on sailboats during Wednesday night beer can races.
- Happy Valentine’s Day Kim!!!
- Making a deal with himself to never live somewhere where the average temperature was less than his age.
- Captain Randy’s plans to play music at tiki bars.
- Randy’s jobs before he became “Captain” Randy.
- Construction sales and elevating homes post-Katrina with Orleans Shoring.
- Putting corporate America on sabbatical on S/V Attitude with his brother and nephew.
- Moving S/V Attitude‘s homeport for Orange Beach, AL
- Purchasing S/V Attitude
- Moving S/V Attitude to Bear Point Harbor Marina
- Captain Randy wants a free bushwacker!
- Meeting Captain Bo Cordle and setting up some charters on S/V Lattitude and S/V Attitude with help from Captain Ryan
- Why Bo and Randy set their prices a little higher than Captan Ryan’s
- The mother of necessity. Bo was moving on to start his sailing adventure and Captain Ryan was too busy and overbooked at Orange Beach Sailing Adventures. This was the perfect opportunity for Captain Randy.
- Why Captain Randy loves taking people out sailing with Orange Beach Sailing Adventures and Sail Libra.
- Teaching people to be self-sufficient on a sailboat on S/V Libra.
- The fantastic people that you’ll meet on a passage on S/V Libra. I had never met the 8 other people on board. I’ve got 8 new friends!
- Captain Randy helps with deliveries of sailboats when Sail Libra isn’t on a passage.
- And much more!
Links and Resources from this episode:
- Sail Libra
- Orange Beach Sailing Adventures
- Sail Loot Podcast 044: Sail Libra with Captain Ryan
- Orleans Shoring – Go to the Our Staff page – here– Captain Randy is on the 2nd row of that picture!
- Bear Point Harbor Marina
- Sailing B & A
- Junior Captains
- Have Wind Will Travel
- Defender – Marine Outfitter
Thank you very much for listening to the show! If you enjoyed listening, it has helped you in any way, or you know somebody else that would enjoy it, please share it using the social media buttons that you see on the page.
Additionally, reviews for the Sail Loot podcast on iTunes are extremely helpful and greatly appreciated! They do matter in the rankings of the show and I read each and every one!
Lastly, if you have any questions or comments please leave them below or go ahead and send us an email via the Contact page!