Sail Loot Podcast 046: Captain Randy Smith With Sail Libra and Orange Beach Sailing Adventures

By on February 24, 2017

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.

S/V Libra the night that I met her.

The Libra Crew to Miami – From Left: Teddy, Annie, Phillip, Jeff, Captain Ryan, Sophia, Andy, Billy, Captain Randy

Captain Randy doing some teaching.

Captain Ryan showing Andy Jabba

Is Captain Ryan fixing something again?

A Sunset over the Gulf from S/V Libra

Andy, Teddy, and Sophia taking a Noonsite.

Teddy at the bow of S/V Libra, Annie and Phillip catching some rays, Andy in deep conversation and Captain Ryan…polishing some stainless.

It was sunset and calm so Annie decided to get up in the silks, Captain Ryan decided to capture it on the drone, and then Andy heard the rod bend at the stern of S/V Libra.

Some of the freshest Tuna I’ve ever eaten.

Jeff in some Libra gear

They called me Flava Teddy

I’m really just strapping a sail to the bow so it won’t fall overboard. Awesome pic though!

The final sunset on our Gulf crossing on S/V Libra to Miami

Sunrise over the Atlantic on our final morning on S/V Libra

The sunrise reflecting off of the Miami skyline

We made it! It’s time to Par-tay! Note: not to worry, she didn’t have any…but the rest of us did! Oh, and we don’t drink on passage.

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:


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About Teddy

I am a 37 year old that just wants to find a way to make a remote income, gather some Sail Loot and cruise the world! I have been sailing for a couple of years now, but mostly on 10 day trips as vacationing crew. I just recently took sailing to the next level by completing my Basic Keelboat, Basic Cruising, and Bareboat Cruising Certifications! I am also Vice President of a Medical Consulting Company, have a Mechanical Engineering degree from Georgia Tech, and have taken several Coding, Computing, and Online Business courses. It's time to share what I have learned!

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