About Ryan Rayfield
Captain. Father. Teacher. Lifelong mariner.
Most offshore sailing programs don’t begin with a beached Sunfish and a battery-powered skiff. But Sail Libra isn’t run like most programs.
Ryan’s journey started at age 8 on Lake Martin, a sprawling body of water in central Alabama with nearly 900 miles of shoreline. His father gave him the freedom to operate a small 14-foot skiff powered by a heavy, battery-operated trolling motor—well before lithium batteries were common. Every evening, Ryan would carry the battery back to the garage to recharge it, and every summer his parents expanded the perimeter he was allowed to explore.
Eventually, he upgraded to a 15-horsepower Evinrude outboard, and that little skiff became his ticket to independence. One day, he spotted a derelict Sunfish washed ashore. With no owner in sight and no registration numbers, he towed it home behind the skiff. It had no sail or rigging, just a bare hull. So he did what any determined 10-year-old might do: pulled out the “S” volume of an encyclopedia, found a diagram of a sailboat, and used it to piece together his first rig.
It wasn’t pretty, but it worked. And he was hooked.
A Family-Run Operation
Today, Ryan operates Sail Libra, an offshore sailing school aboard a legendary 60-foot Bill Tripp Jr. ketch. It’s still very much a small family business. His children, Sierra (17) and Spencer (15), spend time aboard each year during holidays and summer breaks. In recent seasons, they've explored Long Island Sound and New York City, taking the train into Manhattan while Libra quietly anchors nearby.
Ryan with his Daughter Sierra in New England
One of their favorite traditions is Mate’s Week, when other crew families bring kids aboard for sailing, swimming, fishing, and campfires ashore. While Ryan keeps his kids’ time onboard separate from client passages, they remain a big part of the soul of Libra — and a reminder that Sail Libra isn’t a franchise or a content farm. It’s a home-grown program, built from the keel up.
When you book a passage aboard Libra, you’re not just signing up for adventure. You’re supporting a family-run business led by someone who’s spent his whole life drawn to the sea.
From Tech to Tides
Before turning full-time mariner, Ryan’s first career was in information technology. He began at Xerox, moved into the hospital sector, and then spent a decade with Delta Airlines, rising from systems administrator to senior .NET developer. That role sent him around the world solving high-stakes problems — from infrastructure failures to early cyberattacks — in the infancy of the connected world.
Along the way, Ryan chased bluewater miles in Southeast Asia, crew-hopping through southern Thailand and sharpening his offshore seamanship one unfamiliar deck at a time.
In 2003, while still at Delta, Ryan launched a tech company connecting consumers to arborist professionals. That venture flourished and allowed him to relocate to the Alabama coast. In 2006, he left Delta entirely to run the business full time and soon bought his first larger sailboat: a 37-foot Irwin ketch. Though not bluewater-rated, she was perfect for the shallow bays and low-clearance bridges of the Gulf Coast.
That boat sparked SailOB, a seasonal day charter operation that thrived during spring and summer tourist seasons. In the winter, Ryan took delivery jobs across the U.S. and Caribbean, quietly racking up real offshore miles in a variety of vessels and conditions.
Ryan putting a fresh coat of paint on Libra, assistance was was provided with a group of volunteers
Enter Libra
In 2013, Ryan purchased s/v Libra, a storied 60-foot Bill Tripp Jr. ketch that hadn’t sailed offshore in over 20 years. Over the next two years, he led a full-scale refit, modernizing the vessel while honoring her ocean-racing pedigree. During this phase, he continued operating SailOB while using Libra for advanced training trips throughout the Gulf of Mexico and Western Caribbean, including repeated runs to Havana and the Florida Keys.
Libra's first official offshore outing under Ryan's command was the 650-nautical-mile race from Pensacola to Havana, hosted by the Pensacola and Havana Yacht Clubs. She took first in class, marking a triumphant return to the open ocean.
In 2019, Ryan sold SailOB to the marina and shifted full focus to offshore training. Since that Havana race, Libra has logged more than 100,000 nautical miles, all under Ryan’s command.
The Captain’s Code: SCS Over SOS
Ryan’s leadership style is built on calm confidence and clear priorities:
Safety → Comfort → Sailing (always in that order)
Or as he likes to say, SCS over SOS. It’s a mindset that protects the boat and empowers the people aboard, one that Ryan lives by and passes on with every passage.
He takes pride in the details of Libra: systems that work under pressure, living spaces that feel inviting, and an environment that’s focused but never frantic. Racers often come aboard expecting to grind winches and be barked at, but Ryan teaches offshore sailing without the yelling and with a smile. There’s no ego here, only seamanship, the ocean treats everyone the same.
His goal is to send every client home more confident, capable, and comfortable than they were when they stepped aboard.
The younger years with Spencer
Advanced Firefighting Class, New Orleans, melting in the August southern heat, note the expression
Credentials That Go the Distance
While some operators choose less restrictive foreign registries (known as flags of convenience), Libra proudly flies the American flag — and Ryan meets the high bar that comes with it.
He holds a USCG 100-ton Master’s License with an Oceans Endorsement and the internationally recognized STCW II/3 credential, legally authorizing him to operate a commercial vessel under 500 GT on international voyages commercially anywhere in the world, specifically aboard U.S.-flagged vessels.
He completes regular continuing education and maintains all required credentials. His professional training includes:
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STCW Basic Safety Training
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Advanced Firefighting
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Medical Care Provider
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Bridge Resource Management
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Radar & ARPA
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ECDIS (Electronic Chart Display & Information Systems)
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Survival Craft and Rescue Boats
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Celestial Navigation
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OICNW (Officer in Charge of a Navigational Watch)
He also served as a Hollywood marine coordinator aboard Libra during the production of the feature film Mary, starring Gary Oldman — a unique role that blended real-world sailing and professional production logistics.
A Legacy Anchored in Encouragement
After sailing Libra for over 100,000 miles in the last 10 years, she has no plans of slowing down.
If you're looking for a true adventure, consider supporting a small, family-owned American operation — one that’s built not on clicks or content, but on experience, integrity, and a deep respect for the sea.
While Ryan’s style is entirely his own, he credits authors like John Kretschmer for shaping his philosophy on the sea. Kretschmer’s honest reflections on risk, confidence, and learning-by-doing helped reaffirm Ryan’s belief that experience, not ego, is what makes a sailor. That same mindset is now central to every Sail Libra passage.
Before his father passed away in 2012 from brain cancer, the two often spoke about Ryan’s dream to run an offshore sailing school. His father had studied Libra's design and told him, “If you ever get the chance — buy her. She’s a good boat.”
That chance came in 2013. Ryan took it, the story is still being written, read more about it here
Ryan and John Kretchmer before departing on a 1500nm tandem sail
“If it’s gonna happen, it’s gonna happen out there.” – Captain Ron (good movie for laughs!)
And when it does, Ryan will be at the helm, ready to guide, teach, and keep you safe while you find your sea legs.