Ryan Rayfield


Ryan hold20151218_064509s a 100 Ton Master USCG license and is on his 3rd renewal.  Ryan has been sailing since he was a child starting on the lakes of Alabama and then in Asia for the better part of his twenties, doing day charters and deliveries throughout Thailand and Malaysia.

Working in corporate America for Delta Airlines as a computer systems engineer and programmer served as the perfect opportunity for Ryan to see and sail the world.  He gave it all up in 2007 and moved to Orange Beach, Alabama to pursue a nautical career with his boat.  He ended up starting one of the most successful day sail operations on the northern Gulf of Mexico Coast with “Orange Beach Sailing Adventures,” taking visitors to the area on sunset cruises and specialized sailing trips.

For eight years now he has been growing and building the #1 “Trip Advisor” rated activity on the Alabama Gulf Coast.  He now will spend summers during hurricane season running Orange Beach Sailing Adventures and winters running SV Libra on adventure cruises focusing on the Cuban and Caribbean areas.  Ryan has two children, Sierra and Spencer.


Randy Smith


Older (but not necessarily wiser!), Randy brings a colorful sailing background of cruising and deliveries.  Growing up on a wheat farm in Kansas may not be the typical start for a sailboat captain, but Randy made his way to San Diego after college and instantly fell in love with the wind and water.  Each weekend he would change his suit and dress shoes for shorts and flip-flops, and trade stop-and-go traffic for tacking and jibing.  Most importantly, turning the dream of living on his sailboat into his new reality.

Thousands of miles later, with experience crossing the Atlantic and the Gulf of Mexico, as well as cruising the Caribbean and the Pacific, Capt. Randy is now at port in Orange Beach, Alabama and living his “bucket list” lifestyle.

Capt. Randy is a licensed USCG Master Captain, offering both charter captain and boat delivery services. He spends hurricane season captaining the second boat in the Orange Beach Sailing Adventures fleet but is most excited about sailing with you on SV Libra, and sharing your next adventure!