If you live in Northeast Florida and sailing is on your bucket list, there’s no excuse not to get out on the water. First Coast Magazine recently teamed up with a couple of sailing schools in the area to see how the average landlover (me) could break into sailing. Our waterways are so diverse. The river and its serene, woodsy inlets is a different experience than the wide-open horizon of the ocean, while the Intracoastal Waterway has an array of wildlife. To get a taste of sailing in a variety of waters, we asked Windward Sailing in Fernandina Beach and Southern Sailing Academy in Jacksonville at Julington Creek to be our guides.

Windward Sailing



We start our adventure on a Saturday morning in Fernandina Beach. Windward Sailing School is housed in a charming historic home on the corner of 8th and Beech Streets, not far from the marina. We begin the lesson in the classroom where owner Tony Jones and founder Charlie Weaver provide an overview of important nautical terms. This is a key step in learning to sail. Not knowing the language can be dangerous for everyone. For instance, when someone yells, “Jibe!” you’d better duck. For those on deck, this means that the boom, a heavy pole running along the bottom of the sail, is about to swing across the boat.

“We call it a boom because that’s the sound it makes if you’re not careful and it hits you in the head,” jokes Charlie. He teaches us the terms by using a handcrafted wooden model that he built himself several years ago. “There’s no way around the nomenclature,” he says. “In sailing, a winch is a winch.”


Charlie sold the school to Tony in 2005, but he continues to work as an instructor. Back in the 1990s, Weaver and his wife decided to open the school after seeing a lot of bad sailing. “We sailed for three and a half years, and while we were out there, we saw so many people who didn’t know what they were doing,” he says. So they selected a prime sailing location and established the school. “It is such a wonderful sailing area: real close to the ocean, deep water right off the pier, and good wind almost all the time.”

In the classroom, Tony explains that Windward Sailing offers different levels of certification through the American Sailing Association (ASA), a large network of sailors and sailing schools. “It’s two and a half days of training for each level,” he says.

Once you earn your certificate, you can take it to almost any dock in the country and rent a sailboat. The class we are sampling is an ASA 101 class. In this course, the boat stays in the Amelia River, but the next level sails into the ocean. The third level is an overnight class, where students spend two nights onboard.


After the class, we head down to the dock. We have a team of instructors helping out: Charlie, Tony, John Drake, Jerry Miller and Bob Kidd. It’s clear and sunny, but not too hot, and we spot several dolphins in the water. “We see lots of wildlife,” says Tony. “Dolphins, manatees and wild horses up in Cumberland.”

On the boat, we try to apply our newly learned terminology and help out the crew, but we’re slightly overwhelmed by all of the activity. They shout rapid commands to one another in nautical speak, and there’s a lot of cranking and sail flapping and rope-winding. Nonetheless, we enjoy the ride, and I even get a chance to steer the rudder.

Southern Sailing Academy



On a warm evening later that week, we drive down to Julington Creek to check out Southern Sailing Academy.

No classroom or textbooks this time around. We hop on the boat and get started right away. Tonight we are tagging along with other sailing students: Kathy O’Shea and her husband, Nixon Binney. Also in training is Allin Popescue who is learning to be a sailing instructor.  Kathy and Nixon are learning to sail for the first time, but this is their third day out on the boat. When I ask Kathy why they wanted to start sailing, she says, “We vacationed down in the Abacos and envied people on their boats. We kept saying we want to do that some day.”


Kathy assures me that the overwhelming feeling I had on the first sailing lesson is perfectly normal. “It’s confusing more than hard. There’s a lot to remember at first,” she says.

Once again, the weather is fantastic, but the surroundings are very different from the much saltier environment of Fernandina Beach. The water here is lined with trees on all sides, and the “creek” is more like a huge lake with a current.

Southern Sailing Academy owner Don Shapray has been sailing for decades, and his company has taught more than 15,000 students. “I’m still teaching just about every day,” Don says. At one point he was operating sailing schools in other parts of the country including Marina Del Ray, California and Houston, Texas. Currently, Southern Sailing operates out of three locations in Florida: Jacksonville, Destin and Panama Beach.


As the evening grows darker, we sail back toward the pier and the students take down the sail. It can be very difficult to actually sail the boat right back up to the dock, says Don. So we use the little motor to get back to our spot. Kathy and Nixon seem like pros now, as we watch them fold and tie down the sail and place it in its protective cover. They have completed their third lesson out on the water, but there is one final step before they earn their sailing certificates. Every student is required to pass a written test, says Don. Once that’s done, Kathy and Nixon can rent a sailboat anywhere in the world with their certification. I imagine they will return to the Abacos very soon and cross one more thing off their bucket list!