Coy Theobalt's Sailing Story

Updated: May 23

" He wants to always “turn loose the reins” to give students ownership of the sailboat so that they can learn, knowing that he’s right there to support them and empower them. He believes in learning by doing."

Sailors can be a quirky and friendly bunch, and Captain Coy (real name: Coy Theobalt) fits this description to a tee. With a southern accent, Christmas lights strung in his cabin in February, and one of the kindest persona’s I’ve come across in a long time, he shared his love of sailing with me via a Zoom call while his amazing girlfriend, Charlie, cooked in the background, and Luigi the goat bleated outside their home. He’d just awoken from a nap when we connected for his interview, and I imagined that he would have looked similar if he had awoken to a storm at sea – calm, collected, attentive, and patient.

Captain Coy has traveled to many places and has many hours of sailing under his belt. When asked about his background, he shared that he once worked as a facilitator and leader for an organization that promoted experiential education for adults. He used to teach ropes courses and other activities in California and was always looking for new activities to teach to students. In 1998, he was in San Diego and that’s when he really started to get into sailing. Sailing became a passion and ever since, he kept working on bigger and bigger sailboats.


Captain Coy is originally from Hot Springs, Arkansas, and is a published author of the book, Gypsy Wind Speaks, Life Lessons from a Sailboat, a book about sailing adventures. He’s been a “water person” since he was 8 years old, when he decided he wanted to be a sailboat Captain. It took him a bit of time, but finally, at 50 years old, he did fulfill his childhood dream of becoming a Captain. His first boat was named Island Girl, and his second was the Gypsy Wind, a 57’ foot sailboat. She helped him fall in love with big sailboats. The Gypsy Wind was an old pirate ship and “a ton of fun,” he said, and also a “lot of hard work.” He offered trips for both full and half days and sunset tours, and he captained the Gypsy Wind till it was time to sell her. In 2012, he sold his boat, and in 2013, both him and Charlie retired and bought into a different sailboat with a few other couples.


Captain Coy teaches at Go Sail Flathead Lake in the Montana summers. Him and Charlie travel around camping, fly fishing, and driving his truck in the non-summer seasons and recently, him and Charlie were road tripping to see the sandhill crane migration a few states away. He estimated that both he and Charlie have fly fished over 150 rivers in 3.5 years. Captain Coy wanted me to mention that he attributes much of the credit for his adventuring to Charlie.

They’ve spent time as camp hosts in Bannack Ghost Town and throughout the Mission Mountains. When they visited Montana and specifically, the town of Ronan, they knew they wanted to find a place to call their own because it felt “like home”. They currently live outside Ronan in a 111-year-old cabin and they’re working to build other cabins on the property so that they can create a communal living space with other couples. Since October 2018, Montana has been home for Captain Coy and Charlie.


He happened to be buying a new truck back in the summer of 2019 when he learned about the sailing school on Flathead Lake. The guy he was trying to buy the truck from shared that Captain Coy should get in touch with the school and see if they needed any help because summer was fast approaching, and so, he did. He called Go Sail Flathead Lake and just like that, he started working the very next Sunday. He has been working with Go Sail Flathead Lake ever since. He teaches several levels of sail boating on Flathead Lake and said that he “loves it.” He calls himself the “old guy” at the school. He also loves to teach people how to lease sailboats so if you’re ever wanting to lease a sailboat, he’s your guy!


Taking people on the water is a true love of his and he said the best thing is moving the boat “toward the wind with just a sail.” “That’s magic,” he said, and he loves to introduce people to that kind of magic.

He also loves to support people who are looking to buy a sailboat as a kind of mentor. He knows what questions to ask and is happy to support any person with figuring out what sailboat is right for them to make sure it’s a good purchase and a good boat.


On his first day working as a teacher and captain at Go Sail Flathead Lake, Captain Coy’s sailboat motor “crapped out,” and he crashed into the dock. He shared that his goal was to “hit it as easy as possible.” I asked Captain Coy, “how has Go Sail Flathead Lake helped you?” He said, “I learn something every single day,” and that teaching allows him to focus on the technical aspects of sailing, which as he reflected on my question, he then shared that he thought he knew more as a Captain, but he learns something new still, all the time.


He explained how important he thinks it is for people to be allowed to make mistakes. Tiller boats are counterintuitive, and they’re the opposite of what you expect as far as steering the boat goes, so when a person is learning, they need to “get out of their head and feel the boat,” Captain Coy said. Students often forget about the wind and panic, but that’s what Captain Coy enjoys most – supporting students with deep breaths and a positive attitude.

One day when Captain Coy was on the water in the British Virgin Islands, he said he came across a sailboat that had run ashore with 6 attorneys, all very smart people, and they needed help. It was around 3 o’clock in the afternoon, and because sailors have a “help if you can” attitude, he decided to help. Captain Coy could sense that because of the big group, they were adding to each other’s stress, so he suggested that they split up, with some going back to his boat for food and coffee, and then he stayed with the others. The tow boat wound up costing a good amount of money, but the important thing was that everyone was safe. He shared that all kinds of things can go wrong while sailing, such as the line being around the props, running into docks – all kinds of things – and that is why lessons are so important. Nailing the technical aspects of sailing is the key to being a good sailor and setting a good foundation of knowledge.

Sailing takes intuition but it can also be taught. It takes listening and having no preconceived notions or expectations about the sport. It takes showing up with a clear head and an open mind, and for a person to want to learn and be teachable. Internalizing mistakes won’t help, but rather, embracing the lessons with no ego is what Captain Coy stressed.


Captain Coy became a sailor one day when he was sailing in the Channel Islands. He was in a 32-foot sailboat, about 20 miles out at sea, with the wing at 35-40 knots, with the other person aboard seasick, and another crew member too terrified to help man the ship. The wind continued to howl, and the sea continued to become bigger with large swells, 15-18 feet tall, crashing over the boat, and an ever-growing storm. He shared that in those moments, you must decide how to manipulate the boat, what sails to put up, and you must sustain your confidence. His eyelids and hair were covered with salt brine from the sea, but he didn’t get rattled. He remained confident because he said that he had the “skills to do this,” and the “wits of a Captain when everyone else is losing theirs.” The storm lasted 6 hours, and instead of turning back he had decided early on to continue on. When the storm subsided, they anchored the boat and the crew slept for hours, waking up to eat in the evening, and then they went right back to bed.


Sailing is “dangerous,” he said, but it’s “not as hard as you think.” It takes a lot of hard work, many hours of boredom followed by moments of terror with stress and then there are leisurely moments as well. Sailing can be fast, and things can break. It can be an expensive hobby, but it’s a sport that can follow you throughout your life, and it has certainly followed Captain Coy throughout his.


Captain Coy’s favorite place to sail, while a tough question, is the Spanish Virgin Islands. They’re undeveloped and are a grouping of 7 islands east of Puerto Rico. He will sail anywhere as long as his girlfriend, Charlie, is going too. Sailing is just something that he “has to do.” It’s “compelling,” he said, and “always changing.” Once you get the bug, you have to keep sailing – it really is that simple.


When asked what keeps Captain Coy sailing, his answer was a simple one: the “beauty of the water.” He said the water changes every day and he recalled a memory from San Diego that has stayed with him since he witnessed the incredible beauty of the sea. It was the last afternoon he was captaining a sailboat with a couple who was new to sailing, and all the sudden, all around them, were at least 1,000 porpoises. They were “under, next to, and all around the sailboat.” It was a very special moment, he said, and a very special day.


While there may not be porpoises on Flathead Lake, Go Sail Flathead Lake is a special place, with very special people working as instructors and creating a safe environment for people to learn. Captain Coy is intentional with his lessons and cares a great deal about ensuring that people have a positive experience while on the water. You won’t regret spending a day on the lake with him, so if you’re the kind of person that wants to experience something new with an instructor who allows you to take the reins, then you best get to booking a lesson with Captain Coy very soon, because that glorious Montana summer is almost upon us.