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Sailing Story: Dave Shafer

Go Sail Virgin Islands ASA courseSailing Story: Dave Shafer

Dave Shafer isn’t quite sure where his sailing story starts. On the one hand, you could say it started when he was a teenager living in Appalachia. 


“I was on a very small lake on— I don’t even know if you want to call it a sailboat, it was a 2x4s with a sail on it,” he laughed. “It was something we threw in the back of the pick up truck, took to the lake and said, ‘look we’re sailors!’”


His days on a cobbled together sailboat didn’t provide much inspiration to kick start his love of sailing. “It never really interested me much because I was into powerboats,” he explained. “ But I grew up on water and in any given week, even to this day, 3-4 days a week, I’m out on the water somehow.” 


However, as Dave got older, the idea of sailing reentered his mind. He decided that sailing in the BVI would be a great way to spend his honeymoon with his new wife.  Unfortunately, that would prove to be another false start to Dave’s eventual love of sailing. 


“My honeymoon in 2010 was beyond a disaster for a charter,” he explained. “The ‘captain’– I say that in parenthesis—we found out it was his first time captaining a charter.” Not only that but the first night aboard they had no water, no A/C, and boiled in a bay with no breeze to cool them down. 

“That’s how I spent the first night of my marriage, and from there it all went downhill,” he laughed.

Luckily, rather than give up on sailing completely, Dave decided to just do better research into which sailing companies to book with. 

After his honeymoon mishap, Dave developed a keen eye for finding reliable charter companies in the Virgin Islands. This eventually led him to Go Sail Virgin Islands, where he booked a Cruising Couples Catamaran Course’. The boat was not full but they took us on the trip anyway and we ended up on a private trip. I was glorious! 

“The rest is flat out perfect history,” he said. He found himself immediately clicking with Go Sail Virgin Islands’ Captain Trevon and admiring him as both a captain and an instructor.


“That guy is as laid back as it comes— he just gets it,” he explained. “When you are wrong he doesn’t put you down. Even if you screw up, he doesn’t put you down. He makes you think about it, why do we do it this way?”


That instant connection between captain and crewmember, instructor and student, has now paved the way for a strong friendship. “I have introduced him to people as this is my guy, this is my skipper!” 

This coming year, Dave looks forward not only to sailing with Trevon in the Virgin Islands again but also meeting him in Montana for a sailing trip on Flathead Lake. 

Dave’s sailing story is proof that even if the start to your sailing story isn’t pretty— it can still end up being everything you’d dreamed it would be and more!