Captain Glenn Shares Advice for Breaking Into the Industry: "Go Where the Boats Are!"

21 February 2022 By Holly Overton

Holly is the editor of Dockwalk. She grew up racing sailboats in England before switching to the world of superyachts and moving across the pond to Fort Lauderdale.

As S/Y Parsifal III sails onto screens for the third season of Below Deck Sailing Yacht, Dockwalk catches up with Captain Glenn in a rare moment of downtime as he shares his route to the wheelhouse and tips for getting hired…

Captain Glenn Shephard had been at the helm of the 54-meter Perini Navi Parsifal III for over a decade when he found himself as frontman of Below Deck Sailing Yacht. Producers were struggling to find a yacht that would fit their new sail-powered spin-off when Captain Glenn’s name was thrown into the ring. With 22 years of experience in the industry and a network of over 300 sailing yacht captains, if he didn't know of a suitable boat then he would certainly know someone who did. As it happened, Parsifal III was up for sale at the time and so he pitched the idea to her owner.

Captain Glenn started on board Parsifal III which morphed into a rotation and eventually a full-time position. He has now been the captain for 12 years.

“I wasn’t sure at first that I wanted to be the captain. I hadn’t seen Below Deck but after speaking to people and understanding how it worked I thought, okay, why not?" says Captain Glenn. "The first couple days of having cameras on you while you're is a bit weird, but you quickly forget that they're there and just go on with doing your job.”

Captain Glenn was born in Montreal, Canada, but calls Palma, Mallorca, home. Even when he's off rotation you will find him cruising the Mediterranean where he keeps a 42-foot Jeanneau. “That’s why I got into superyachts, because of my love for sailing. There is a certain group of people in superyachting who only want to work on sailboats and I’m one of them."

For Captain Glenn it all started with a backpacking trip in the 1980s. “I bumped into a guy in Rome who had a 50-foot motorsailer and I ended up spending almost a year on that boat cruising around. That’s what got me hooked”

Like most budding yachties he went to Fort Lauderdale and began dockwalking in an attempt to land his first job. "Back then it [superyachting] wasn’t the same as it now - today it's a lot bigger - but I figured I’d give it a try." After nine months scrubbing decks on a motor yacht he found himself in Monaco where he picked up his first sailing superyacht gig as a deckhand on board the 53-meter Perini Navi Atmosphere. From there he moved to first mate on the 77.6-meter Mirabella V (now M5), the world’s largest sloop-rigged sailing yacht, as well as her sistership Mirabella IIIbefore finally arriving on Parsifal III in 2008. It started as a relief job that morphed into a rotation and eventually a full-time position.

“Save some money and go where the boats are! Fort Lauderdale, Newport, Antibes, Palma, Antigua - that’s where you’re going to get the job,” says Captain Glenn

“One thing I really love is inspiring new people to come into the industry,” says Captain Glenn. It was one of the reasons he decided to take the Below Deck captaincy. “I like the fact that people who don’t know how superyachts work get a chance to peek inside this crazy world and see what it’s like for guests but also for the crew.”

“People who work on superyachts aren’t really cut out for work in a cubicle in a corporate job. They are more adventurous and need that change of scenery and I think it is nice that people can see that and think ‘oh, there’s another career possible.’ I hope it inspires young people to give it a shot.”

And, according to Captain Glenn, it is not as hard as you might think to get a foot in the door. “You have to save some money and go where the boats are! Fort Lauderdale, Newport, Antibes, Palma, Antigua — that’s where you’re going to get the job. You could get lucky, and it could be a couple of weeks but it could take a couple of months."


He explains that most captains will be hesitant to hire entry-level crew from a CV alone so wannabe crew will need to hit the docks and get networking. “One of the best ways to get some experience without having to commit for a full-time live-aboard job is dockwalking and day work. Talking to somebody over the phone you don't really get that sense of that person, but if you work on their boat cleaning bilges or scrubbing decks for a week, they're really going to have a sense of who you are. And that's going to help you get your foot in the door."

Once you've secured that first job his next piece of advice is to stay put and get a year on your first boat before moving on. “If you have a year on your first boat you won’t have to dockwalk anymore. A captain will see your CV and if you were in a position for a year and didn't get fired, you’ve got to be doing something right.” Once you have those first six months to a year on the resume it becomes a lot easier to get your next job and both captains and recruiters will be more likely to hire you over the phone.

Of course, it is easy to be seduced by Below Deck where thousands of hours of hard work are condensed into just 16 hour-long episodes. “When we're not on charter, it's eight to five and sometimes you'll have weekends free. But when you're on charter, it's 16 hour days and you can go a month without having a day off," says Captain Glenn. “And I’m no spring chicken anymore. I want to slow down a little bit, smell the roses, and do more cruising on my boat,” he says, which is why he now captains Parsifal III on rotation.

Below Deck Sailing Yacht season three takes place on home turf for Captain Glenn in Spain and premieres on February 21. He will be joined by returning cast members Gary King and Daisy Kelliher as well as some new faces. “Below Deck Sailing Yacht is a little bit more fun. It’s not just a floating five-star hotel and I think a lot of people dig that. There's obviously some drama, some excitement, and a lot of sailing. And of course the crew make it very interesting," says Captain Glenn.


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