Below Deck Sailing Yacht OG star Captain Glenn Shephard was the only surviving cast member called back to continue to helm Parsifal III after a lackluster inaugural season. Since then, the laidback, kind, incredibly personable personality of Captain Glenn has won over a throng of Below Deck fans. Twitter and Reddit routinely show him as the most beloved captain working in the Bravo’s reality TV yachting franchise, especially after Captain Lee Rosbach wasn’t invited back for Below Deck season 11. Captain Glenn continues to deliver on his quirkiness and funny one-liners on Below Deck Sailing Yacht season 4, but there’s a lot more depth to this reality TV star than revealed on the show. Here’s everything fans need to know about Captain Glenn.
Captain Glenn: Family, Girlfriend, Friends, Nationality, Travel, Age, Birthday, Height
Before working in the yachting industry, Captain Glenn lived in Hong Kong, Australia, Tokyo for five years, and all over Europe. He originally grew up in Montreal, Canada. The Canadian reality TV star recently returned to his home province of Quebec, and it appears he grew up in a neighborhood off the island of Montreal, in Saint-Lazare, Quebec. Captain Glenn’s slight accent when he speaks English is most likely because he grew up in the French Canadian province. He’s likely bilingual, speaking French, which would help him when he travels Paris and the rest of France, as long as the French can understand his Quebecois accent that is.
Glenn grew up in Quebec, but part of his family is from Nova Scotia, a Canadian province on the east coast known for sailing. It’s also where the famous Bluenose schooner was built and raced, which is on the Canadian dime (a Canadian coin).
When Glenn left home he became a Canadian expat, traveling and working all over the globe. He currently calls Palma, Spain, his homebase, where he has an apartment. It’s also Parsifal III’s home harbor. However, Glenn has his own sailboat, Avalon, which is his traveling apartment for the months in the year when he’s not on the clock.
At the end of 2022, Shephard revealed he had someone special in his life. Since BDSY season 1, fans wondered why Captain Glenn had a picture of a mystery woman in his cabin. It turns out he’s been dating a gorgeous Puerto Rican, Danelis “Dani” Jimenez the past five years. The two travel the world and share cute pictures together as a power couple.
“Now that I’ve got a lot more free time we’re able to spend most of our time together, mostly cruising on our little boat Avalon and when the weather is cold, traveling,” Shephard said on his Instagram.
Danelis doesn’t speak much English, so Captain Glenn communicates with her in “bastardized” Spanish.
Captain Glenn’s birthday is reportedly on July 15, and he’s currently age 63. He’s going to turn 64 in the summer of 2023. Glenn’s zodiac sign is cancer, which makes sense since he’s a leader with a strong intuition of how to get the best out of his crew. Captain Glenn’s height is around 5’5″ because he stands a couple of inches shorter than his first officer.
Gregarious Captain Glenn has also made a boatload of friends over the years. He considers many of his crewmembers to be like family, including some of his Below Deck Sailing Yacht cast members.
Captain Glenn: BDSY Job, Previous Yachting Work
Captain Glenn was backpacking in the 80s in Europe when he met a guy in Rome and worked on a boat as an unpaid deckhand for a summer, he told the host of the So Bad It’s Good podcast.
The captain of Parsifal III for 13 years, Shephard worked his way up the chain of command starting at the age of 41! In 2000, Captain Glenn decided he wanted to pursue a career working on sailing superyachts. Sailing his own small sailboat for the better part of a decade prior, and falling in love with it, he thought it could be a dream job, working on the open seas, while making lots of money to prepare for retirement.
“In 2000 I went cruising on my boat around Greece, kind of same area where I am now. And I thought, okay, I’ve got all my ducks in a row. I’m going to go try this thing. So I put my boat away in Greece, flew back to North America, went and borrowed my dad’s campervan [in Canada], drove down to Fort Lauderdale… My cousin was living there, he got me into a crew house… he gave me some pointers how the industry worked from a working standpoint. And my first gig was working at the boat show in Fort Lauderdale in October 2000,” Captain Glenn said on The Ocean Cruisers podcast.
His first job was cleaning boats at 4:30 AM each morning.
“And from there I ended up getting a long-term day work job on Big Eagle, which was a well-known boat back then. And from there I got another day work job on Christiansen, which was a 38-meter motor yacht,” Captain Glenn continued. His captain eventually hired him but it was the only motor yacht he’d ever end up working on.
Captain Glenn did an Atlantic crossing in that superyacht and ended up in Monaco. He left working on that boat and ended up as a deckhand in the Mediterranean, working their for five years, while getting more yacht training. He learned the ropes and then was hired as first officer and relief captain on sailing superyacht Mirabella V, the biggest single-masted sailing superyacht in the world.
Eventually an old captain on a sailing superyacht had quit, and the new replacement captain quit, too. Captain Glenn jumped at the chance to become a full-time superyacht captain and rushed back to Europe to take the job.
A few years after that, Captain Glenn began working on 45,000-liters-of-gas-engine Parsifal III and has been there the past thirteen years. He now works half the year on the ship, working with good friend and co-star Gary King, the ship’s first officer throughout the year.
Captain Glenn’s Sailboat, Lifestyle, Leadership Style & Below Deck Sailing Yacht Season 5
“People think I’m crazy, you know. A lot of people who work on boats, that’s the last thing they want to do on their time off. But for me, I love it,” Captain Glenn said on The Ocean Cruisers.
Shephard owns a Jeanneau 42-foot DS sailboat he bought brand new in 2008 and launched the boat in 2010, naming her Avalon. He still owned his first boat, a 34-foot Jeanneau he was sailing in the Caribbeans in his spare time.
Huge Mediterranean storm, Gloria, damaged Avalon by beaching her and crashing her into rocks. But he got insurance money and had someone fix the fiberglass on the boat to restore her integrity.
Glenn’s boat has two cabins so he can have family visit him, including his nephews.
“I love my apartment [in Palma, Spain]. [But it’s] the same place. Every time I come here I’m in exactly the same place. Where as on my boat I can take it to Istanbul, or I can take it to Mykonos, or Santorini, or Capri, so it’s a floating apartment for me. That’s why I love it. I can travel and have all my stuff with me.”
Despite Shephard not exactly being a landlubber, he’s buying a “land yacht” i.e. RV in the next year or two to travel Europe on the open road with his girlfriend. In the meantime, he enjoys driving his two BMW sportscars.
“Plan in the fall is to do some of Turkey, more of Greece. Next summer will be Montenegro and Croatia, maybe take it up into Venice. And then I’m thinking about heading west.” He also has plans to sail the Pacific Ocean in his retirement.
When Captain Glenn isn’t navigating around the world, he also enjoys fishing, golfing, snowboarding and sightseeing. He loves learning about history, culture, food, and meeting new people. The perpetual globetrotter and raconteur could give the Dos Equis a run for his money as the most interesting man in the world.
Captain Glenn: How He Became Famous, BDSY Season 5, Influencer Sponsorships & Future Book
Glenn thought he’d never be on TV before he was cast on Bravo’s BDSY. Season 4 charter guests and podcast co-hosts Justin Guarini and Kim Phillips asked Captain Glenn what he enjoyed most from doing the show. “Getting recognized by people who see the show, connect with the show… I love meeting people and I love people who’ve seen the show. And just chatting with them.”
In a recent interview on The Big BOAT Interview podcast, Captain Glenn said, “Honestly I wasn’t sure I wanted to be involved. But looking back, I’m really glad I did it. It’s such a cool experience to see how they make this show. You wouldn’t believe what goes into it.” He went on to explain how he was contacted by Below Deck show producers. They wanted him to put them in contact with captains and a sailing superyacht available to film the show. He put them in touch with the owner of Parsifal III and the producers then asked him if he’d star on the show.
Now it looks like it’s all but confirmed Captain Glenn will star on Below Deck Sailing Yacht season 5. Bravo hasn’t yet officially announced greenlighting season 5, however Captain Glenn and Chief Engineer Colin MacRae recently met up with a show producer and show is a hit. On top of that, Captain Glenn mentioned on the So Bad It’s Good podcast he’d be back working on Parsifal III in June 2023. Previous charter seasons of BDSY filmed in the summer the past four years consecutively.
Shephard also said in multiple interviews he’s looking into writing a book about his life. Captain Lee previously wrote an autobiography called Running Against the Tide and Below Deck Mediterranean Captain Sandy Yawn’s book, Be The Calm Or Be The Storm, a book based on her life experience.
In the meantime, Colin’s trying to get Captain Glenn to start in own YouTube vlog channel. Although Captain Glenn isn’t yet making many videos, he’s gotten over being camera shy and now posts selfies of all the cool places he visits around the world. He’s also cashing in on sponsorship endorsements on his Instagram. Below Deck fans would certainly watch more videos by Captain Glenn, like the one he did on his favorite Mediterranean bread snack.
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