Below Deck Sailing Yacht’s Captain Glenn Shephard Tells STELLAR His Wildest Guest Encounter And How To Get A Job In A Crew

Calling all Yachties!

Below Deck Sailing Yacht is back with season four and after a rocky start to the season there’s a lot more to come.

STELLAR got to chat to Captain Glenn Shephard (yes, he’s as sweet in real life) to talk all things boats, drama and celebrity guests.

Hi Captain Glenn! How are you feeling about S4?

I think it’s going to be another really good season. We have the dream team back, Gary, Daisy, Colin, we’ve started off with a few hiccups, but things are looking up. We have some amazing guests and beautiful destinations.

BELOW DECK SAILING YACHT — Season:4 — Pictured: Captain Glen Shephard — (Photo by: Fred Jagueneau/Bravo)

There’s a bit of drama and romance between the crew, do you like hearing about it?

When I’m not in the scene that means I’m not there, I’m not privy to it, and sometimes I only see it months later when it’s on air. But obviously I hear stuff, I have an idea what’s going on, but I try to stay out of that and I expect those guys to be professional about it, but romances happen. People working closely together, they’re working really hard, they need to blow off a little pressure in between charters and sometimes this happens.  

We all live on the same boat and I am the boss, but they have to have their own life and once it doesn’t impact the quality of service that we’re giving the guests, I purposely try to stay out of it. If it got crazy that’s different, if we had two crew members that were in a relationship and were fighting in front of the other crew members or God forbid in front of the guests, that’s when I would step in. 

As long as the guests don’t have any clue of what’s going on there, then they’re doing their jobs well and what they do on their free time is pretty much for them. 

BELOW DECK SAILING YACHT — Season:4 — Pictured: Daisy Kelliher — (Photo by: Fred Jagueneau/Bravo)

Speaking of the crew… Daisy is Irish! Have you picked up anything Irish off her and have you ever been?

A little bit of Daisy’s Irishness has rubbed off I suppose. I did have 24 hours in Dublin and I went around Trinity college and had a look around and I loved it,  it was amazing. I do want to go back and visit the countryside and spend some time there. 

Watching the show, people might be interested in a job like that. Have you any tips for those wanting a start?

I actually have a little Facebook group called Big Sailboat Jobs where I help boats find crew. If people want to reach out to me directly, I’ll give them some pointers.

But the most important thing I think is you have to get the basic safety and health certificate and then save some money to support yourself, go where the boats are (Fort Lauderdale, St. Maarten, Palma de Mallorca). Try to find day work, which is non-liveaboard work.

Boats get to know what you’re like and often they’ll offer people a job. That’s the way to break into the industry.

What has been your wildest guest experience during your career?

Years and years ago when I was an anchor watch person I wasn’t a captain, and when I went to do my midnight ‘dogwatch’ we were in the Caribbean and the guests insisted that the crew partied with them.  

And everybody except myself was partying really hard, it was getting to the point where things were getting out of hand and then they all went to bed, in their own cabins, and I got stuck with cleaning up all the mess.

Would that be allowed on your boat?

We’ll eat dinner with the guests whatever makes them happy, but we can’t be drinking, we have safety responsibilities so we can’t party with the guests it’s not appropriate.

Who would your dream guest charter be dead or alive?

Albert Einstein, Mick Jagger, Paul McCartney, Rod Stewart, the list is endless. 

All good choices… Who would you like to play you in a movie of your life?

Pauly Shore, I think I look a little bit like Pauly shore if anyone remembers him from the MTV days. Or Brad Pitt, Matt Damon, whoever! 

Do you have any celebrity fans?

I don’t want to name names. In the industry we meet celebrities quite regularly because they charter boats or come as guests. But we don’t generally speak about them or say their names, it’s kind of meant to stay discrete. But yes, I’ve definitely had a couple of celebrities follow me.

Finally, how would you describe S4?

Hold on to your hat! It’s going to be a wild season there’s still some pretty crazy stuff coming. I think people are really going to enjoy it.

The brand new season is available to stream on Hayu now!

• below deck
• Captain Glenn Shephard