‘Below Deck Sailing Yacht’ Captain Glenn Shephard Dishes on Season 5 Dramas, Daisy & More

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Captain Glenn Shephard has fired up the Parsifal III for Season 5 of Below Deck Sailing Yacht. The hit show returned October 7 with Chief Stew Daisy Kelliher, First Mate Gary King and the rest of the crew chartering in the Spanish party island of Ibiza.

Rounding out the team are Chef Cloyce Martin, Chief Engineer Davide Morosi, stews Diana Cruz and Danni Warren, and deckhands Keith Allen and Emma Crouch. Shephard once again has his hands full managing the personalities and keeping the vessel on course. Here Shephard dishes on the challenges he’ll face this season.

Given the history between Daisy and Gary over the years and what transpired between the two in the past, did you approach this season any differently?

Glenn Shephard: I knew there would be some leftover feelings from last season, but I also know they are adults and find a way to put that aside. All I’ve ever seen from them is professionalism. That’s what I counted on. Of course, they will chat about it but also get on with doing their jobs. They know that’s why they are there.

How did Ibiza compare to other destinations?

I live one island over, which is Palma, Mallorca, which is 60 miles from Ibiza. I’ve been there before. I’m on my little boat right now. I’ve had this boat over there. It’s a great cruising destination, especially because you have two islands. You have Ibiza and Formentera, you have waters there like the Caribbean. It’s beautiful. What Ibiza is known for is being a party place. Anybody who wants to party, that is where you’re headed in the summer. They have all these big clubs, it’s a jet-set kind of place. A beautiful setting as well.

How does that play into the season in terms of the guests?

You can guess if you’re going to Ibiza and people are coming for a holiday, there are going to be clubs involved. There will be day clubs and partying, but also night clubs. They go quite late, which is a challenge because you have to do pickups. If you’re at anchor, you have to go pick them up in the middle of the night. That’s an extra challenge, but it’s not something we haven’t done in our careers. We know how it works and make it work. We know there is a lot of partying. On the boat and off the boat. It can be a crazy place to be for sure.

Key Art — (Photo by: Bravo Media)

Any guests you have to step in and lay down the law?

Guests get crazy, but I don’t think anyone gets aggro.

What kind of work was done on Parsifal III after last season?

It’s a night and day difference. What we had happen last season was rare. It had nothing to do with neglect or lack of maintenance. It was a part of the engine we did work on. It was tested and supposed to be perfect. It turned out it failed. It almost cost us the whole season. In light of that, as soon as we were done with the last season we didn’t go back to the Caribbean.

We spent the whole winter rebuilding the whole engine. Every part that you can unbolt and unscrew was taken off and a new part was put on. It’s basically a new engine. We did a lot of work besides that. We did some work in the galley, added new appliances, worked in the engine room, and worked on generators, water makers, and all the different systems. The big difference is we have a reliable engine now. We didn’t want to take a chance of that happening again.

One thing about this show is you always have a cabin mate. How does this year’s cabin mate work out for you?

I’ve been on that boat for 15 years. In season, I’m always sharing a cabin. My philosophy is I’d much rather have that extra crew member sleeping in that bunk above me to help run the boat when we’re busy than to have a cabin to myself. In between seasons when we drop a couple of crew, I usually kick them out. Half the year I have my own cabin. When you see me on the show, I’m always sharing.

There were some challenges there, especially with the kids when they had so much to drink and stumbling around the cabin, falling down off the bunk on top of me, and placing things on my head. I saw in the trailer Davide jumping into the bed naked. I didn’t know he did that. I saw that on the trailer as you saw it. I think if I saw that happening I would have been like, “Dude, put something on. It’s not a locker room.” You get so busy in season, that you just go in to sleep in there. So it’s not a big deal.

Below Deck Captains – Lee Rosbach, Sandy Yawn, Glenn Shephard, Jason Chambers, Kerry Titheradge (Bravo)

How would you describe the crew dynamic this season?

It’s a great crew. We have a few incidents where things could have gone a lot better than they did, without giving too much away. I did have to crack the whip because some people stepped out of line. I try to give them a little bit of space, but I don’t want to deal with people who give an inch and they take a mile. That’s a problem and when I have to put them in their place. You see a little bit of that this season. Mostly, I would say it’s a great group of people. We meet our challenges and get past them. I think it was a successful season.

There seem to be some issues between Cloyce and Daisy. You have a front-row seat to this early on.

I’m always trying to keep an eye on that relationship and the galley itself. Making sure the guests’ needs are met and the food is going out in a timely manner and presented correctly. We definitely have some challenges this season. There are some things you’ll see progress. It’s not all smooth sailing.

Related‘Below Deck Med’ Captain Sandy Yawn Talks Married Life & Season 9 Finale

What kind of friendship and bond do you have with your fellow Below Deck captains? Is there a group chat?

We’re pretty good friends. We usually meet up at events, especially BravoCon. I’m pretty close with Sandy [Yawn]. I’d like to spend more time with Lee [Rosbach], but we don’t meet up that often. I’m very close with Kerry [Titheradge]. We hang out a lot. I think he is a great guy. We kind of have a running joke that we kind of look the same. I have a little more hair than he does though. When we were at the last BravoCon. I was already in the convention center. He came in saying he had just got out of the black SUV and there were fans behind the barricades. Someone screamed, “We love you, Captain Glenn!”

He comes in and tells me. From then on, it’s a running joke that we are each other’s mini-me or stunt double. I guess we look a little similar. It happens, so we get a laugh. I don’t see Jason [Chambers] as much because he is halfway around the world. I meet up with him at BravoCon too, and we have a blast. They are all great people. I feel very fortunate. I love it. The thing about it is this is my normal job. What you see me doing on the show is exactly what I’ve been donig for the past 15 years.

Below Deck Sailing Yacht Season 5 premiere, October 7, 9/8c, Bravo

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