Below Deck Sailing Yacht Season 5 Cast — Where Are They Now

Below Deck Sailing Yacht has gotten complicated with all the speculation flying around about what happened to the Season 5 crew after cameras stopped rolling. As someone who has watched this franchise from the very first episode — back when Glenn Shephard was still figuring out how to wrangle a crew that couldn’t fold a napkin straight — I’ve learned everything there is to know about what makes this show tick. Today, I will share it all with you. Season 5 wrapped, the drama settled (mostly), and now the only question anyone seems to care about is where these people actually landed. So, without further ado, let’s dive in.

Captain Glenn Shephard — Still Sailing

Glenn Shephard is probably the most genuinely likable captain this franchise has ever produced. That’s not something I say lightly. The Below Deck universe has churned out some real personalities over the years — not all of them flattering — but Glenn has this rare quality where you actually believe he gives a damn about the people on his boat. That’s what makes him endearing to us longtime viewers.

After Season 5 wrapped aboard the Parsifal III, Glenn stayed active on Instagram — sunrise shots, rigging close-ups, candid crew moments. Normal sailor content. Nothing manufactured for an algorithm. He’s sitting at over 200,000 followers who seem genuinely curious about what he does when the production vans aren’t parked at the marina.

His relationship with Dani Jimenez — chief stew from Season 3, for anyone who needs the reminder — has stayed in the conversation. They confirmed things were real after their respective seasons ended. Glenn, being Glenn, has kept the details close. He’s not doing Instagram Q&As about his love life. What he has done is post enough context for people to connect the dots themselves. Draw your own conclusions.

The Glenn-and-Captain-Sandy dynamic is worth mentioning too. Both have shown up at Bravo events, both have been publicly warm about each other’s work. When Sandy’s crew drama on Mediterranean got genuinely ugly, Glenn said nothing critical. Not a word. That’s just who he is.

Future seasons? He hasn’t confirmed or denied anything. He’s talked about what the show has done for sailing’s visibility — and that visibility is real, honestly — but no signed contracts have been announced publicly. The Parsifal III has been home base for multiple seasons now. The relationship between Glenn and Bravo seems functional. Whether it leads to Season 6 is a different question.

Daisy Kelliher and Gary King — The Ongoing Saga

Probably should have opened with this section, honestly. Daisy and Gary are, for a not-insignificant portion of the audience, the entire reason to keep watching.

But what is the Daisy-Gary situation, exactly? In essence, it’s a years-long push-pull between two people who clearly matter to each other and just as clearly drive each other to the edge. But it’s much more than that — it’s also a case study in how reality TV captures something real and then stretches it across three seasons until the audience is emotionally exhausted along with the people actually living it.

Frustrated by Gary’s Season 4 behavior — pulling both Daisy and Colin Macrae’s girlfriend Sydney Zaruba into his orbit while performing genuine confusion about his own feelings — longtime viewers arrived at Season 5 with low patience and high expectations. Then the trailer dropped. Daisy used the phrase “dead weight” in reference to Gary. That landed hard. Two-plus seasons of defending him, rooting for him, looking visibly tired by him — and then two words that suggested the patience had finally found its floor.

Post-season, Daisy has been traveling, working, and posting content that leans into yachting and lifestyle without the drama-bait some reality personalities use to stay relevant. She is — whatever else — a genuinely skilled chief stew. Her Instagram reflects that. Gary, meanwhile, is posting sailing content, beach shots, occasional throwbacks. He seems fine.

Their current status? Neither party has clarified it definitively. “It’s complicated” is probably the most honest placeholder available. What fans want is resolution. What they’re getting is two people living their lives at a normal social media cadence. Sometimes that’s what reality TV endings actually look like — not a bow, just a fade.

New Crew — Where They Ended Up

Season 5 brought in several new faces. Not all of them made the same impression — on the show or afterward. Here’s the breakdown.

Chef Cloyce Martin

Dragged into the specific pressure cooker that is Below Deck catering — charter guests who paid somewhere north of $150,000 for the week and have opinions about their sea bass — Cloyce arrived with real culinary credentials and confidence that read as competence in some episodes and as arrogance in others, depending on the week. Post-season, he’s returned to private chef work. He’s not chasing the reality TV circuit. His food, by accounts from people who’ve eaten it outside of television production, is excellent. Don’t make my mistake of sleeping on his Instagram — the plating alone is worth a follow.

Davide Morosi

Italian energy, strong deckhand instincts, and a social media following that jumped sharply when the season aired — that’s the Below Deck effect, and it’s as reliable as the tides. Davide has been posting from various locations since filming wrapped, which strongly suggests the yachting work has continued. He’s been warm with castmates publicly. That tells you something about how the experience actually landed for him.

Diana Cruz

Diana came in as a stew with hospitality experience behind her — and it showed. She handled the adjustment period with more composure than a lot of newcomers manage under charter pressure. Post-show, she’s returned to her regular professional life without aggressively building a media brand off the season. That’s its own kind of statement.

Danni Warren

Danni was one of the more talked-about new additions from a viewer engagement standpoint — and she’s handled the post-show attention well. No desperation. She’s stayed connected with castmates publicly, which suggests the bonds formed on the boat weren’t purely performative for camera. I’m apparently more skeptical than most about reality TV friendships, and even I find this one credible.

Keith Allen

Keith’s Season 5 arc had its rough patches. Below Deck doesn’t hide adjustment struggles — if anything, the cameras actively seek them out. Post-season, he’s maintained a lower profile than most of his castmates. Preference or circumstance? Hard to say from the outside. Both are valid.

Emma Crouch

Emma joined later in the season and generated genuine fan interest — not manufactured attention, actual curiosity. Her post-season social media has been consistent without being calculated-feeling. She’s engaged with the Below Deck fan community in ways that suggest she understood what the show could do for her, and she’s kept the tone honest rather than falsely polished. People respond to that.

The broader pattern here is straightforward. New cast member appears on Below Deck, their follower count jumps from 4,000 to 80,000 in three weeks — this isn’t speculation, it’s documented across multiple seasons. Then the real question arrives: what do you do with it? The ones who convert it into continued yachting work, legitimate partnerships, or sustainable hospitality careers look back on the show as a net positive. The ones who chase the spotlight without a plan find it dims faster than expected. Don’t make my mistake of assuming the attention lasts automatically. It doesn’t.

Will There Be a Season 6

Here’s where I’m going to take an actual position instead of hedging endlessly.

Below Deck Sailing Yacht will get a Season 6. I don’t have a Bravo memo in front of me — I have a decade-plus pattern of behavior from a network that knows exactly what it has. Below Deck as a franchise has delivered consistent viewership across multiple spinoffs since 2013. The sailing version specifically has built a devoted audience that distinguishes it from the broader reality TV noise. Bravo doesn’t cancel shows mid-momentum. That’s not their thing.

As of this writing, no official renewal announcement has been made. That’s true. What’s also true is that Season 5’s social media engagement numbers were healthy — the cast was generating conversation, the boat was stunning as always, Glenn is steady, the formula holds. This new iteration took off several years ago and eventually evolved into the appointment television that sailing enthusiasts know and love today.

Cast hints on social media have been appropriately coy. Nobody’s announcing what isn’t theirs to announce. But you can read the warmth — crew members who want to return post nostalgic throwbacks, tag each other, respond to fan renewal questions with smiles rather than silence. That’s not nothing.

Glenn almost certainly comes back if there’s a Season 6. He’s the anchor — literally and otherwise. Daisy and Gary are less certain, purely because their arcs have been so thoroughly explored that Bravo would need to think hard about what new territory actually exists. My read: at least one returns, possibly both, possibly in a dynamic shifted enough to feel genuinely fresh rather than recycled.

I’ve been wrong about reality TV renewals before. I was convinced a certain singing competition was done after a particularly rough season — it ran three more years. So take my confidence with appropriate skepticism. But the bones here are solid. The setting is visually spectacular every single season. The audience for sailing-specific content has only grown since Season 1. A Season 6 announcement feels like when, not if.

Check back here when Bravo makes it official. We’ll have the full cast breakdown ready when they do.