Below Deck Sailing YachtCaptain Glenn teases
Published on December 01, 2025 EDT

Captain Glenn Shephard teases some "pretty hairy stuff" on Below Deck Sailing Yacht season 5, which includes a possible collision and crew shenanigans that turn "potentially dangerous."

The season 5 trailer shows Parsifal III coming too close for comfort with another sailing vessel in the dead of night. Cameras capture first officer Gary King scrambling as the crew rushes to prevent disaster: "That boat is getting close," he observes.

Captain Glenn explains to Entertainment Weekly how the sailing yacht encounters either a near miss or a collision due to some inclement weather.

"When the weather's bad and people expect it, they take precautions," Captain Glenn says. "It's thunderstorms, which are what catches people off guard." He recalls a recent storm that beached "a lot of boats." Adding that many boat crashes result from unexpected bad weather.

Fred Jagueneau/Bravo via Getty

During season 3's weather-related near catastrophe, deckhand Tom Pearson was blamed for his slow response during late night anchor watch. He waited to wake up Captain Glenn and Gary until the sailing yacht was in peril. Thankfully the crew narrowly managed to avoid disaster and Tom was fired.

This time is different. "I was very impressed because the weather wasn't so great," he says of how his deck team reacts. "We have an issue with another boat. There's almost a collision. Maybe there's a collision, I'm not going to say."

While he was impressed with how the deck team reacts to the situation, he wasn't impressed with the crew's behavior this season. "You guys went out with the guests," Captain Glenn is heard telling the crew in the season 5 trailer. "I set some ground rules, two drinks maximum."

Whatever ground rules Captain Glenn set, the crew clearly breaks them. In one scene in the trailer the crew is seen drunkenly running around the boat, chief engineer Davide Morosi's face is cut and bleeding – all over the white banquet couch.

Fred Jagueneau/Bravo via Getty

Furious as he wakes to the aftermath, Captain Glenn drags the crew from their bunks to face the consequences – which he says were very serious. "Absolutely dangerous, silly, dangerous, but also creating hard work that we don't have time for," he tells EW of the crew's behavior. "So yeah, quite serious. And I try to get the point across that cannot happen again."

Gary seems to have something to do with Davide's bleeding face as his name is heard being called in the trailer as Davide walks away laughing (and bleeding). Captain Glenn says while Gary has grown through the years, he's not there quite yet.

"I've seen a lot of progress, and I've seen Gary growing up," Captain Glenn says. "He's trying to move forward, but I also see him doing silly things, so he's not quite there yet. I definitely saw progress, but I guess you see a couple relapses and he's just up to silly stuff. I think he realizes though it's time for him to grow up."

Captain Glenn is also seen possibly firing someone this season too. "Somebody might be walking the plank," he teases.

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Below Deck Sailing Yacht airs Mondays at 9 p.m. ET/PT on Bravo.

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