5 Memorable ‘Below Deck’ Charter Guest Hookups

Not all Below Deck charter guests leave the superyacht with just a sunburn and a fully belly. A few end up making a “love” connection with the crew, sometimes on charter.

Below Deck Mediterranean second stew Kyle Viljoen openly flirted with charter guest Frank Fay, then they exchanged a passionate kiss, but only after Fay’s charter ended. Deckhand Courtney Veale recently told Showbiz Cheat Sheet she didn’t think crew should ever cross the line with guests.

Stew Kyle Viljoen kissed a 'Below Deck Med' charter guest. He sits at a table with crew.
Kyle Viljoen | Laurent Basset/Bravo

“In the past, I’ve always thought kind of guests were off limits,” she said. But added that as long as the kiss didn’t happen on charter, it should be OK.

So who else has hooked up with a charter guest (sometimes on charter)?

Bobby Giancola kissed a guest on a ‘Below Deck Med’ charter

Deckhand Bobby Giancola was busted in a liplock with a Below Deck Med charter guest during season 2 when he “escorted her” on a jetski. Giancola actually matched with the guest on a dating app and the primary thought it was amusing they had a connection.

Kissing a charter guest while on charter is definitely a violation. But, at the time, Giancola wasn’t too concerned. “Coming into this season with romances, I wasn’t looking for one. I just wanted to learn my job better, solidify my job in the career of yachting,” he told Bravo’s The Daily Dish. “But sure enough, there’s gonna be pretty girls on the boat.”

Did Hannah Ferrier cross the line with a guest?

While Giancola was caught on camera kissing the guest, chief stew Hannah Ferrier had a quick kiss with a charter guest behind the scenes during the same season. Ferrier and charter guest Jason Ziegler had instant chemistry and ended up texting one another while on charter.

But one questionable scene showed Ferrier following Ziegler into his room (to ask him a question). Audio made it sound like Ferrier and Ziegler made out. She said it was only a quick kiss. Still …

“It was definitely a case of the angel on one shoulder and devil on the other. Despite the obvious chemistry and flirting, once he actually kissed me, I had a realization that this needed to wait until after he had left the boat. So in short – a very quick kiss!” she wrote in a Bravo blog.  

Culver Bradbury kissed a guest kissed at the bar

Deckhand Culver Bradbury exchanged a passionate kiss with charter guest Jourdi Bleu at a bar after her Below Deck Down Under charter ended. In this case, the kiss wasn’t the biggest scandal, but rather a surprise to deckhand Brittini Burton.

Burton and Bradbury planned to embark upon a road trip after the season ended and were flirting on deck. But Burton said the kiss wasn’t a big deal. Plus chief stew Aesha Scott explained that what Bradbury did wasn’t wrong when it came to crossing the line in yachting.

“You know, it’s free rein and they’re all adults,” she told Showbiz Cheat Sheet. “They can do what they want. On the boat, you really shouldn’t do that. But if they want to give you their number and you have a little cheeky kiss afterward, then go for it.”

Ashton Pienaar kissed charter guest Molly at a club on ‘Below Deck’

Bosun Ashton Pienaar spent plenty of time flirting with model Molly O’Connell on Below Deck Season 7. But he “went for it” at a club after O’Connell’s charter ended. “They stayed for a few days. We spent a few days with them,” he said on the Below Deck After Show. “What an awesome time we had with those two girls. It was really, really fun.”

Pienaar wasn’t the only one who made a “love” connection on that charter. Deckhand Tanner Sterback had a connection with Below Deck charter guest Justine Dorae Vastano, the private chef who gave chef Kevin Dobson a hard time. Sterback enjoyed hanging out with Vastano so much at the club, that he visited her when he got home.

“She is a very good chef. She’s cooked for me,” he dished. “I visited her in Charleston and stuff like that, so we had some fun. It’s so simple, but she cooked me the best avocado toast and breakfast in bed. F***ing hell, it was great.”

Danny from ‘Below Deck Med’ falls for a charter guest

Deckhand Danny Zureikat wore his heart on his sleeve on the first season of Below Deck Med. When the models from Tilted Kilt did a photo shoot aboard the Ionian Princess, model Morgan caught his eye.

In addition to flirting with Morgan, Zureikat passed her a note and got way too personal with her. Captain Mark Howard warned him to stop flirting with the guests. But Zureikat didn’t care – he was in love. During a beach shoot, Zureikat held and kissed Morgan while the other crew members worked in the hot sun.

For his part, Zureikat regrets nothing. “People do the craziest things in the pursuit of happiness,” he told Bravo. “To me there is no higher form of happiness than love, yet so few actually find it. If a person feels like there is even a slight chance that they have found their soul-mate, then I feel like any actions are justified considering what’s at stake. Moreover, people will always regret what they didn’t do more than what they did. Nothing haunts us like the things we don’t do, so stop the “what ifs” and begin to pursue. For those reasons I don’t regret building a relationship with Morgan; she is an amazing person. That being said, I would go about connecting with Morgan in a completely different way, and it would not have taken place in a work environment.”

Zureikat was later fired.

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