‘Below Deck’s 8 Worst Guests Of All-Time: From Jill Zarin To Delores The Midnight Swimmer

Demanding charter guests are a given while working on a mega-yacht — and the various Below Deck crews over the years have certainly experienced their fair share of them. Whether it’s Jill Zarin requesting special ice for her Diet Cokes or Timothy Sykes retracting a portion of the crew’s tip right in front of Captain Lee Rosbach , the yachties are always in for some kind of treat — or headache.

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In the 11 seasons of Below Deck, nine seasons of Below Deck Mediterranean , four seasons of Below Deck Sailing Yacht and two seasons of Below Deck Down Under , Captain Lee, Captain Sandy Yawn , Captain Kerry Titheradge , Captain Glenn Shephard , Captain Jason Chambers and their staffs have encountered plenty of high-maintenance guests aboard their respective vessels.

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We somehow managed to pick a handful of guests who have infamously given the crew members a run for their money — but let it be known that it was no easy task to narrow down the abundant slate of finicky charters.

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Aside from the ones we previously mentioned, we can’t forget the time lawyer Erica Rose and her husband caused quite the splash on Below Deck Sailing Yacht with their obnoxious and combative criticism of the chef’s food. Or when Below Deck chef Rachel Hargrove was forced to concoct blended versions of each meal (lobster included) to appease a recently injured woman who had her jaw wired shut.

In case you need more of a refresher, we gathered a roundup of eight of the most difficult charter guests in Below Deck history. Check them out below!

• Jill Zarin ( Below Deck Season 11, Episode 9)

  

  The Below Deck crew was just about ready to make Jill Zarin walk the plank when she appeared as a guest of the primary in a Season 11 episode. The Real Housewives of New York City alum had the interior team frazzled as she complained about everything from the food to the lack of toiletry baskets in each cabin. She even suggested that chief stew Fraser Olender purchase a button so she could call on him any time she had a request. And it bears repeating that she wasn’t even the primary guest!

  Barbie Pascual described Zarin as a “freeloading guest who’s extremely demanding,” while Olender said, “Jill is crawling into my brain and eating away at my soul.”

• Delores ( Below Deck Season 8, Episode 11)

  

  Captain Lee was heated when guest Delores defied his commands and drunkenly jumped into the water in the middle of the night. The Below Deck icon told the primary guests that their “charter [was] over,” before forcing his crew to stand guard outside Delores’ room to make sure she didn’t come out again. “First thing in the morning, I’ll drag everybody’s ass back to the dock and kick their ass to the curb,” he said in his confessional. “We’re not taking those risks. Not on my boat.”

  The next morning, Lee allowed the primaries to remain on the yacht as long as they sent Delores packing.

• Erica Rose and Charles Sanders ( Below Deck Sailing Yacht Season 3, Episode 4)

  

  American lawyer Erica Rose and her obnoxious husband Charles Sanders were one of the worst primaries the Below Deck franchise has encountered to date. During their stay on the sailing yacht, Sanders aggressively complained about his food, claiming McDonald’s could’ve served a better omelet than the high-end chef on board. He also bickered with their fellow guests, nearly causing a physical fight when he referred to his friend’s wife as a “bitch.” Plus, someone stained the $50,000 white couch with tan body makeup. And just when everyone thought things couldn’t get any worse, they left an insultingly low tip ($6,500, to be exact) for the entire crew to split.

• Timothy Sykes ( Below Deck Season 2, Episode 10)

  

  Even Captain Lee remembers Timothy Sykes as the worst charter guest he’s ever dealt with. Sykes, a 32-year-old entrepreneur who wears shirts with his own name on them, flew to the dock via helicopter with his 19-year-old girlfriend. After spending most of his trip complaining about the yacht’s internet issues and chef Ben Robinson’s food, he infamously deducted $5,000 off the tip, which was initially a whopping $22,000.

• Chelsea ( Below Deck Season 9, Episode 9)

  

  Chef Rachel Hargrove had her work cut out for her when one of the primary guests in Below Deck Season 9, Episode 9 came onboard with her jaw wired shut. Chelsea, who had recently suffered a bicycle accident, had multiple “meltdowns” when her liquified food did not come out at the same time as everyone else’s meals.

• Mahisha Dellinger ( Below Deck Med Season 9, Episode 11)

  

  Aesha Scott couldn’t have been happier that television host Mahisha Dellinger booked a short charter. Upon entering the mega-yacht, Dellinger forced the interior team to move the sky deck’s couches, which she called an “eye sore,” so she and her friends could take photos. Nothing was quite right for Dellinger, who later complained that the caviar tasted like a “washcloth.” Her friend Neysla Paltsev even attempted to jump on the bandwagon by criticizing the utensils they were provided at dinner. When Scott proved her wrong, Paltsev fired back that their “caviar service sucked.”

• Athena Lucene ( Below Deck Med Season 6, Episode 7)

  

  Athena Lucene certainly wasn’t an awful guest, but she sure did keep the crew on their toes. Hosting an entrepreneur retreat for her clients, Lucene expected immediate gratification at all times. When chef Matthew Shea held off a few extra minutes on dinner to wait for all the guests to sit down at the table, an impatient Lucene took it upon herself to go into the galley and ask what the holdup was. She then forced chief stew Katie Flood to move her seat to the head of the table as she felt “awkward” sitting on the side, before requesting that the already-behind chef whip a last-minute salad for everyone. Lucene was also “disappointed” with the cakes Shea decorated, though, to be fair, they were underwhelming.

• Brandy ( Below Deck Season 7, Episodes 3 & 4)

  

  The Below Deck crew has dealt with tons of drunk charter guests. But Brandy, who appeared in the show’s seventh season, might have been the most terrifying. Having clearly gone a tad overboard on the champagne (no pun intended), a passed-out Brandy was swiftly hauled away from the beach picnic to see a medic on the yacht. However, her friends seemed unfazed as they didn’t let her episode ruin their time on the island.

  Each Below Deck series is currently streaming on Peacock .

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