Below Deck: The Worst Guests On The Yachts, Ranked

The reality TV show Below Deck is set on a luxury yacht, with a crew who are expected to provide their demanding and obscenely wealthy guests with anything and everything they demand. Viewers also get to see behind the scenes, or below deck in nautical terms, as the crew members cut loose and relax between sailings.

And they do need to find some time to unwind, given how terribly some of the guests behave. From drunken, boorish behavior to clients who make impossible requests – and some who don’t know how to take no for an answer – Below Deck shows that working on a luxury yacht is not the dream job that it seems at first glance. These are some of Below Deck’s worst guests.

Updated on July 29th, 2021, by Lynn Gibbs: Watching the crazy ups and downs of the yachting industry on Below Deck was such a hit with fans that it spiraled into two spin-offs: Below Deck Mediterranean and Below Deck Sailing Yacht. And while fans tune in every week to stay updated on the highs and the lows of the crew, they also can’t wait for Below Deck’s guests. While most guests are genuinely humble and grateful for the tremendous service and views, there are also terrible guests. Some of the worst Below Deck guests are those that demand the world and give little respect to the crew.

13 Johnny Damon & His Wife (Season 4, Episode 10)

Johnny Damon isn’t a Bravolebrity but he was controversial. Damon was a legend in professional baseball and is now relaxing with the millions that he’s made. He arrived with his wife and some friends in season 4 for a little getaway, but it quickly became ugly the more alcohol they drank.

When the boat was docked, Johnny’s wife got into a screaming match with a man from the neighboring charter. It prompted the crew to get involved and kick the man off their charter. The couple came back in season 5 with even more drunken mishaps and mistakes, but season 4 was the worst.

12 Gumball Girl (Season 3, Episode 7)

There have been six seasons of Below Deck Med. filmed on different superyachts in various parts of the Mediterranean, but the one thing all the shows have in common is that the crew are the stars. Often, viewers don’t even find out the names of all the guests, as was the case with the anonymous female passenger who made the team jump through hoops when she asked for gumballs.

When the crew could only produce white gumballs – which she hated – she threatened to have them helicopter some other flavors aboard just to satisfy her craving. Fans didn’t know how Captain Sandy was going to react to it but she left it in the hands of her crew.

11 Adrienne Gang (Season 2, Episode 6)

Adrienne Gang is best known as the chief stewardess on the first series of Below Deck, but she was replaced by Kate Chastain for the second season. Being a chief stewardess is a tough role, and Adrienne didn’t always get on with the rest of the team, which is why some of her former crewmates were horrified when she turned up as a guest.

Adrienne made the most of her guest appearance, stirring things up between Kate and Amy, and spilling all the Below Deck gossip to her fellow guests. She wasn’t the best stewardess, but she did make things juicy in season 2.

10 Midnight Swimming With Delores (Season 8, Episode 11)

In season 8, a guest named Delores had far too much to drink after a day on the water and was overly tired by the time dinner ended. However, instead of calling it a night, Delores kept the party going by attempting a late-night swim.

Her friends and the crew warned Delores that she was not allowed to go swimming in the ocean at night as it’s a safety hazard. Even Captain Lee stepped in and warned her that if she jumped in the water, he was sending her home. Delores ignored everyone and jumped into the ocean to spite them all. The following day, Captain Lee sent Delores packing where she proceeded to jump off the mini boat to shore. It’s dramatic times like this that make Below Deck one of the best reality shows on Bravo.

9 Brandy (Season 7, Episode 3)

A season 7 episode nearly ended in disaster after one of the guests had far too much to drink. Brandy (viewers never learned her surname) seemed to have already had a few drinks when she boarded the yacht, and when the group later went ashore for a picnic the crew became so concerned about her wellbeing that they took her back to the ship for medical treatment.

It was a moment that separated Below Deck from other reality TV shows and she was easily one of the show’s worst guests.

8 Nichelle Gainey And Areca Whatmore (Season 3, Episode 2)

Friends Nichelle Gainey and Areca Whatmore made quite an impression on the crew when they boarded the Talisman Maiton on Below Deck Mediterranean. Perhaps the two women were not used to the finer things in life, but their outraged reaction to being served pasta in bowls (as is normal in Italy) was just the start of their confrontations with the crew.

They even escalated their complaints to Captain Sandy, who has more important things to worry about than whether someone’s wine glass is empty. If there was one thing Below Deck taught fans about the yachting world it’s that they’re only as happy as their least happy guest.

7 Steve Bradley (Season 3, Episode 1)

Steve Bradley was one of a handful of guests who made two appearances on Below Deck, first in season 3 when he demanded that the crew throw him and his friends a foam party, and again in season 6 when he continued to make outrageous demands of the crew, who found it difficult to deal with his rowdy behavior. He was definitely one of the most flirty guests in the series.

While he wasn’t the most problematic Below Deck guest, he was certainly one of the most demanding and unpredictable clients Captain Lee and his team had to deal with.

6 The Florida State Alumni Crew (Season 7, Episode 7)

In the seventh season, a group of friends that met each other at Florida State in their younger years hopped on the yacht for pirate-themed nights and to relive their college days. Unfortunately, the charter guest, Michael, was inappropriate from the start.

He began flirting with stewardess Simone and continued making advances towards her, regardless of showing how uncomfortable she was. Kate Chastain eventually stepped in and put Simone below deck to essentially get her out of a disgusting situation.

5 Charley Walters (Season 8, Episode 14)

Demanding guest Charley Walters has made three appearances on the show, each more outrageous than the last. He has a penchant for making the male crew members dress up in tiny Speedos while serving dinner and drinks, and has the chef running around in circles trying to meet all his exacting demands. It was a hard time to be a good deckhand on this charter.

Walters later claimed on social media that producers told him to be over-the-top, but there is a fine line between being entertaining and being so difficult that you just come off as being boorish and vulgar.

4 Simon Tusha (Season 1, Episode 4)

Simon Tusha, the owner of the company which provided the luxury yachts for the Below Deck series, also featured as a guest in season 1, and his behavior went down like a lead balloon with viewers. He made a series of very inappropriate comments to female crewmembers and was particularly rude to Kate.

Worst of all, chief steward Adrienne refused to support her crew, insisting that they just had to get used to Simon’s sense of humor. Tusha was later sentenced to 21 months in jail for his part in a bribery case. His entire persona and life after the Below Deck practically became a meme in itself.

3 Charles Yim (Season 6, Episode 5)

Below Deck guest, Charles Yim also claimed that the show made his stay on the yacht look worse than it was. Yim and his guests certainly made the most of their time on the MV Seanna, and perhaps the most shocking moment was when the crew found a used condom in the living area.

The entrepreneur said that a lot of what was shown on the episode simply didn’t happen and that the crew even made fun of him and his guests because they wanted to spend some of their time working.

2 Krystal Murphy (Season 6, Episode 15)

Cyndi Lauper sang that “girls just wanna have fun,” but according to investment banker Krystal Murphy and her friends, girls just wanna have copious amounts of alcohol and fistfights with each other.

After over-indulging on cocktails and wine, Krystal fell asleep at the dinner table before punching one of her friends in the face. She continued to make outrageous demands throughout the sailing, leading crew member Kate to label her a “spoiled brat.” She will certainly go down in history as one of the most obnoxious Below Deck guests of all time.

1 Timothy Sykes (Season 2, Episode 10)

When Captain Lee was asked about the worst Below Desk guest, he didn’t hesitate with his answer; Timothy Sykes, the entrepreneur with the much-younger girlfriend who spent the whole trip complaining that there was no wi-fi and that the kitchen crew was ignoring all their very specific food requests.

To make things worse, at the end of the trip Sykes handed over a $17,000 tip (standard for these kinds of voyages) but then proceeded to ask Captain Lee to give him back $5,000 because his girlfriend hadn’t liked the food. He was definitely one of the worst guests on Below Deck.