The reality TV franchise Below Deck is set on a luxury yacht, with a crew expected to provide demanding and obscenely wealthy guests with everything they ask for during their short stints at sea. Viewers also watch the crew members cut loose and relax between sailings. The best Below Deck seasons include a balance of smooth sailing and drama. Nowadays, the series has multiple spinoffs, which follow the same theme, with just as many fun (but sometimes troubling) guests.
After dealing with guests, the crew must find time to relax before the next charter. From drunken, boorish behavior to guests who make impossible requests (and some who don’t know how to take no for an answer), the Below Deck franchise shows that working on a luxury yacht is not exactly a dream job. While guests' antics don't come close to the most shocking Below Deck moments, they can definitely cause a stir.
10 Delores
Below Deck (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 very tired when dinner ended. However, instead of calling it a night, Delores kept the party going by attempting a late-night swim. Delores’ friends (and the crew) warned her that she wasn't allowed to swim in the ocean at night, as it was a safety hazard.
Captain Lee Rosbach stepped in and warned her that he'd send her home if she jumped in the water. To spite them all, Delores ignored everyone, and dove into the ocean. The following day, Captain Lee sent Delores packing. However, she proceeded to jump off the mini boat to shore. Dramatic times like this make Below Deck one of the best reality shows.
9 Brandy
Below Deck (Season 7, Episode 3)
A season 7 episode nearly ended in disaster after one of the guests had far too much to drink on Below Deck. Charter guest Brandy 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 because of how dangerous the situation could have been. There are plenty of fake things about Below Deck, but this action was not one of them. Brandy was a demanding charter guest because of her negligence and stress-inducing behavior.
8 Nichelle Gainey And Areca Whatmore
Below Deck Mediterranean (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 instead of plates was just the start of their confrontations with the crew. They even escalated their complaints to Captain Sandy, who had more important things to worry about than whether someone’s wine glass was empty or the dish their pasta was sold in.
7 Steve Bradley
Below Deck (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 team, who found it challenging to deal with his rowdy behavior. He was one of the series' most flirty guests, which always resulted in a problematic charter. While he wasn’t the worst Below Deck guest, he was undoubtedly one of the most demanding and unpredictable clients Captain Lee and his team had to deal with.
6 The Florida State Alumni Crew
Below Deck (Season 7, Episode 7)
In season 7, friends who met 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 get her out of an unpleasant situation she should have never been in. The guest’s behavior crossed a line, making him one of the worst.
5 Charley Walters
Below Deck (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 had the chef running around in circles trying to meet all his exacting demands. Being one of the best deckhands on this charter was challenging because of how demanding Charles and his friends were. Walters later claimed on social media that producers told him to be over the top. Still, a fine line exists between entertaining and being so complex that professionals have difficulty doing their jobs.
4 Simon Tusha
Below Deck (Season 1, Episode 4)
Simon Tusha, the owner of the company which provided the luxury yachts for the Below Deck series, was featured as a guest in season 1, and his behavior went down like a lead balloon with the crew. He made inappropriate comments to female crew members and was rude to Kate.
Worst of all, chief stewardess Adrienne Gang refused to support her crew, insisting they had to get used to Simon’s sense of humor. According to The Pittsburgh Post, after the episode aired, Tusha was sentenced to 21 months in jail for his part in a bribery case. His entire persona on deck matched what was said about him in court, making him one of the show’s more controversial.
3 Charles Yim
Below Deck (Season 6, Episode 5)
According to Cheat Sheet, below Deck guest Charles Yim claimed 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 My Seanna, and perhaps the most shocking moment was when the crew found a used condom in the living area. The entrepreneur said that much 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. These guests were not the best because of how awkward the charter was.
2 Krystal Murphy
Below Deck (Season 6, Episode 15)
Cyndi Lauper sang, "Girls Just Wanna Have Fun," but investment banker Krystal Murphy and her friends said girls want copious amounts of alcohol and fistfights with each other. After over-indulging in co*cktails and wine, the primary charter guest fell asleep at the dinner table before punching one of her friends in the face. She made outrageous demands throughout the trip, leading one of Below Deck's best chief stews, Kate, to label her a “spoiled brat.” She will undoubtedly go down in history as one of the most obnoxious Below Deck guests ever.
1 Timothy Sykes
Below Deck (Season 2, Episode 10)
According to Cheat Sheet, when Captain Lee was asked about the worst Below Desk guest, he didn’t hesitate with his answer: Timothy Sykes, the entrepreneur with a much younger girlfriend who spent the whole trip complaining that there was no Wi-Fi and that the kitchen crew was ignoring all their particular food requests.
To make things worse, Sykes handed over a $17,000 tip at the end of the trip but then asked Captain Lee to give him back $5,000 because his girlfriend didn’t like the food. In the service industry, there's nothing worse than having to give money back to a guest. For this reason, Sykes takes the cake of the worst guest in Below Deck history.
Source: The Pittsburgh Post, Cheat Sheet, Cheat Sheet
