Most famous people to charter on Below Deck

Below Deck, the hit reality TV franchise on Bravo, has hosted a variety of charter guests over the years—some of whom are celebrities or well-known public figures. While most guests are wealthy but relatively unknown, a few high-profile names stand out. Here are some of the most famous people to charter a boat on Below Deck (including its spinoffs like Below Deck Mediterranean and Below Deck Sailing Yacht):

🔹 1. Johnny Damon – MLB Star

  • Appeared On: Below Deck Mediterranean and Below Deck

  • Details: The former MLB player and two-time World Series champion (Red Sox, Yankees) chartered multiple times with his family. His wild parties and drinking made his charters especially memorable.

🔹 2. Roy Orbison Jr. – Musician and Son of Roy Orbison

  • Appeared On: Below Deck Mediterranean

  • Details: The son of the legendary rock singer and a personality in his own right, Roy Jr. was lively and had a good rapport with the crew.

🔹 3. Justin Thornton & Jonathan Sadowski

  • Appeared On: Below Deck Mediterranean

  • Details: Actor Jonathan Sadowski (Young & Hungry, Chernobyl Diaries) and fashion designer Justin Thornton chartered together. Though not A-list, their episode attracted attention.

🔹 4. Delores Flora – Infamous Party Guest

  • Appeared On: Below Deck Season 8

  • Details: Not a celebrity, but became internet famous after drunkenly jumping overboard at night—a major safety violation. She went viral and was discussed across entertainment news.

🔹 5. Jemele Hill & Cari Champion – Sports Journalists

  • Appeared On: Below Deck Season 9

  • Details: The former ESPN personalities brought a fun, outspoken energy. Their appearance was praised for showing strong women having a good time without drama.

Honorable Mentions

  • Charley Walters – A recurring guest known for dramatic and lavish charters. Formerly a baseball player and now a publicist/event planner.

  • Krystal Murphy – Not a celebrity before the show, but became infamous due to erratic, entitled behavior.

  • Barrie Drewitt-Barlow – British millionaire and media personality known for his unconventional family and reality show presence.