Longtime best friends, Tara and Jessica, want to rule their 30th High School Reunion, but their plans go sideways when everyone is forced to tell the truth. Andi wants to know if her cat BoBo loves her as much as she loves him. Roarke juggles a secret romance, as Ruby and Gina spend more time together.

In the wake of her mother's passing, Helene visits the Island in search of her biological father. She thinks he might just be one of the guys who's come to celebrate a Bachelor Party. Roarke and Javier grow closer, while Ruby gives herself a spiritual cleanse with a bonfire and a night swim, where she encounters an old friend.

Empty nesters Dolly and Dutch seek clarity on how to spend their next chapter. Meanwhile, Helene helps Ruby tap into her newfound youth. Javier opens up to Roarke as he wrestles with his new role.

Three best friends of fifty-plus years set out to track down the missing fourth member of their squad... in 1980s Miami! Meanwhile, Roarke confides in Segundo about letting people in, and Ruby's cabin fever is an itch that needs to be scratched.

After an urn comes off the plane, three siblings must work through their past resentments in order to spread their mom's ashes and fulfill her last fantasy. As the kids wrestle with their past, Roarke remembers their mom, her very first guest as the host of Fantasy Island. Meanwhile, Ruby is surprised to discover how little she knows about Isla.

Oliver's fantasy is to surprise his boyfriend Emilio with the perfect proposal, but when Emilio says no, Oliver finds himself reliving that day over and over again. Meanwhile, Roarke, also caught in the time loop, must confront her fears about her relationship with Javier.

Amber's fantasy is to have her actual life be as perfect as her Instagram life. But when Amber's family transforms into the perfect Insta-versions of themselves, she soon realizes something about all this perfection is very wrong. Meanwhile, Roarke presents another guest, Isaiah, with an envelope that reveals the date of his passing.

A country music star with writer's block, Shay, fantasizes about being anonymous so she can focus on finishing her next album. Her beleaguered assistant, Beau, is surprised when Roarke offers him a fantasy too. When their fantasies begin, Shay and Beau realize they've traded places: Shay is a complete unknown and Beau is the star. Javier learns something new about Helene's life before her mother's passing.

Gwen's fantasy is to go back in time and be the Princess she longs to be-pampered, rich, and cared-for. At first, the fantasy is everything she dreamed of-the gowns, the pageantry, everyone bowing to her. But Gwen soon finds out the King is preparing to marry her off to a cruel, ambitious Prince. With the marriage looming, Gwen has no choice but to flee. She befriends a Soldier and together they hatch a dangerous escape plan. Ruby isn't feeling like herself and Roarke suspects it has something to do with Isla.

A middle-aged couple and a younger couple arrive separately with their own unique fantasies. All is going well until the couples discover they're sharing the island; turns out they're feuding neighbors. The Island forces them into a magical, winner-takes-all competition that reveals unexpected alliances and unravels complicated relationships. Meanwhile, Javier and Roarke finally have a conversation about their relationship.

Jilted bride Laura arrives on the island still in her wedding dress, having just been stood up at the altar. She's never felt worse in her entire life, and her fantasy is to just feel better. The Island surprises her with her childhood imaginary friend, Peaches, in real human form and helps Laura rediscover that her inner child is exactly who she needs to move on from her heartache. Isla tells Ruby about the complicated past between her people and the Roarkes.

The Island gives single mom Courtney the ability to read minds in order to impress her charismatic boss, Julia. But when Courtney becomes overwhelmed with her new power, she risks everything she has worked so hard for. Meanwhile, Roarke is worried that Ruby is becoming more and more distant and enlists Javier to help.

Sue, Jenna and Brooklyn are the first, second and third wives of Gavin, a charming doctor who's made a fortune selling all-natural vitamins - and broken all of their hearts along the way. Now, they all share the same fantasy: they want Gavin to understand - to feel for himself - the pain he's caused them all. Meanwhile, Roarke brings Ruby's youngest daughter, MJ, to the Island to help Ruby remember who she is. And hopefully keep her from disappearing into the ocean forever with Isla... as a mermaid.