The pressure mounts as the crucial hometown dates loom, but before returning stateside, Sean takes the remaining six bachelorettes to romantic St. Croix. AshLee not only risks revealing a secret about her past, but also decides to go on the attack when it comes to Tierra. Tierra, feeling anxious about her relationship with Sean and how the drama with the other women will influence his decision, desperately discloses something that will shock him. Lesley’s individual date has her re-thinking her strategy. Sean, confused over whom he should send home, invites his sister to St. Croix to help him sort through his feelings. A huge drama erupts at the hotel and Sean knows what he must do, dropping two bombshells and leaving the four women who will take him home to meet his families.
Sean scoops up AshLee for a romantic ride on a catamaran to a private island. They seem to be falling more and more in love. Sean feels so comfortable with AshLee that he asks her about the drama between the other women, and she wastes no time in trashing Tierra. However that night AshLee decides to share something about her past that might jeopardize her chance at getting a hometown date.
Tierra and Sean meet on the streets of St. Croix and explore the town. Sean takes this opportunity to ask his date about the rumors he has heard about her behavior, but she is quite unapologetic. But now Tierra is apprehensive about her chances of getting a hometown date, and takes a calculated risk divulging a stunning bit of information. But will it be enough?
Sean surprises three women, waking them up at 4:00 a.m. so they can go see the sunrise at the easternmost point of the U.S. During the day, the group travels across the island in time to see the sunset at the western edge of St. Croix. Each woman gets quality time with Sean. One bachelorette opens up about a dark family secret. Another woman breaks down talking about her family. But one makes a clear impression, gets the rose and captures a hometown date.
On the final day on the island, Sean hopes to push his relationship with Lesley along, feeling that it is behind the others. After exploring the ruins of the Mt. Washington sugar plantation, he asks her if there is anything else she would like to say. She worries about not sharing her true feelings with Sean and hopes that it won’t keep her from taking him home to meet her family.
Sean’s sister, Shay, journeys to St. Croix to help her brother sort out his feelings, and cautions him about what kind of woman would not be good for him. Meanwhile, two women are going at each other, one accusing the other of sabotaging her time with Sean. The accusation escalates into the biggest meltdown in “Bachelor” history. Sean, however, doesn’t have any idea what happened at the hotel, but soon sends a shockwave through the group. The women are panicked about what lies ahead at the rose ceremony and break into tears with self-doubt as they wonder what the Bachelor is really looking for in a soul mate. But Sean manages to narrow the field to the four lucky bachelorettes who will take him to their hometowns to meet their families.