The episode begins and Annie on her part attempts to extract info from Simon about an upcoming business trip on. He in turn suggests that Annie come to Cuba with him. Later, Annie arrives at Lena's home and says she wants to go. Lena on her part makes it clear to her the Agency wouldn’t be able to rescue her if she got in trouble. Lena therefore can approve the whole thing, but she on her part has no authority to stop Annie. She in the end tells Annie that she shall arrange a new passport for Annie, so Annie can’t be tracked by the Agency. At Langley in the meanwhile, Auggie inquires with Annie regarding the trip she is embarking on, Annie in turn lies that she is going for a vacation.
He though seemingly doesn’t buy into her vacation story. Lena later gets Annie her fake passport. Annie is then shown getting past customs in Mexico without a hassle, she then proceeds to Cuba. Later at the airport, Simon gives Annie a ride on his motorcycle. Once home, Simon takes Annie’s passport from her, telling her that he is taking it for safekeeping. Annie albeit reluctantly, hands the passport over to him. Meanwhile at Langley, Lena asks Joan to relax her habit of micromanaging a bit. Arthur is asks Auggie that he be allowed back into Jai’s investigation. Auggie tells him that he wants to have a talk with Harvey Wilcox. Arthur on his part feels is a waste of time. In Cuba, Simon and Annie have a heart to heart and Simon tells her how he wishes he could look at the world the same way Annie does.
Joan in the meanwhile tells Arthur he has her support in the decision of him opting for the job of the Chinese Ambassador; she even wants to host a dinner for the same. Simon and Annie are meanwhile having dinner. Simon recounts to Annie the experiences of his childhood. A man is shown keeping a watch on both of them. Simon asks Annie about her experiences. He then proceeds to leave telling Annie he has a meeting and shall meet up with her at the house, in an hour’s time. Annie then follows Simon, as she feels something is amiss. She later follows him on a bike, after buying one from a person the street. It is then shown that Simon is meeting the man from the restaurant, who was keeping a watch on them.
Annie in the meanwhile is doing her best to keep a watch on them, despite facing a few impediments on the way. She later gives Lena a call, and describes to her the place she is at. Lena on her part explains to Annie that she is at KGB’s listening station, turns out its old and the largest, and as it turns out its also operational. The station can be turned in a cellular jamming station, which would be able to interrupt FAA and every other kind of signal. This can be done with the help of the hardware stolen by Simon. Annie then tells Lena how her passport has been taken away from her, by Simon. Annie then describes the man Simon is talking with, to Lena. Lena based on the description, concludes that the man is Hector Serrano who as it turns out is FSB’s main man in Cuba.
Serrano was earlier a hitman for FSB. Lena warns Annie about Serrano and asks her to be wary of him, and basically asks her to stay away from him. Later Annie goes back home, where Simon introduces Annie to his friends Hector Serrano and her girlfriend Blanca. He tells her that, they are there to have dinner. Annie and Blanca have a chat and she tells Annie how Simon and Hector have some business together, due to which they see Simon quite frequently. She also hints that their business together is nearly done. Joan and Arthur in the meanwhile organize things for their guests who are slated to arrive for dinner. At Petersburg Prison, Virginia pays Henry Wilcox a visit. He begins by hurling accusations at Henry saying, Harry is withholding information.
Henry is visibly outraged by the accusations and therefore ends the interview and leaves in a huff. Annie and Hector are shown having an argument that is political in nature. Blanca in the end apologizes to Annie on Hector’s behalf. She later interjects that she has never seen Simon so happy. Later, the couples are shown dancing. Hector during the dance seems to have an eye for Annie and even tries to cut in and have a dance with her. Simon though resists his attempts, Annie though is fine with Hector wanting have a dance with her. He tells Annie he has never met a middle rung museum employee who had an opinion about international politics.
He then takes her by complete surprise when he questions her about her sister Danielle and what she does for a living. Annie is visibly taken aback, as she never brought up the mention of Danielle, during their conversation. She consequently ends the dancing. Later, Hector in Russian tells Simon that there is more to Annie than meets the eye and that she might pose a serious problem to their business deal. Simon on his part makes it clear to Hector that he has the whole thing under control; Hector though isn’t convinced by Simon’s assurance and tells him that he shall have to do something, if Simon doesn’t deal with the issue. Later Annie asks Simon if them coming on the trip was too much of a good thing, and if the decision was bit too impulsive.
Both in the end conclude that it would be better for them to go back home, the next day. The two then spend the night together, in bed. Meanwhile at the dinner party hosted by Arthur and Joan, a guest mentions how Arthur’s timing of the nomination couldn’t have been better. He basically insinuates that Arthur can take the job and leave the mess for the next guy to clean up. Arthur as it turns out is visibly offended by this insinuation and reprimands his guest for it. In Cuba, Simon reveals to Annie that he has planned a sightseeing trip with Hector before they fly out on the noon of the very same day. Annie is visibly concerned by this plan that has materialized out of the blue, but plays along. The two then leave in a car with Hector. Later, Hector takes them to a cigar-rolling factory.
Once inside, Annie flicks a tobacco cutter on the sly, and ensures that it escapes Hector’s notice. Annie is then taken to a storage room by Simon, who plays a trick on her by asking her to go into the room. She is then locked inside the room by Simon. The storage room door has a peephole, through which Annie sees Simon slitting Hector’s throat with a knife. He then quickly releases her and urgently tells her that they have to leave. They hurry back to the car and Simon then takes Annie to the airport. He then assures her that he will see her soon. Then after giving her passport back, he kisses her goodbye. At the Petersburg prison in the meanwhile, Henry is once again summoned by Auggie.
Auggie then tells him that the mystery of Jai’s murder shall remain unsolved if he doesn’t help. Henry in the end reveals to Auggie the location of Jai’s safehouse. Arthur in the meanwhile makes it clear to Joan than he doesn’t want to leave the investigation of Jai’s death halfway. He has thus decided to give up on the nomination. Annie is back, and informs Lena about all that transpired in Cuba. Lena is convinced after hearing everything that, Simon is in love with Annie and feels that this very fact can prove quite advantageous for them. Annie on her part seems to agree, but apparently isn’t as excited. The episode ends.