Over-the-top vacations have always been a signature set piece of Keeping Up With the Kardashians. This season, subsets of the family have been to Vail and Iceland. Now, the destination is Cuba, which provides a wealth of opportunities for awkward cluelessness. Before anyone escapes to more tropical climes, Khloé catches us up on what is going on with Lamar, or, more specifically, Lamar’s schedule. She calls to schedule an eye doctor appointment for him but explains to the office that he was in a coma, so he’s got a list of medications longer than the form would allow. She tells Malika that he’s had a manicure, a massage, and a dermatologist is going to make a house call. She is apparently working as concierge now for her ex-husband. “I’ve put my life on hold to help get him on track,” she says. He’s also got a lot of “internal” work to do on himself, and she can’t schedule that for him. But more on that later. Now it’s time to plan a trip. Kendall is scheduled to walk in the Chanel show in Havana. Khloé thinks this is the perfect time for everyone to clear their schedules and fly south. Malika is in. Seriously, though, when is Malika ever not in? “It’s on my bucket list, so I’m totally happy to go,” she tells Khloé. At Kris’ house, Kim and Khloé tell their mom that the whole gang has decided to go on the trip. Kris is not down with this vacation. She reminds her daughters that there is no WiFi in Cuba. Kris can’t be out of communication for that long. She has work to do. Kim and Khloé roll their eyes at that, and it's full steam ahead for the trip. “You don’t communicate anyway,” Khloé says to her mom. “I hear the sangria is to die for,” Kim says.
Kourtney and her kids and Khloé and Malika are the only ones in the jet to leave from L.A. for Havana. Scott didn’t get his act together in time to get his visa sorted. Kim and Kanye are in New York, so they’re meeting them there. It also turns out that Kendall, the entire reason for the trip in the first place, is no longer walking in the Chanel show, so she’s a no-show, too. Khloé is nervous about leaving Lamar and being completely incommunicado. Kourtney’s only concern is having enough DEET to ward off Zika mosquitos and no place for car seats in the classic cars. She’s excited for them all to make some memories, a recurring Kardashian travel theme. Khloé and Malika go for a drive in a 1957 Chevrolet convertible. It is hard not to feel uncomfortable watching the sightseeing in Cuba. What is probably intended as friendly curiosity mostly comes off as clueless gawking. There are awkward comments about goats and how nice the people are in Cuba. “Yes, that’s what I like is real life,” Khloé says to their driver Armando. “Tone-deaf” is a word that comes to mind.
Kim and Kanye and their children arrive. Kim is excited to be with Kanye in a place that he has never been before. “Isn’t this like a dream come true to come to Cuba with your husband and your two kids?” Kanye asks his wife. Kim is, indeed, thrilled. “It hasn’t changed for decades, and it’s so amazing,” she says. Again, a little tone-deaf. As usual, Kourtney demonstrates that she is most adaptable, despite some of her quirks about food and chemicals. When she says she likes to walk the streets and talk to people, viewers can almost believe her. At dinner, Khloé confides in Malika that she has heard that Lamar is asking for cash while they are away. Malika tells her that Khloé has done everything she can do, but she can’t control it. Khloé feels that Lamar was just waiting for them to leave. That’s what he used to do before when she would leave town. She is convinced his destructive patterns are starting again. Kris isn’t enjoying the “peace and quiet” in L.A. like she told Kim and Khloé she would. She misses the texts the most and is sitting on pins and needles to hear news. To break the monotony, she goes into cleanup mode, sending Kardashian beauty products to the “underprivileged women downtown for Mother’s Day.” No comment. In Havana, they visit an artists' collective that is filled with genuinely amazing art and artists. This is the spot where having the bright spotlight that comes with a visit from Kim and Kanye might do some good on this vacation. That and it is hard not to laugh when they ask North what she is going to be when she grows up. “Are you going to be an artist?” Kanye says. Nope. “A bunny,” North declares. It wouldn’t be a trip to Cuba without some rum and cigars, so they visit a rum distillery. Kim wants to soak it all up. Pun intended. “Even though I’m not that big of a drinker, I’m enjoying all the memories,” Kim says. Memories. Always with the memories. Like a video record of your life for 12 seasons isn’t enough? Kanye doesn’t express his need to make memories. He likes the distillery for more basic reasons. “I’m actually super into this because I like fire, and I like alcohol.” In California, Kris still can’t fill the void left behind by her eldest daughters. She pops over to Kylie’s house. Kylie is in the middle of a photo shoot for a new Lip Kit (this one appears to be blue) and says her standard line: “It’s so exciting to be part of something I have always wanted since I was little.” It is never clear exactly who she is trying to convince. Kris is looking for attention but isn’t getting it from the youngest Jenner. “I’m just not used to not hearing from anybody,” Kris says, lamenting the radio silence. Lamar comes up again in Cuba. Kim explains the situation to Kanye. Khloé tells them that he quit his physical therapy early. She has asked him to go to counseling because she doesn’t know how to help him with that. “It’s really hard to see Khloé so stressed,” Kim says. She wishes her sister wouldn’t put all of that weight on her shoulders. Old patterns are repeating themselves. After the photo shoot, Kylie heads to her mom’s house for a cooking lesson to make Kris’ famous pasta primavera. “I feel like my mom complains a lot that she has too many children, but I feel like she needs us,” she says. Kris appreciates the gesture. She thinks Kylie is the only one who really listens to her. With the oldest three out of touch and Kendall traveling, that certainly seems true. Corey looks the most relieved that Kylie showed up to keep Kris company. In the last moment from Cuba before the second half of the two-part trip, Kourtney and Kim visit Ernest Hemingway’s House and Museum. Kim discovers that she and the author of The Old Man and the Sea have something in common. Apparently, Hemingway would weigh himself every morning and write it on the bathroom wall. “That’s like me!” Kim says, inexplicably. Best not to drill down too deep on that one.