To celebrate their milestone 300th episode, Bobby and Jim return to recap their recent separate vacations to two very different places named Naples. Bobby shares wild, chaotic stories from his trip to Italy—including navigating bullet trains, dealing with aggressive tour guides, visiting a gay nudist beach in Palermo, and surviving a sudden police raid at an underwear club in Rome. Meanwhile, Jim contrasts that with his ultra-conservative, deeply relaxing family trip to Naples, Florida, where a restaurant waiter hilariously mistakes him and his husband for brothers. The duo wraps up the milestone episode by ranting about international airport baggage customs, discussing their partners' intense road rage habits, and exposing the "fake facades" of dating app profile pictures.

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