The Kyles are leaving for their family vacation on Hawaii, but instead of taking only one flight straight to the island, Michael thought it would be a good idea to make a quick tour around the country, so they make stops at New York, Chicago, Denver and other cities before they get to Hawaii (two days later). When they finally get there, Michael's luggage gets lost and they're forced to take a master suite because their reservation expired. While Michael wants to make it a romantic and resting trip, Jay wants to get to know place, and drags the entire family on a historical tour – except for Michael, who chose to sleep in. The kids are sick of the tour and go back to the hotel. Jr. tries to meet women and buys a book on how to talk to women subliminally, while Michael keeps scaring away any guy who lays his eyes on Claire.
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