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Need itinerary advice regarding Ibiza and Gibraltar

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My husband and I will be traveling by boat (a business trip- set in stone) from Gibraltar to Ibiza in early October. We were thinking of tacking on a few days to one of these locations or something else nearby. From reading posts on the forum, I'm guessing that most would recommend Ibiza over Gibraltar, especially since we should have time to see the rock, monkeys and tunnels anyway. However, by the time we reach Ibiza, the clubs will be closed and the weather may be too cool for beach time. So, I'm thinking about spending two or three nights somewhere near Gibraltar at the beginning, then driving back and walking over the border to embark on the boat trip. Any suggestions? We're in our 50's and enjoy the dining, history, culture and active aspects of travel.

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