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How many nights to spend in Key West?

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Please advise as to how many nights (or full days) to spend in Key West. I've never been but always wanted to visit, so I would like to leisurely explore and enjoy it and the surrounding area. Maybe Key Largo as well?

One tentative plan is to fly into Miami, pick up a rental car, and drive to Key West. Maybe from Thursday or Monday or Tuesday? Will that give us enough time, factoring in the r/t drive to/from the Miami airport? The problem is that one friend can go at most from Thursday to Monday, but another friend is willing to go from even Wednesday to Tuesday.

Thanks in advance for your help!

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