Florida Keys
#2
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I just checked mapquest.com and it says Ft.Myers to Miami is a couple of hours...considering they usually exaggerate travel time, it would still make a trip down to Key West VERY long. From Miami to Key West is 4 hours in good conditions. The upper keys are known primarily for being laid back and for water sports and snorkeling/diving. Key West is known for great restaurants, great accommodations, and lots of tourist activities. As much as I love Key West, I don't think you'll have enough time to drive all the way down.
#3
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Our daughter lives in Key West and has driven up to see us in Ft. Myers and it usually takes her 5 to 6 hours. Weekends can take longer in the Keys due to traffic. Depends on what you want to do on whether you want to drive down to Key West. More to do and see in Key West than Key Largo.
#4
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We drove very happily from Sanibel to Key Largo in a day with several sightseeing stops but I wouldn't have wanted to go on to Key West that day. On the other hand I think there's far more to see and do on Key West and the lower Keys. How about an overnight stop at Key Largo then on to Key West for a couple of days?