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Road Trip from RI to Key West Florida

Hi everyone, we are taking a road trip from RI to Key West Florida. We have 11 days for the whole trip. Here is the current plan:

Day 1 drive from RI to Chesapeak VA - staying overnight at a friends
Day 2 - spending the day at Kitty Hawk and the Outerbanks - camping overnight
Day 3 - drive to Gainsville Florida (we will spend 3 nights here - vising friends)
Day 6 - drive South to North Port Florida - staying overnight with family
Day 7 - drive South to Key West Florida (spending 2 nights)
Day 9 - drive to Fort Lauderdale - to visit family - we will not be spending the night here - the rest of the trip is currently open
Day 12 - I would like to wake up in my own bed in RI

What I need to know is - what are the MUST sees. We have been told that we must see the South of the Border Rest stop and visit Pedro's Hat. I love kitchy stuff like this - We will also be taking a picture at the southern most point in Key West. What else can you suggest? More than likely we will mostly be traving on 95.

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