I had a good time hunting Smathers beach at Key West last November. Found a cool statue. Look by the exits, people drop change on the way to feed the parking meters. Park across the street, it's free.
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Smathers Beach! Thats the one, and it sounds like it hasnt changed, either. As I recall, there was nothing but vacant rubble lots and mangroves across the road from the beach, all one end of the "International Airport".
Youll have to do some scoping ahead of time to learn where the people congregate. This is NOT the main tourist season, so you will be coming behind any other pirates. But there should be some goodies to find.
Also visit Turtle Kralls, on the other side of the island. Its a cool bar that used to be a turtle pen, where sea turtles were corraled ("kraal" is a dutch word for corral) prior to slaughter for the restaurant trade - yep you used to be able to get sea turtle to eat.
Now they sell beer from all over the world - and if you drink enough of them according to a plan, you get a free t-shirt. Earning one of these shirts is a challenge, as you had to drink 31 different beers back in my day to get one. These shirts are a badge of honor among the locals - I had two of them at one time.