"sitting on the dock of a bay..."
if you find yourself traveling south towards the florida keys, be sure to stop in islamorada...(and maybe just stay). for some happy hour brews, enjoy hog heaven's views of the water at sunset. note, the cocktail shrimp are tasty.
take a trip to robbies to feed the tarpon *careful, those things are vicious* and walk around the various artist tents set up outside of the restaurant and bar.
for a bit of history, take a boat over to indian key - a once inhabited island in the 1840s with a pretty brutal history.
mainly though, just enjoy the sun, water and outdoors. the key's are america's answer to paradise, and you don't even need a passport to get there.