I love a quick weekend trip to South Beach, Miami. Only a 2 hour and something flight from JFK, and guaranteed sun and fun (i.e., long dinners, early morning walks on the beach, poolside margaritas and guacamole, and for me, minimal makeup and hair care).
When traveling to Miami, or any other nearby beach destination, I always pack light. I like to know exactly what I will wear each night so the entire process is very formulaic. The daytime is spent laying out at the pool, beach or boat, so cover-ups (one or two options) and swimsuits (two, max) can be re-worn throughout the trip, making packing and getting dressed a lot easier.