I love a quick weekend trip to South Beach. Only a 2 hour-something flight from JFK, and guaranteed sun and fun (i.e., long dinners, early morning walks on the beach, poolside margaritas, and for me, minimal makeup and hair care).
Traveling to Miami, or any nearby beach destination, means I pack light. I like knowing 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), swimsuits (two, max) and a reliable flat sandal can be re-worn throughout the trip, making packing and getting dressed easy.