Naples has a well-deserved reputation as a play place for the old and wealthy. But it can also provide a welcome break from the general chaos of Miami. Make the snore-inducing drive across Alligator Alley, and you can spend the day lounging in the sugar-soft sand of the city's much quieter beaches. Head to the downtown strip of Fifth Avenue South to shop at the district's many clothing boutiques, drop by Naples Paddleboard to rent a kayak or paddleboard (rental prices start at $30 per hour), or hit the Naples Beach Brewery to sample the local beer. Grab dinner at the beachfront Turtle Club (be sure to try the $15 famous oysters "Turtlefeller"); then make your way to the Naples Beach Club to take in one of the best parts of Southwest Florida coast: the sunset.