Naples

For upscale romance and the prettiest, most serene city beach in southwest Florida, come to Naples, the Gulf Coast's answer to Palm Beach. Development along the shoreline has been kept residential. The soft white sand is backed only by narrow dunes and half-hidden mansions. More than that, though, Naples is a cultured, sophisticated town, unabashedly stylish and privileged but also welcoming and fun loving. Families, teens, couture-wearing matrons, middle-aged executives and smartly dressed young couples all mix and mingle as they stroll downtown's 5th Ave on a balmy evening. Travelers sometimes complain that Naples is expensive, but you can spend just as much elsewhere on a less impressive vacation.

The small towns around Naples, Florida are as cool as the main event. Sean Pavone / Getty Images

©Sean Pavone/Getty Images

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