Named for pirate John Levique who first traveled through a pass created by a hurricane in September 1848, the "Pass," as it is known to locals is tucked along the waterfront on Madeira Beach. Designed to resemble a quaint turn-of-the-century fishing village, it is one of the area's major attractions. More than 100 merchants interspersed along a 1100-foot boardwalk offer boutiques, shops, a variety of restaurants, bars, nightclubs and bistros. You'll also find a local fishing fleet, dolphin watching and shelling tours and more. If you're adventurous you can hold live alligators or go parasailing and jet skiing. For something a little tamer, be sure to book a sunset cruise. Saturday nights feature live bands and drink specials at various bars.