Anna Maria Island — Old Florida Beach Town, the City Pier & a Gulf Sunset

A slow, sun-warmed day on the seven-mile barrier island that has resisted high-rises and chain sprawl to keep the flavor of old Florida intact. Anna Maria Island sits just an hour southwest of Tampa across the Sunshine Skyway approaches, a place of pastel cottages, a free open-air trolley, and some of the softest quartz-sand beaches on the Gulf Coast. The day begins in the sleepy northern village of Anna Maria at the historic City Pier and the wild, uncrowded sands of Bean Point, where Tampa Bay meets the Gulf of Mexico. From there it's a lazy trolley ride down Pine Avenue and Bridge Street for lunch and browsing, an afternoon of swimming on the shallow, bathtub-warm Gulf, and finally the whole point of the island — a slow, spectacular sunset over the water.