Build sandcastles with the kids, or take a romantic sunset stroll with your sweetie. Anna Maria Island and Longboat Key boast charming beach towns that are a glorious throwback to Old Florida. The blue-green waters of the Gulf of Mexico skirt the sand, creating a colorful canvas of beach towels, umbrellas, pick-up volleyball games and cookouts. Check out the action on a wooden fishing pier, or let your pup cool off at one of three dog-friendly locales.

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