Surrounded by the Gulf of Mexico, Tampa Bay, and the Intracoastal Waterway, Anna Maria Island is an easy 1 1/2-hour drive from Tampa. It's only 7 1/2 miles long and less than a mile wide. It boasts not a single towering condo. (No building over three stories is allowed.) The restaurants are delightfully local and extremely good, with few chain restaurants to be found. In other words, you’ve stepped back into the Florida of decades ago.