The island-wide speed limit never tops 35 mph, so bicyclists sometimes move at too fast a pace for this town on a tiny, white-sand sliver about 50 miles south of Tampa. Anna Maria, on the north end of the 7- by 2-mile island, holds 1,800 people on its quaint seaside point. (The entire island has only 8,800 residents.)
There are no high-rise condos or greasy golden arches. Gulf Drive cuts down the center, and canals branch off from the interior, creating a plethora of water-accessed homes. Instead of a car, it’s more likely you’ll use your bike, kayak, or flip-flops. You know the nights are quiet when turtles choose your beach to lay their eggs.
There’s only one course on the island, the private Key Royale Club, but this is Florida after all, so there’s plenty of public and semiprivate golf to be had up to a half hour away on the mainland. Anna Maria’s vibe is decidedly more artsy paddleboard-and-cruiser bike than exclusive yacht club.