Small and simple, Anna Maria Island’s vibe is decidedly more artsy paddleboard-and-cruiser bike than exclusive yacht club.
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 8,500 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.
Bean Point Beach
Though it’s a public beach, the surrounding residential homes keep it quiet. From here, you can walk around the entire island without leaving the sand.
It sits on the water’s edge, and each night patrons compete for the free bottle of champagne given to the diner who guesses the time of sunset. 100 Spring Ave.; 941/778-0444 or sandbar.groupersandwich.com
Rod and Reel Pier
Enjoy a fresh seafood-omelet breakfast and a glimpse of a dolphin or manatee out the window. 875 N Shore Dr., 941/778-1885
Ginny’s and Jane E’s at the Old IGA
Located in the “Old Florida” area of Anna Maria Island, Ginny’s & Jane E’s doubles as a bakery café and island coastal store. 9807 Gulf Drive; 941/778-3170 or annamariacafe.com.
For a dinner splurge, Beach Bistro offers a fine-dining option where flip-flops are still welcome. 6600 Gulf Drive; 941/778-6444 or beachbistro.com.
Take a complimentary trolley to a different beach each day. Don’t be afraid to leave the island, either, for major sporting events in Tampa or Sarasota art festivals within an hour-long drive.
Island Garden Villas
Has six one- or two-bedroom villas, complete with bikes to help you blend in with locals. Rates from $774 to $1250/week; islandgardenvillas.com.