You can't miss this quirky piece of island history right on Pine Avenue. The Old City Jail is a fantastic photo op and a quick, fun stop that tells a great story about Anna Maria's early days. Built in 1927 to sober up local rowdies with the help of mosquitos, the roofless structure is now one of the most photographed spots around. It’s part of the Anna Maria Island Historical Society grounds, so you can easily pair it with a visit to the main museum next door.