Anna Maria Island was part of the Safety Harbor culture area for many centuries before the arrival of Europeans in Florida.

As Cuban fishermen were the first visitors to the island at the southern mouth of Tampa Bay, the settlement was very soon dominated by nautical types.

[3][4] The first bridge that was built to connect Anna Maria Island to mainland Florida began construction in the summer of 1921.

[8] Legend states that "a Spanish explorer" named the place "Ana Maria Cay" in honor of the Virgin Mary and her mother, Ann.

There are pelicans, multiple types of cranes, herons, feral parrots, sandpipers, osprey, hawks, vultures, seagulls, crows, and a nesting pair of bald eagles.

Marine animals include redfish, snapper, mackerel, black drum, snook, trout, and amberjack.

It was uninhabited until 1960, when a bridge was built joining it to the Holmes Beach section of Anna Maria Island and development began.

Anna Maria Island is served by a free trolley-style bus that runs north and south on Gulf Drive.

[26] The SCAT connects to the trolley at Coquina Beach, at the south end of Anna Maria Island, just before the Longboat Key Bridge.

[30] This success has not been without its downsides of congested traffic, noise, litter and parking complaints during peak tourist seasons.

[31] This influx of visitors has prompted developers to convert many of the original 1950s and 1960s-era houses into short-term rental units, a subject of local controversy.

In the plot "a beautiful movie star travels to Hawaii and finds romance in this South Seas musical.” Anna Maria Island is featured in the Florida band Shinedown's video for "Second Chance".

Anna Maria Island is the setting for the 2016 comedy/drama, Monty Comes Back, written and directed by Bradenton native Thomas John Nudi.

Longtime resident Kathleen Flinn wrote about her family's abrupt move to the island in the 1970s after her dying father fell in love with the place in her book, Burnt Toast Makes You Sing Good (Penguin Random House).