The first bridge was built in 1925 by John Ringling, who owned large tracts of land on both Lido and Longboat Keys. He wanted to develop the islands and financed the cost of the bridge at the cost of approximately $750,000, equivalent to $13 million in 2023[5], to connect the islands with the mainland.[6] The ornate bridge opened for traffic on February 7, 1926. It was labeled "one of the greatest engineering accomplishments in the South” by the Sarasota Herald, which also proclaimed, “There are no words adequate with which to express our appreciation.”[4][7] Ringling donated the bridge to the city in 1927.
Around 1950, the first bridge began to show that it could not adequately handle increased traffic to the islands. In 1951, the State Road Department opted to replace the bridge with a four-lane drawbridge, which was completed and opened to traffic in 1959. The drawbridge was built for $20 million, and the original bridge was demolished.
Around 2000, the drawbridge began to suffer the same fate as its predecessor. With the drawbridge opening as many as 18 times a day, it was unable to handle increasing amounts of traffic. To remedy the situation, construction began on the current high-span bridge in 2001. The 65-foot (20 m) tall bridge opened for traffic in 2003 for $68 million. Landscaping around the bridge was financed by private donors.[7]