Prior to 1921, the only way to access the island was by boat as there were no bridges. The first bridge was built in 1921 through the efforts of Thomas Phillips and Jack DeLysle who formed the Crescent Beach Bridge and Road Company to get the bridge built so they could develop the island.
In 1926, a devastating hurricane washed away the first bridge and created San Carlos Island by opening the aptly named "Hurricane Pass" and creating the need for another bridge to reach the island. The second drawbridge replaced the first and was fondly known as the "Swing Bridge."
In 1978 the swing bridge was removed to make way for the current Matanzas Pass "Skybridge." By 1979 the present bridge was completed, welcoming all to Estero Island's paradise.