On October 10, 2018, category 5 Hurricane Michael made landfall at Mexico Beach, generating a nearly 5-m storm surge. The greater landfall area is characteristic of a cuspate headland protruding into the Gulf of Mexico for up to 50 km. The headland is composed of several barrier islands with different orientations fronting a large estuary. The hurricane-impacted areas include densely developed small beachfront communities, modestly to sparsely developed shoreline communities, mostly pristine state parks, and a completely pristine national wildlife refuge. Therefore, Hurricane Michael provides an excellent opportunity to study the impact of an extreme storm over various coastal environments with different degrees of human developments. Because of the shoreline orientation and bathymetry changes induced by the headland, the wave field associated with the hurricane is complicated, with different locations for the highest wave and the landfall site where the surge and wind speed were the greatest. Numerical wave modeling revealed two wave-focusing points along the headland where barrier-island breaching occurred. Beach-dune erosion and impact to infrastructure were examined and compared among various natural–human coastal systems. The magnitude of dune erosion was mostly controlled by the storm wave height and prestorm beach width, but the height of the prestorm dune was not a determining factor. Sedimentological characteristics of storm deposits along the barrier islands, within Apalachicola Bay, and in the surrounding coastal marsh were examined using 116 sediment cores and 40 grab sediment samples. Characteristics of storm deposits and their preservation are described for various subenvironments, including beaches, dunes, interior wetlands, back-barrier bay, and coastal marsh along the landward side of the estuary. The landward penetrations of identifiable sandy overwash deposits were less than 150 m along the barrier islands and less than 30 m along the mainland marshes. These results should have potential implications on paleostorm study.