Sarasota has the longest history of the major south Gulf coast cities, with European expeditions dating back to the early 1500s. Fishing camps were established in the mid-18th century, and by 1845 the U.S. Army had established Fort Armistead on Sarasota Bay. Like most of the rest of Florida the town was a rural community defined by nearby ranches and a busy local fishing industry, but it continued to grow, and by 1913 it was incorporated as a city.

Development soon followed during the Florida Land Boom of the 1920s, and with the development of the Tamiami Trail the region was linked to the rest of Florida, making it easier for speculators and potential residents to get to Sarasota. It was during this time that several of the Ringling Brothers began relocating to Sarasota, and the Ringling Brothers Circus established Sarasota as its winter home in 1919.

Like the rest of the state, Sarasota was hit hard by the combination of the imploding Florida real estate market and the Great Depression, but that didn’t keep the city from experiencing rapid growth during the real estate booms that occurred in the 1950s and early 2000s.

Naples, on the other hand, has a history related almost entirely to tourism. Although there was a military post in the area as early as 1837, the town didn’t see any real growth until the late 1920s, in the midst of the Florida Land Boom, when the city was connected to the rest of the state by both railway and the Tamiami Trail.

The city saw rapid expansion during the 1940s and 1950s but suffered devastating losses in 1960 when Hurricane Donna came ashore with winds in excess of 90 mph. Since that time the city, like much of the rest of the region, has seen most of its growth come from the tourism industry.