About 500 years ago the Spaniards brought olives, figs, vinafera grapes, and citrus to Florida. The only one of those that became a major commercial crop here was citrus. Last I knew the only major commercial planting of olives in central Florida (near High Springs as I recall) had gone out of business without pressing a single olive of their own. I have observed small scale plantings in the Highlands County area for a number of years, but have not seen fruit yet. I also believe that Hardee County was testing olives in an attempt to find low chill cultivars. I believe that there is currently a semi-successful olive oil operation in Georgia.
Many people do not realize that avocados have the potential to produce about twice as much oil per acre as olives. The oil has very similar uses and is slightly more expensive. They are also much more reliable bearers here in central Florida.