Erynnis horatius (Horace's Duskywing).
Size: approx. 50 mm. Photo: 05/07/17, 5 pm.

A brownish skipper on a sand pile: Horace's duskywing (Erynnis horatius). There are many similar looking duskywings (17 in the US) but this one has three white/transparent spots on the wings and an accompanying cluster of four smaller spots. The little photo with latana flowers was taken on 06/25/11 at 10 am. 

bug guide (this photo):
bug guide (small photo):

Hylephila phyleus (Fiery Skipper).
Size: approx. 40-50 mm. Photo: 06/25/11, 10 am.

This is another skipper. The German word for skipper is "Dickkopffalter" which means "big head folder". And yes, their heads are big! Based on the color and specific wing patterns, this one looks like a "fiery skipper" (Hylephila phyleus). The caterpillar is green with a black head and lives in the lawn. 
bug guide:

Pyrgus oileus (Tropical Checkered Skipper).
Photo: 08/07/12, noon.

This Tropical Checkered Skipper (Pyrgus oileus) is quite similar to the Checkered Skippers P. communis and albescens (see above). However, it has a blurred wing pattern and a white spot just beyond the cell-end. Also, the white bar is present and enlarged. See the second link for a side by side comparison. 
bug guide (this photo):

Pyrgus communis or albescens (Checkered Skipper).
Size: approx. 30 mm. Photo: 08/21/11, 6 pm.

When I took this photo, this fickle flyer looked like a moth to me. However, it is a Checkered Skipper (Pyrgus communis or albescens). The two species are nearly indistinguishable. In the US, P. communis is a permenant resident south of the 40th parallel. Adults feed on the nectar of white-flowered composites (Asteraceae). 
bug guide (this photo):
Wild Florida Photo:

Thorybes bathyllus (Southern Cloudywing).
Size: approx. 20-30 mm. Photo: 06/15/11, 10 am.

Here's a little neighbor feasting on a jasmine flower. The idea for my humble website was born shortly after taking this photo. Looks really pretty or doesn't it? My first attempt to assign this insect was pretty wrong. Now I believe that it's a 'southern cloudywing' (Thorybes bathyllus). The males are highly territorial. 
bug guide:

Urbanus proteus (Long-Tailed Skipper).
Size: approx. 40-50 mm. Photo: 07/18/11, 9 am.

Long-tailed skipper (Urbanus proteus). Characteristic for this genus is the long, split tail. U. proteus is one of twelve species in this genus. U. procne, for instance looks similar but does not show the greenish color on the main body. 
bug guide (this photo):