This vehicle in the photo it most probably a Fiat 2800 cabriolet which was used by a Luftwaffe unit in Italy. It had a car body which did not correspond to the production line. Possibly it originated from an independent car body manufacturer.
The car body manufacturer of the shown American looking Fiat 2800 could not be identified so far.
This sporty looking car with a pennant of a general headquarters is a Fiat 2800, too. The photo was made in Italy in 1944.