On May 13, 1909, the first the Giro d’Italia (Tour of Italy) kicked off from Loreto Place in Milan. 

The long distance, multi-stage bicycle race covered a long-distance multiple-stage bicycle race, covered a 2,448 kilometer course. 

Giro d’Italia
Issued by San Marino in 1965
Designed by Arseni

 Italian sporting newspaper La Gazzetta dello Sport managed to secure the funds for the first large multi-staged event that would be driven across entire Italia and last for more than 20 days. The first of such events started on 13 May 1909 at Loreto Place in Milan. From there, 127 drivers competed in eight large stages that in total covered 2,448 kilometers. By the end, only 49 riders managed to finish the race, with Italian cyclist Luigi Ganna securing the victory and 5,325 lira or prize money. 
Tour of Italy – History and the Tradition of Giro d’Italia