Where did the Italians first go?

The Italians first went to the Caribbean in their voyages to the New World. It indeed was in the Caribbean that Cristoforo Colombo [c. 1451-May 20, 1506] first made landfall. On October 12th, he stood on the sands of Hispaniola, which we today know as the island that's shared by Haiti and the Dominican Republic. But on subsequent voyages, they kept expanding their areas of settlement interest. So they ultimately ended up forming settlements from which modern Italian communities are descended, throughout the breadth and width of the Americas.