The late 70s and 80s saw Hawkwood move his home from the Romagna to Tuscany, within the orbit of Florence; and despite fighting on a number of campaigns, the relationship with Florence deepened.

In 1387 Hawkwood was approached by Giovanni Ubaldini, Padua's military commander, to come and fight against Verona. He agreed, and by March was in the field, facing his enemy by the River Adige near the village of Castagnaro.