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Historian Hans Baron referred to it as the crisis of the Early Renaissance.  In 1390, war broke out between Florence and Milan.   At stake was the possibility of Italy becoming a unified kingdom or remaining fractured into independent city-states.  Florence faced significant challenges and setbacks in its efforts to resist Milanese expansion.  Ultimately, Florence found itself isolated and vulnerable, facing the powerful forces of Gian Galeazzo Visconti.  However, Gian Galeazzo's death due to the plague in 1402 marked a turning point.  His death allowed for the return of a balance of power among independent regional states in north and central Italy.

Map of Florence from Paul Strathern's "The Medici: Godfathers of the Renaissance."
Map of Florence (podpage.com)

Resources:
The History of the Florentine People by Leonardo Bruni

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Intro Music: Hayden Symphony #39
Outro Music: Vivaldi Concerto for Mandolin and Strings in D