Around 1865, the Italian urban designer Giuseppe Poggi (1811-1901) began constructing the southern ring way around Florence. The so-called viale dei Colli runs on the former old city walls that Poggi was commissioned to demolish to meet the needs of the then-expanding modern city. Winding through the southern hills, the scenic road is brought to a climax in the Piazzale Michelangelo, the wide terrace with a monument in the middle, containing bronze copies of the famous marble sculptures which Michelangelo had made during his Florentine period. From there a beautiful panoramic view unfolds. One can see at a glance the Tuscan city along the Arno river practically in its Renaissance state as the Medici family had left it a long time ago. Actually, even now the later nineteenth-century urban sprawl seems almost invisible, or appears no more than a blur around the historic inner city at the most. Since its inauguration in 1869, hardly anyone who travels to Florence will miss a visit to the Piazzale to enjoy the splendid view on the city. In this chapter, the panoramic view of Florence is studied as an iconic site, that is, a privileged point of reference within the collective remembrance of a specific historical period, in this case the Renaissance. By investigating the way the city was depicted by different artists, it is argued that the late eighteenth- and nineteenth-century interpretation of Renaissance Florence played a key role in raising the panoramic view of the city to an iconic status.