The tallest surviving gate and tower of the ring of walls built around Florence in 1324, the 60m/200ft Torre San Niccolò may have been designed by Orcagna.
It was the only tower in the walls not given the chop in 1529 when the armies of Charles V (newly allied with the cowardly Medici Pope, Clement VII) attacked the republic of Florence, because of Michelangelo's clever idea of turning San Miniato, the hill overlooking the tower, into a gun fort controlling the surrounding countryside.
It prevented the troops of Charles V from immediately taking the city, pinning them down instead as Florence managed its last heroic but doomed fight for independence.
The distinctive square battlements of the Guelphs, echoing those of the Palazzo Vecchio were added in the 1800s. The lower arch has a 14th-century fresco of the Madonna and St Nicholas and John the Baptist. It has charming views over the city as it contemplates its shorter counterpart, the Torre della Zecca on the right bank of the Arno.
Image by Sailko, GNU Creative Commons License