In an idealized vision of Florence, Carnival takes on the witty expression and intense gaze of Lorenzo de’ Medici, who, around 1490, wrote the famous carnival song dedicated to Bacchus and Ariadne. The song, intended for a choir and accompanied by music, included the memorable refrain: “Chi vuol essere lieto, sia: di doman non c’è certezza” (“Let those who want to be happy, be so: there is no certainty in tomorrow”).

Florence’s tradition of floats, called trionfi (made from wood and jute), brought lively, colorful celebrations in the days leading up to Lent, with commoners and nobles alike filling the streets. Masked young noblemen often joined in, playfully chasing one another through the crowd and tossing rag balls at passersby or into artisans’ workshops, trying to force the bosses to let workers enjoy the Carnival fun. This game sparked surprise and amusement among those caught up in it.

By the second half of the 15th century, the game that would later become calcio storico was so popular among young people of all social classes that it was played in nearly every street and square. The game was eventually formalized and allowed in the city’s main squares, especially during Carnival, when everyday rules were relaxed. The most legendary calcio storico match took place on 17 February 1530, when 54 noblemen played to mock the troops of Emperor Charles V, who had been besieging the city for months. They played in Santa Croce, ensuring the enemy, camped on the surrounding hills, could watch. Musicians played festive music, and despite their exhaustion, the noblemen took the field with pride.

During the Lorraine rule in Tuscany, the tradition of chariot parades, parties, and games continued. Carriage rides, theatre balls (beginning with Teatro La Pergola, which also premiered operas and comedies for the occasion), and lavish masked gatherings in Piazza Santa Croce were held in the afternoons and evenings. The theatres stayed open longer and became ideal venues for dance parties, while similar events were also hosted in private residences, noble palaces, and by foreign diplomats. In grand halls, guests danced the quadrille, minuet, and gavotte, while in the squares and on farmyards, the music of the trescone, carola, and salterello filled the air.

At the end of the 18th century, the character of Stenterello was born at the Teatro del Cocomero, thanks to the Florentine actor Luigi del Buono. Thin from the hardships of his life, pale, shaky, a poor commoner, yet ironic and clever, Stenterello embodies the man who always manages to escape trouble while criticizing and challenging authority—capturing the essence of the Florentine spirit of his time. His yellow waistcoat bears two symbolic markers: the number 28, a reference in Florence to men betrayed by their wives, and the phrase posa piano along the edge, indicating a calm demeanor that hides his knack for avoiding hard work. Stenterello’s mismatched knee-high socks and love for wine are his trademarks, and according to Pellegrino Artusi, he had a particular fondness for frittelle di tondone—lemon-scented fritters with malaga grapes, as described in recipe 181.

In the 19th and early 20th centuries, public balls were held under the loggias of the Mercato Nuovo and at the Loggia dei Lanzi, where even nobles and lords, upon arriving, could become the targets of playful jokes and laughter. The Great War brought a period of reflection to Florence, and it was only after 1918 that masquerades in wealthy residences resumed, along with a renewed desire to dress up, similar to the revival in Venice. Meanwhile, the grand allegorical floats of masked parades shifted almost entirely to Viareggio, where in 1921, the first music-accompanied parade took place along the Viali a Mare.

However, 19th-century Florence remains known for hosting some of the most spectacular carnivals. In 1886 and 1888, the former Ghetto, which had been emptied of its inhabitants in 1882, was transformed—first into a vision of Baghdad and later into a “Chinese” city. Artists and set designers created entire streets, houses, shops, and squares, turning the area into a city within a city. Once the festivities ended, the furnishings were auctioned off to support families in need.