Giotto Paints the Crucifixion of Rimini for the Santa Maria Novella Church

According to Vasari, Giotto's earliest works were for the Dominicans at Santa Maria Novella.

These include a fresco of the Annunciation and the enormous suspended Crucifix which is about 5 metres high. It has been dated around 1290 and is therefore contemporary with the Assisi frescoes.

Other early works are the Madonna and Child panel now in the Diocesan Museum of Santo Stefano al Ponte, Florence, and the signed panel of the Stigmata of St. Francis, from Pisa and now in the Louvre.

In 1287, at the age of about 20, Giotto married Ricevuta di Lapo del Pela, known as "Ciuta". The couple had numerous children, (perhaps as many as eight) one of whom, Francesco, became a painter. Giotto worked in Rome in 1297–1300, but few traces of his presence there remain today. The Basilica of San Giovanni in Laterano houses a small portion of a fresco cycle, painted for the Jubilee of 1300 called by Boniface VIII. In this period he also painted the Badia Polyptych, now in the Uffizi, Florence.

Giotto's fame as a painter spread. He was called to work in Padua, and also in Rimini, where today only a Crucifix remains in the Church of St. Francis, painted before 1309. This work influenced the rise of the Riminese school of Giovanni and Pietro da Rimini. According to documents of 1301 and 1304, Giotto by this time possessed large estates in Florence, and it is probable that he was already leading a large workshop and receiving commissions from throughout Italy.