As a well traveled, Florentine artist, Boscoli gathered much influence and social connection, which in turn carried his own influence into artists after him. He was described as a vibrant personality, almost bizarre, but with a love for art, astrology, music and poetry. He began his training under the late-Mannerist painter, Santi di Tito (1536 – 1602) and was also a member of the Florentine Accademia del Disegno, joining in 1583.
His training there was during a reform of the Mannerist style which encouraged more naturalism. Boscoli developed his own aesthetic within this reform, giving great detail to form and lively representations of his subjects. This definitive style of his closely followed his continuing influence though travels and awareness of the art world.
Additional to a breadth of connections with Italian artists, his time in Rome introduced him to visiting artists from north of the Alps. During this time he was also influenced by the work of Florentine painter Jacopo Zucchi (1541 – 1590), who had trained under Giorgio Vasari (1511 – 1574). Boscoli also befriended an artist well versed in the art world of the time, Federico Zuccari (1542 – 1609), who like Vasari was a critic and historian of the Italian painters.
Boscoli painted frescos in the Chapel della Cella for the sculpture Giovanni Angelo Montorsoli at the Servite Convent in Rome. In 1592 he painted mythological frescoes in the Villa della Seta in Pisa, which was one of his works that continued to show vivid use of light and shade. He painted a series of drawings of the Passion, which were made into engravings and also painted altarpieces throughout Florence. He also painted a number of privately commissioned works, which were nonetheless profane from his work in the cities.
Seven years before his death, Boscoli was still highly active in painting frescoes and altarpieces. These works gave way to a revival of Mannerist style in his art with expressive proportions and forms, something of a departure from his acute naturalist training. He died in Rome shortly thereafter in either 1606 or 1607.