Rinaldo Massoni arrived in Melbourne in 1911 from Lucca, a town to the west of Florence in Italy. He was a surgical instrument maker and practised his trade in Castlemaine, and in Melbourne at an address in Little Bourke Street. He also worked for Ramsays, a company which specialised in medical equipment.
Massoni married Grace Watson, daughter of Nella Watson (nee Panelli) whose father had arrived from Italy in 1888. Through the Panelli family Massoni came into close contact with the world of food and wine. Around 1926 Rinaldo opened a small Italian café in Exhibition Street with Camillo Triaca, a friend from Lucca. The café was called Café Latin (formerly known as Café Bella). In 1927 Massoni left the cafe to open a wine shop in Elgin Street, Carlton, Triaca remained and built Café Latin into a very successful restaurant.
Massoni was drawn back to the city by Samuel Wynn (originally Weintraub), a Jewish immigrant from Poland who needed a manager for the Cafe Denat in Exhibition Street, which Wynn had taken over in 1920 from Calexte Denat. Wynn moved the café to Bourke Street, next door to Edments gift store at 80 Bourke Street. Under Massoni's management the restaurant flourished and the name was changed to Café Florentino.
Massoni bought the lease from Wynn in 1929, but the Wynns continued to live above the restaurant. The restaurant continued to do very well, even during the 1930s Depression. In 1935, the property next-door, formerly Edments' gift store, was bought and renovated to become the new location for Café Florentino. The walls of the upstairs room were decorated with murals by students of Napier Waller and the ornate wrought iron lamps featuring grapes were made by an Italian artist Emilio Gavotto.
In 1933, George Tsindos, a 20 year-old drinks waiter from Cyprus, had joined Café Florentino, he resigned in 1941 for health reasons. Rinaldo Massoni died suddenly in 1941 and the restaurant was kept in trust for his son Leon until he reached his majority in 1946. However, Leon found the workload was too much so in 1950 he approached George Tsindos to form a partnership, which lasted until 1963. During this time the business expanded to include the Cellar Bar and Bistro Grill on the ground floor.
Tsindos bought Massoni out in 1963 and successfully ran the restaurant until 1979. Branco Tocigl took over as proprietor from Tsindos in 1979 and Floyd Podgornik in the late 1980s, followed by Pietro Grossi in 1999.
Today, the restaurant is know as Grossi Florentino and is run by Guy Grossi, the son of Pietro.