Discover the landscapes, ancient settlements, and Renaissance villas surrounding Florence. This guide highlights the main historical sites around the city, including Fiesole, Settignano, the Bologna road, and the Medici villas of Careggi and Poggio a Caiano.

Fiesole: Ancient City Above Florence

Fiesole sits on a hill north of Florence and offers panoramic views, Etruscan ruins, Roman remains, and medieval architecture.

Dominican Convent of Fiesole

Fra Angelico entered the Dominican order here and later became prior. Notable artworks preserved include:

• A Madonna by Fra Angelico with background by Lorenzo di Credi
• A Baptism of Christ by Lorenzo di Credi
• An Adoration of the Magi designed by Andrea del Sarto and completed by Sogliani

Badia di Fiesole

Rebuilt by Brunelleschi for Cosimo de’ Medici, it became the center of Marsilio Ficino’s Platonic Academy.

Historical highlights:

• Giovanni de’ Medici received the cardinalate here (1492)
• Giuliano, Duke of Nemours, died here in 1516
• Villa Mozzi nearby was the original target of the Pazzi conspiracy

Etruscan and Roman Fiesole

Visitors can explore:

• Etruscan walls
• A Roman amphitheater
• The Romanesque Cathedral with works by Mino da Fiesole, Andrea Ferrucci, and the Della Robbia family

From the Franciscan convent on the ancient acropolis, visitors enjoy expansive views of Florence.

Settignano and Literary Connections

South of Fiesole lie Ponte a Mensola and Settignano, birthplace of Desiderio da Settignano and early home of Michelangelo. Nearby villas such as Poggio Gherardo and Villa Palmieri are associated with Boccaccio’s Decameron.

The Bologna Road: Medieval Borders and the Failed Return of 1304

The road northwest of Fiesole toward Bologna passes through Trespiano, once the northern boundary of Florence.

The Exiled Attempt of 1304

In July 1304, the Bianchi and Ghibellines gathered at La Lastra, attempting to reenter Florence. Chronicler Dino Compagni describes their progress and their brief occupation of the Porta degli Spadai before they were repelled near the cathedral.

Dante, already separated from the faction, took no part in the attempt.

Medici Villas: Careggi, Petraia, and Castello

Villa Medicea di Careggi

Designed by Michelozzo for Cosimo de’ Medici, Careggi became a center of Renaissance philosophy.

Important events:

• Cosimo died here while listening to Ficino reading Plato
• Piero de’ Medici was ambushed nearby in 1466
• Under Lorenzo the Magnificent, Careggi hosted the Neo-Platonic Circle
• Lorenzo died here in 1492

Nearby villas include La Petraia and Castello, major residences of the Medici grand dukes.

Poggio a Caiano: The Medici Villa at the Foot of the Apennines

Designed by Giuliano da Sangallo for Lorenzo the Magnificent, the Villa Reale of Poggio a Caiano stands at the beginning of the Apennine slopes.

A Hub of Culture and Politics

Notable associations:

• Lorenzo wrote Ambra and Caccia col Falcone here
• Emperor Charles V visited in 1536
• Grand Duke Francesco I and Bianca Cappello died here in 1587

Fresco Cycle in the Great Hall

The main hall contains frescoes on Roman history, serving as political allegories for the Medici.

Artists: Andrea del Sarto, Francia Bigio, Pontormo, Alessandro Allori.

Main scenes:

• Triumph of Cicero
• Caesar Receiving Tribute from Egypt, including Lorenzo’s famous giraffe
• Mythological works by Pontormo and Allori

Scenic Routes Around Florence

Beyond Poggio a Caiano, the road climbs to a hilltop church overlooking:

• Florence and the Arno plain
• The Villa Reale below
• The city of Prato
• The rising Apennines

This is one of the most beautiful panoramic viewpoints in the Florentine countryside.