Loop from Florence

01 Museum

Galleria dell'Accademia

Michelangelo's David left Piazza della Signoria in 1872 to escape the open air, and has since held pride of place in this museum founded in 1784 alongside the Academy of Fine Arts. Approach it through a gallery where the Prisoners, barely freed from the block, seem to struggle against the stone. The gold grounds of the Tuscan primitives round off the visit.

02 Museum

Florence Cathedral

Cattedrale di Santa Maria del Fiore

Begun in 1296 by Arnolfo di Cambio, the cathedral was not consecrated until 1436, once Brunelleschi's dome, the largest in masonry, had been closed. Admire its façade of white, green and pink marble, which in fact dates only from 1887. Inside the dome, Vasari and Zuccari painted 3,600 square metres of Last Judgement.

03 Museum

Uffizi

Palazzo degli Uffizi

Walk along the narrow courtyard that Giorgio Vasari designed in 1560 for Cosimo I, bringing together thirteen Florentine magistracies between Piazza della Signoria and the Arno. These offices now house the largest collection of Botticelli and Raphael. From the wing on the river, the eye races towards the Ponte Vecchio.

04 Monument

Ponte Vecchio

Rebuilt between 1339 and 1345 after the flood of 1333, this three-arched bridge has been the oldest in Florence since 1944. Cross it on foot, between the little shops suspended above the Arno. Higher up runs the Vasari Corridor, which links Palazzo Vecchio to Palazzo Pitti for Cosimo I de' Medici.

05 Monument

Piazzale Michelangelo

Climb up from San Niccolò by the ramps of Giuseppe Poggi, the architect who laid out this terrace from 1869, when Florence was the capital. At the top, a bronze David watches over the view: the Ponte Vecchio, the Palazzo Vecchio, the dome of the Duomo and the hills of Fiesole. Between these monuments spread the city's tiled roofs.

06 Church

Badia di Passignano

Abbazia di San Michele Arcangelo a Passignano

Amid the Chianti hills, the abbey of Passignano looks more like a castle than a monastery, with its 15th-century quadrangular walls and corner towers. Stop to read its silhouette, where 19th-century neo-Gothic additions blend with the old walls. St John Gualbert, the Vallombrosan reformer, died here in 1073.

07 Village

Greve in Chianti

On the Chiantigiana road, between Florence and Siena, Greve grew up around its market square, at a crossroads of paths. The square, an elongated triangle lined with arcades, has at its centre the statue of the navigator Giovanni da Verrazzano and closes on the church of Santa Croce. Afterwards, climb up to the fortified village of Montefioralle, on which Greve once depended.

08 Village

Castellina in Chianti

You arrive at 578 metres, on the outpost Florence held against Siena in the heart of Chianti. In 1478, Giuliano da Sangallo led the defence here against Francesco di Giorgio Martini, in vain. Close by, the Etruscan tumulus of Montecalvario dates from the seventh and sixth centuries BC.

09 Museum

Museo d'arte sacra del Chianti

10 Castle

Castello di Brolio

Look above the vines at this castle of the Ricasoli, Florence's last outpost facing Siena, taken by the Sienese in 1252 and returned in 1478. In 1835, Bettino Ricasoli had the old fortress clad in neo-Gothic brick, with Tudor windows and crenellated turrets. It was here, in 1874, that he set the blend of Chianti Classico.

11 Church

Badia of Santi Salvatore e Cirino

Abbazia dei Santi Salvatore e Cirino

Stop at Abbadia a Isola, a stage on the Via Francigena that Sigeric of Canterbury recorded in 994. Ava, widow of a lord of Staggia, founded a monastery here in 1001, whose Romanesque church, consecrated in 1173, inspired the neighbouring parish churches. Protected by popes and emperors, the abbey swore allegiance to Siena in 1215.

12 Village

San Gimignano

In the 14th century, San Gimignano had 72 towers, raised by families grown rich notably on saffron sold as far as Syria and Egypt. Fourteen still stand, and the decline that followed the plague of 1348 froze the town in its medieval form. Watch them rise from afar above the Val d'Elsa.

13 Village

Volterra

Perched at 531 metres between the valleys of the Cecina and the Era, Volterra was one of the great Etruscan cities under the name Velathri. Walk along what remains of its walls and pass beneath the Porta all'Arco, whose carved heads have kept watch since Etruscan times. In the town's workshops, alabaster is still worked, as it has been since the Etruscans.

14 Monument

Piazza del Campo

Sit down on the brick of this shell-shaped square sloping towards the Palazzo Pubblico, divided into nine sections by white strips. Above rises the Torre del Mangia, built from 1325 to 1344, and Jacopo della Quercia adorned the Fonte Gaia. Twice a year, the Palio sends its horses racing around the square.

15 Church

Siena Cathedral

Duomo di Siena

Striped with white and black marble, Siena Cathedral bears on its façade the work of Giovanni Pisano, master of the works from 1284 to around 1297. On Piazza Iacopo della Quercia, see the facciatone rise up, the unfinished wall of an outsized extension abandoned in 1357, after the plague. It speaks of the ambition of a city then at its peak.

16 Church

Collegiata di Sant'Agata

A wide staircase climbs to the travertine façade of Sant'Agata, adorned with a rose window and three blind pointed arches. Walk round the building to the 11th-century Romanesque apse, topped by an octagonal tiburio and a terracotta lantern. In the Gothic nave with its exposed timber roof, an Enthroned Virgin by Francesco Vanni, painted around 1600, keeps watch.

17 Abbey

Abbazia di Monte Oliveto Maggiore

In 1313, the Sienese nobleman Bernardo Tolomei withdrew to this wooded height in the Crete Senesi to live as a hermit. A red-brick tower guards the entrance, then an avenue of cypresses leads to the church. In the great cloister, follow the life of Saint Benedict painted by Luca Signorelli and Il Sodoma.

18 Village

Montalcino

Montalcino, whose vineyards produce Brunello, holds its hill at the end of the Val d'Orcia and appears in a deed as early as 814. Siena besieged it for sixteen months from 1199, and the town rose up again and again. Follow its high walkways, from which the view plunges into the valleys of the Ombrone and the Asso.

19 Abbey

Abbey of Sant'Antimo

Abbazia di Sant'Antimo

Near Castelnuovo dell'Abate, the abbey of Sant'Antimo owes its great church to Abbot Guidone, who began it in 1118, calling in architects from France. Cluny served as the model for this Romanesque church in southern Tuscany. On the steps of the high altar, look for the engraved deed of donation known as the Carta Lapidaria.

20 Church

Collegiata dei Santi Quirico e Giulitta

Along the Via Francigena, the collegiate church opens a portal of 1288 attributed to Giovanni Pisano. Linger above all at the Lombard-style main entrance, with its knotted columns resting on lions and two facing crocodiles on the architrave. Inside glows a gold-ground altarpiece painted by Sano di Pietro around 1470.

21 Village

Bagno Vignoni

Gaze at the great pool of hot water that serves as the square at the heart of this Val d'Orcia hamlet. The Etruscans already knew these springs, and Tarkovsky shot part of Nostalghia here. Below the terrace, the water tumbles towards old medieval mills partly carved into the limestone.

22 Village

Pienza

Pienza was still called Corsignano when Enea Silvio Piccolomini, who had become Pope Pius II, decided to make it an ideal city and entrusted the work to Bernardo Rossellino. Stand in the centre of Piazza Pio II, between the cathedral, Palazzo Piccolomini and Palazzo Comunale. The pope's death halted the momentum, and the town has changed little since.

23 Church

San Biagio, Montepulciano

Chiesa di San Biagio

Standing alone outside Montepulciano, the church of San Biagio raises its travertine volumes on a Greek cross designed by Antonio da Sangallo the Elder. Begun in 1518, it received only one of the two planned bell towers, the other halted at its base. Follow this bell tower from one order to the next, Tuscan to Corinthian, up to its pyramidal spire.

24 Village

Montepulciano

Perched at 605 metres between the Valdichiana and the Val d'Orcia, Montepulciano stretches out in an S shape within three rings of walls. Wander its lanes to pick out the palazzi and churches built here in the 16th century by Sangallo the Elder, Vignola or Peruzzi. All around, the vineyards yield Vino Nobile, and the town gave its name to the poet Poliziano.