Siena in 3 days

Siena Cathedral (the Duomo di Siena — dedicated to the Assumption of Mary; begun 1215, the current building substantially completed 1380; built in alternating bands of black and white marble (the Sienese colours) in the Italian Gothic style; the façade is by Giovanni Pisano (1285-1296) — the finest Italian Gothic sculptural programme on any cathedral façade; the interior: the most extraordinary cathedral floor in Europe — 56 marble intarsia (inlay) panels covering 3,000 m² depicting biblical scenes, allegories, sibyls, and historical subjects (the programme was executed by dozens of artists from 1372 to 1547; including panels by Pinturicchio, Beccafumi and Matteo di Giovanni); the floor is covered for most of the year for preservation — it is uncovered only mid-August to October 27 for the "Opera della Metropolitana" season).

The Piccolomini Library (the chapel-library built 1492 within the Siena Cathedral by Cardinal Francesco Todeschini Piccolomini (later Pope Pius III) to house the library of his uncle Pope Pius II (Aeneas Silvius Piccolomini, 1405-1464 — the first pope to write a personal memoir, the Commentarii; the first pope to visit the ruins of Rome as a tourist rather than a pilgrim; the most intellectually engaged pope of the 15th century); the library walls are covered with 10 large fresco panels by Pinturicchio and his workshop (1502-1508) depicting the life of Pope Pius II — the finest narrative fresco cycle in central Italy outside of Raphael's Vatican Stanze; the Graces (the Three Graces — the Roman marble sculpture at the centre of the room, formerly in the Piccolomini library and one of the great classical antiquities of the Renaissance).

The Facciatone (the "Big Façade" — the wall of the nave of the Nuovo Duomo, the New Cathedral that Siena began building in 1339 to create the largest cathedral in the world; the nave of the new cathedral would have been 90 m long (the current cathedral would have become just the transept); construction stopped in 1348 when the Black Death killed half the population of Siena (the catastrophic population collapse of the bubonic plague: 30,000 of Siena's 50,000 inhabitants dead within months; the Black Death arrived in Siena in May 1348; the construction never resumed; the incomplete façade wall (the Facciatone) still stands, and visitors can climb to the top for the finest panoramic view of the Piazza del Campo and the complete Siena roofscape from an elevated position).

The Museo dell'Opera del Duomo (the Cathedral Museum, in the abandoned nave of the new cathedral — the collection of artworks removed from the cathedral for conservation: the most significant single object is Duccio di Buoninsegna's Maestà (1308-1311 — the double-sided altarpiece (3.5 m × 4.6 m) painted for the main altar of Siena Cathedral; one of the most important paintings in the history of Western art — the moment when Byzantine flatness began to give way to the three-dimensionality and emotional naturalism of the proto-Renaissance; the Virgin and Child are surrounded by angels and saints on the front; the Passion of Christ in 26 panels on the back; the back panels (the Passion scenes) are the most spatially advanced paintings in Europe of their date); the original sculptures by Giovanni Pisano from the cathedral façade (displayed at eye level, where the detail invisible from the cathedral exterior is revealed).

Val d'Orcia (the Orcia River valley, 50-80 km south of Siena — the landscape that defines the Tuscan visual aesthetic: the rolling clay hills (the Crete Senesi), the white unpaved roads (strade bianche), the isolated cypress trees on hilltops, the fortified medieval hill towns (Pienza, Montalcino, Radicofani), the distant view of Monte Amiata; UNESCO World Heritage 2004 (the first purely agricultural and pastoral landscape to receive this designation); the Val d'Orcia was the most painted landscape in Renaissance Siena — the background landscapes of Duccio, Simone Martini and the Lorenzetti brothers use the same cypress-on-hill composition that photographers still photograph; the specific viewpoint above Pienza (the San Quirico d'Orcia hill town) gives the most classic Val d'Orcia panorama).

Pienza (48 km south of Siena — the Renaissance "ideal city" built in 4 years (1459-1462) by Pope Pius II on the site of the village of Corsignano where he was born; Pius commissioned the Florentine architect Bernardo Rossellino to rebuild the entire town centre according to Renaissance urban planning principles: the cathedral (Pienza Cathedral, 1462, the first Renaissance cathedral in Tuscany — with the German hall church plan that Pius requested having seen Gothic German churches on his travels as a Cardinal), the Palazzo Piccolomini, the Palazzo Comunale and the Bishop's Palace arranged around the Piazza Pio II; Pius famously said he built Pienza "with such love that I cannot look at it without feeling pain that I must one day leave it"; UNESCO World Heritage 1996; the Val d'Orcia view from the Pienza garden terrace is the finest single viewpoint in all of Tuscany).

Montepulciano (67 km south of Siena — the hilltop town of the Vino Nobile di Montepulciano (the most aristocratic Tuscan red wine after Brunello di Montalcino and Chianti Classico; the Nobile is made from the Prugnolo Gentile grape (the local clone of Sangiovese); the Renaissance palaces of the Via Graccano — the main street of Montepulciano lined with the finest 16th-century aristocratic architecture in Tuscany outside Florence; the Cantina Contucci (the underground winery beneath the Palazzo Contucci at the top of the main street — one of the oldest continuously operating wine estates in Italy; the underground cellar with the old barrique barrels carved into the rock; tasting of the Vino Nobile ); the Piazza Grande (the main square of Montepulciano with the Palazzo Comunale (modelled on the Palazzo della Signoria in Florence) and the unfinished Duomo of San Biagio below the town).

San Galgano (38 km west of Siena — the 13th-century Cistercian Gothic abbey now open to the sky; the monastery was abandoned in the 18th century and the roof collapsed in 1786; the nave walls and Gothic arches still stand to their full height, framing a rectangle of Tuscan sky above the grass-covered floor — the most atmospheric roofless Gothic ruin in Italy; the Rotonda di Montesiepi above the abbey (the round Romanesque chapel, 1185, built on the hill where Galgano Guidotti — a 12th-century Tuscan knight — plunged his sword into a rock to renounce violence; the original sword is still embedded in the rock, protected by perspex; the relic is the basis of the Arthurian "sword in the stone" legend according to some scholars); the Lorenzetti-attributed frescoes in the rotunda chapel.