First settled in the time of the Etruscans (c. 900–400 BC) Siena, located in the Italian region of Tuscany, is renowned for its cuisine, art, museums, winding streets, majestic, medieval buildings and the Palio horse race.
Day 1: Architecture
Siena is a city for exploring in foot. It's small – if a little confusing given that the streets tend to circle around the central piazza, and cars are not allowed in the historic center. Begin by orienting yourself in the heart of the city: the Piazza del Campo. Admire the uniformity of the palazzos ringing the square, the marble fountain Fonte Gaia, and the magnificent city hall, Palazzo Pubblico and its bell tower Torre del Mangia.
To really get a sense of the city's layout, climb the 100m tower for a bird's eye view. Head inside the Palazzo Pubblico and explore the Museo Civico, admiring the many frescoes including Lorenzetti's lesson, Allegories of Good and Bad Government. After lunch head for that other great example of Tuscan Gothic architecture, the Duomo.
Siena's cathedral is one of Italy's great churches and there's plenty to explore including the famous mosaic, floor, the crypt, the Libreria Piccolomini (Pope Pius II's library), the baptistry, and the next door Nuovo Duomo (now the Museo dell'Opera Metropolitana) which was the only section built of an ambitious plan to double the size of the Duomo; the egos behind this concept were only stopped by the plague of 1348 which wiped out more than half the city's inhabitants.
Another church you must visit is the Chiesa di San Domenico. This is where Saint Catherine took her vows before going on to become a patron saint of Italy. While she died and is buried in Rome, her head made the pilgrimage back here and is above the altar. Her thumb is also here, in a small glass box to the right of her chapel.
Day 2: Art
Siena has one of Italy's best art galleries: Pinacoteca Nazionale. It's in the 15th century Palazzo Buonsignori and has some of the best Sienese art of the 14th and 15th centuries, as well as a vast collection of paintings from northern Europe, including Durer. There is also an extensive sculpture collection.
Opposite the Duomo is another center for art, the Santa Maria dell Scala. Formerly one of the oldest hospitals in Europe, set up by the priests of the Duomo to house pilgrims headed for Rome and take in abandoned children, the building is now a focus for art. Some of the best pieces are the frescoes commissioned by wealthy patrons during the 15th century – in particular head to the fourth floor for those depicting the hospital's history, in the Sala dei Pellegrinaio.
The hospital is also home to the Archeological Museum, a Children's Museum and the Briganti Book and Photo Library.
Day 3: Out of Town
Tuscany is not huge but it is rich in history and beauty. If you've ever had enough of what Siena itself has to offer, think about a day trip to Florence to see the differences between these arch rivals in art, architecture and commerce. Siena largely wins for the Gothic, Florence for the Renaissance.
A little closer is the town of San Gimignano, famous for its towers. It once had 72; the 14 that remain still make this walled medieval town an impressive sight. It's also smaller and quieter than Siena or Florence.
Another fierce rivalry back in the day was between San Gimignano and Volterra, also nearby and worth visiting for its archeological sites, including an excellent Etruscan Museum and a Roman bathhouse and theatre.