A good first stop in Siena is the Pinacoteca Nazionale. This houses works charting the progression of Sienese art through the Middle Ages. A lot of gold against the soul.
Medieval Sienese art was overwhelmingly religious in nature. Whereas Florentine art embraced the shift away from static iconography into realistic gestures and expressions (as exemplified by Giotto) and then sparked a Renaissance by looking for sources of inspiration outside the Church, the masters of Siena took the view that if it ain't broke, don't fix it. So on into the 16th century Sienes art featured composed tableaux of saints; the only variation would be whether they were standing or seated. And their recognisable features would remain the same - St Sebastian would be piereced with arrows, St Lawrence would seem quite comfortable posing with the griddle he was martyred on, as would St Catherine of Alexandria with her wheel. Mary Magdalene would always have her box, Francis his stigmata, and Peter his keys. John the Baptist would be in rough furs, St Augustine, in monkish brown robes, St Girolamus in the red of a cardinal. All would be haloed and highlighted with gold. I can't help think that Siena's decline was accentuated with the sheer amount of gold they were using in their paintings. What a tour of these works does give you is the chance to recognise the features of each saint. Continuing, you can play a game, trying to work out who each figure in a triptych is before you read the label: "That's St Bartholomew - that's St Anthony of Padua - that's St Anthony Abbot". Of course, on occassion they would throw in one you had never heard of to fox you - St Pantaleone anybody? This prepares you to get the most out of the other iconographic works you will see around Siena.
Artists of the Sienese school on display here include Duccio di Buoninsegna, Simone Martini, and Pietro and Ambrogio Lorenzetti. One work in particular that I loved was Martini's picture of the Blessed Agostino Novello. Agostino may not be a saint, but he is depicted swooping down like Superman to catch a child who has fallen from a balcony or resue a man thrown from his horse. I had to get a postcard of that picture from the gift shop.
Moving down from the third floor, where you start a chronological tour, you come to later, darker works after Siena had embraced realism. Strangely, I wasn't so keen on this stuff. One painter who cropped up quite a bit was called 'Sodoma'. Well, he wasn't, but the famous art historian Vasari didn't like him and gave him this rather unflattering nickname, which stuck. Mind you, in a Deposition he does have a soldier wearing *very* close-fitting Boystown shorts...
There are maybe no outstandingly great works in Siena's Pinacoteca; it is a mere shadow of a shadow of Florence's Uffizi. However the works, even if somewhat samey, are pretty jolly. Plus, they enable you to recognise the subjects of other works you will see on your stay in Siena, and is worthwhile on that basis.
From journal Sainted Siena