When we first visited Siena, as part of a sponsored organized tour, we were taken for a walk down the high street straight into a museum, came out 2 hours later and went, more or less, directly back to the bus.
No disrespect to our hosts (one branch of the large and sprawling tree of the Italian Tourism Board), they undoubtedly meant well, but we – all the participants of the tour – agreed that this was almost a textbook example of How Not To Visit A Famous Historical Town. Surely, one could come up with a better alternative.
So when we went back to Siena recently, we tried something else.
What seeing Siena a second time gave us
We started our walk at Piazza del Campo, one of the most soul-stirring views in the world. No picture can catch the feeling when you break through one of the archways in the narrow medieval streets of ancient Siena, and suddenly this enormous central square opens up in front of your eyes.
Renaissance architects certainly knew a thing or two about theatrical effects.
Look for Via Bianchi di Sopra behind the Palazzo Publico and from there, turn right into Via del Moro behind Piazza Tolomei. Follow this street through a left and a right turn but then turn left into Via del Refe Nero and right into Via del Giglio.
Another left turn (into Salvani Provenzano) and one right turn (into Via dei Rossi) later, you will have arrived at the Church of San Francesco, originally built in 1228, only two years after the death of its patron saint and therefore one of the oldest churches in the world devoted to the founder of the Franciscan order.
One devastating fire or ten later, it is today a bit of a hodgepodge of architectural styles but has still, somehow, managed to preserve a sacred grandeur.
Trace back your steps on Via dei Rossi – not minding the curious lady behind the curtains that never seem to twitch …
… and turn right into Via Bianchi di Sopra.
The colourful flags in which Siena’s Old Town appears to be draped for most of the year represent different town wards that compete in the twice-yearly palio on Piazza del Campo.
Curiously, the palio was imposed on Siena by – of all people – the hated Florentines who, following the conquest of their rival city state in 1554, banned the previously popular bull fights and needed something to replace them with.
Turn left into Via Pianigiani. On the left hand side of the street, have a look into the Consorzio Agrario di Siena, a great place for products from the region at reasonable prices. Great for souvenirs, too: do not leave Siena without at least one slice of Panforte, a Christmas pudding for all seasons!
Continue straight until you reach a large roundabout called Piazza Matteotti and turn into Viala Tozzi on its far side.
Turn left into Via Cesare Maccari, walking past the La Lizza gardens until you reach the Fortezza Medica, which was built by the Florentines in the 16th century after Cosimo de Medici’s victory over the Sienese.
Seeing Siena a second time, we discovered the architecture of the fortress givinh us a good taste of the brutality that was very much a part of the Renaissance …
… but also of the age’s delicacy and refinement …
… while, most relevantly for city walkers, presenting fine views of the town from a very pleasant walking route around its walls.
Now make your way through the western part of the Old Town – through Viale dei Mille, Via Fontebranda and Via del Costone – to the Cathedral …
… and back to the Piazza del Campo where we start the second stage of the walk.
Follow Via Giovanni Dupré and turn right into Via Sant’Agata at the charming Contrade de la Onda fountain.
Now turn left into the parking lot to walk around the building in front of you into the Orti dei Tolomei gardens from where you get not only wonderful views of the Old Town …
… but also splendid panoramas of the Tuscan landscape.
Circle back to the town centre by using Via della Diana, Via Ettore Bastianini and Via Stalloreggi for more splendid views of the surrounding countryside.
The walk is not in the least bit strenuous but will take you approx. 4 to 5 hours to complete. It can be easily broken up into two sections (when you return to the town centre).
But here is a tip: do not eat in one of the overpriced establishments that line the Piazza del Campo. Look for something else a little further astray in the Old Town, and if you cannot find anything to your liking, try the Consorzio Agrario di Siena’s fast food section where you will get at least the same quality of a fancy place for a fraction of the price.
Visits to the Fortalezza and the Orti dei Tolomei allow you to enrich your trip to Siena with some counterpoint of wide open spaces and vistas.
Another reason why the two are virtually ideal starting and finishing points for a walk through Siena is that they are located at opposite ends of the city.
Walking from one to the other, you can easily manage to cram in all the famous sites into your itinerary – many of which we did not even mention, such as the historical head office of Monte dei Paschi di Siena, the world’s oldest bank.
We found out about the Fortalezza and the Orti dei Tolomei from the Discover Tuscany blog of Helle Rasmussen which has dedicated one short walk to either destination (the descriptions there also feature a map). Thanks for the tip!
