Siena

Distance

40.5 km

Time

about 11.5 hours

Streets

223

Steps

32 streets with steps

Start point

Cattedrale di Santa Maria Assunta

Phone needed while walking

no

Works offline

yes

Expires

never

Landmarks

What I would eat first.

Landmarks are fruit. The bigger the sight, the bigger the bonus.

• Cattedrale di Santa Maria Assunta 1,500 points

  Black and white in bands, all the way up and all the way in: this building is wearing the city's shield. It sits on the flat crown of the oldest hill, so you climb to it from wherever you start. Then walk round the right flank and find an arcade that begins and ends in mid air. The city meant to set a far bigger nave at right angles to this one and got as far as a single wall. That wall has the best view in town.

• Piazza Giacomo Matteotti 500 points

  The north end of the level, and the exact spot where Siena stops being medieval and starts being a place with buses. Broad, straight, flat, and the last easy walking you get before the lanes take you back. I cross it quickly. Everything I actually want to eat is downhill from here.

• Piazza Santo Spirito 500 points

  The eastern edge of the level, up on the Valdimontone ridge, where the lanes stop being a crush and open just enough for a bench. There is a dome here you cannot see at all until you are standing next to it. Behind the square, the level runs out.

• Porta Romana 500 points

  The south-eastern foot of the level, and the lowest ground you will stand on all day. Everything above you is the way home. Step through, turn round, and look at what you are about to climb: from out here it is all city and all uphill.

• Torre del Mangia 500 points

  Four hundred steps and no lift, in a shaft barely wider than the stair inside it. No one has ever made this easier, and I approve of that. From the terrace the three hills of the Old Town read as three hills again, and the shell of brick at the foot of it is the flattest ground for miles.

• Mercato delle Merci 250 points

  The one point on this level that is an event rather than a building. Come on market morning and the whole width of the road is food, laid out under plane trees on the western rim, next to the open ground of La Lizza. Come on any other morning and it is a very good road with plane trees on it. I take what I get.

• Mura di Siena 250 points

  Brick, and not a circle. Follow it from outside and the trick shows itself: it is a contour line. Where the ground fell away they let the ground do the work, and where it did not they built. You meet it on the south and west rim of the level, and there the house fronts end and open country starts in one step.

• Piazza San Francesco 250 points

  The north-east shoulder of the level. Big, plain, brick, open on one side, and it looks like a place that mislaid a few of its own walls. Walk to the low edge and the country east of the city drops away in front of you. The stairs down from here are worth the detour on their own.

• Porta San Marco 250 points

  The far south-west corner, downhill from everything, which means the reward here is the walk back. From outside, the arch frames the city like a picture nobody hung. The lane running up to it is one of the steepest bits of the whole level.

• Porta Tufi 250 points

  The southern tip of the level and its emptiest corner. The lanes thin out, the garden walls get longer, and then there is an arch with fields on the far side of it. The two hundred metres before a gate please me more than the gate.

Eating

Actual food.

Siena runs two kitchens. The sweet one started in the back rooms of the apothecaries, who held the spices, and a city order of 1772 forbade making panforte anywhere outside the walls. The savoury one came off the clay hills: dough rolled by hand, a belted pig fattened on acorns, sheep that graze on thyme. One kitchen was sold as medicine. The other was Tuesday.

Checked 5 September 2026.

Why here

Somebody stood here and decided.

Nobody chose a valley here. Siena sits on the high ground of the Tuscan upland, on the ridge that parts one river basin from the next, and the numbers say the rest: 320 metres at the town hall, 361 up at one end of the level and 288 down at the other. It grew over three hills, one at a time, and each hill got its own castle before anybody tied the three together with a single wall that follows the ground instead of a plan. That is why nothing in this level is flat and why its edge wanders. A city laid out along a watershed is a city where everything is either up or down. I have no legs and even I noticed.

Sources: www.treccani.it

Who ruled

Everyone who thought they owned this.

I outlasted all of them. It is the one thing I am good at.

678–1147

Officials, then counts, then bishops. Under the Lombards Siena was run by a gastaldo, and the oldest one anybody can name is Willerad, on record as alive in 678. The Franks arrived and the job turned into a county. Then from the tenth century the bishops began to matter more than the counts, who were pushed out into the countryside, and it was under the bishops' wing that the town first started running itself. Four hundred and seventy years, and not one of them was about anybody who lived here.

Sources: www.treccani.it

1147–1287

The commune. In 1147 a document names consuls for the first time, and the bishops are no longer in charge. By 1180 the emperor's chancellor had confirmed that Siena could mint its own coin, which settles the question of who runs a town more firmly than any speech. Then a podestà brought in from outside, the first of them a man from Lucca in 1199, and from 1202 a council summoned by a bell that did the work of a parliament. Called to government by ringing a bell. I would attend every session.

Sources: www.treccani.it

1287–1355

The Nine. Nine men, all of them from merchant and ordinary families rather than noble ones, held the government for sixty-eight years. Treccani calls it flatly the best government Siena ever had, and says what it spent the money on: the territory, and the buildings. Most of what you will walk past today was ordered by a committee of nine shopkeepers. And they signed the ground itself, which you will see when you get to the bottom of the hill.

Sources: www.treccani.it

1355–1557

Two hundred more years of the republic, spent almost entirely on rearranging its own committees. The pattern is the same each time: an emergency council is appointed, the emergency does not end, and the council stays. In 1454 they appointed one called the Balia and made it permanent and answerable to nobody, and it quietly ended up holding the actual power. The state's own archive draws the line at 1557: everything before that is filed as republican Siena. Two centuries of reshuffling and the filing clerks got the last word.

Sources: archiviodistatosiena.cultura.gov.it; www.treccani.it

1557–1860

Florence, from a distance. Prince Philip of Spain held the lordship of Siena and handed it on to Cosimo I in Florence, because he owed Cosimo a great deal of money. A city can change owner to settle an account. After that Siena kept its own councils and its own paperwork, but the man at the top was a governor standing in for somebody else's sovereign, first a Medici and later a Lorraine. Two hundred years in, in 1778, Pietro Leopoldo's laws finally got the fields and the trade moving again. The bill got paid eventually. It usually does.

Sources: www.treccani.it

1860–

Italy. In 1860 Tuscany was annexed to the Kingdom of Sardinia by a vote, Siena went along with the grand duchy it was part of, and shortly afterwards the whole arrangement was called Italy. That was the first time in eleven hundred years the question of who runs this place was answered by anybody who could see the hills from where they were sitting.

Sources: www.treccani.it; www.treccani.it

Three facts

Three things I know about this place.

1. The oldest secular building in Siena is not a sight. It is hiding. Its arches, spanning about 13 metres, were built into the church of S. Quirico on the crest of Castelvecchio and are still in there. What did survive out in the open is its name: the place was the stallum regis, the royal seat, where the Lombard official sat and the money came in, and the street it stood on is called Via di Stalloreggi to this day. Buildings get eaten. Street names are the last thing to go, and I say that with respect.

   Sources: www.treccani.it

2. There is a second set of lanes under the ones you are walking. Siena has more than 25 kilometres of tunnels cut into the rock beneath it, called the bottini after the barrel vault over them, a word first written down in 1226. They run 1.8 metres high and under a metre wide, which is a very good width, and until the pipes arrived in the early twentieth century they were the whole city's water. Nothing up here tells you they are down there. That is the sort of thing I would keep quiet about too.

   Sources: www.visitsiena.it

3. Siena is cut into seventeen contrade, and the city's own glossary calls them cities within the city. They are not districts on a map somewhere. They are lines on the ground, and the reason they are settled is that people argued about them for so long that in 1729 the governor, Beatrice Violante of Bavaria, published an order fixing every boundary, the number of them and how many people each one held. You will cross a dozen of those lines today, mostly without noticing, and the street signs will tell you which beast you are standing on. A city that spent centuries arguing about lines on the ground has my full attention. Lines on the ground are my entire diet.

   Sources: palio.comune.siena.it; palio.comune.siena.it

Counted from the streets in the level itself, not from a guidebook.

• 223streets
• 2,139dots
• 32.4km of street
• 40.5km on foot
• 11.5hours at a stroll