Siena discovery guide

Siena's entire historic centre is a UNESCO World Heritage Site, inscribed in 1995 under criterion (i) among others. Its cathedral holds sculpture by Nicola and Giovanni Pisano, Donatello, Michelangelo and Bernini in one building, and Piazza del Campo is the finest medieval square in Europe.

The main travel issue

It is a day-trip from Florence for most people, and a day trip is the wrong shape for it. The coaches arrive mid-morning and leave by five, the city is steep, and the two days that matter most — the Palio on 2 July and 16 August — make the centre impossible unless you planned for them a year out.

The solution

Stay a night. Siena empties in the evening and the square at dusk is the thing people remember. Avoid the Palio dates unless you are coming for them; the days around the trial races are busier than the race itself and the cathedral cuts its hours. Come in May or October.

The short answer

May and late September to October are the best months, and the two dates to actively decide about are 2 July and 16 August, when the Palio runs.

Spring

April to June is excellent: warm, the hills green before the summer burns them, and the city busy without being overwhelmed. May is the single best month in Siena. From April to October the cathedral also runs the Clavigero, its ceremonial 7:15 am opening, which is the quietest way anyone will ever see that building.

Summer

July and August are hot, crowded and dominated by the Palio. The races themselves are on 2 July and 16 August, and the days immediately before each carry six trial races and the contrada dinners — so the first week of July and the middle of August are the busiest and most expensive of the year. The cathedral cuts its hours to 10:00–18:00 from 22 to 24 June and from 5 to 13 August. If the Palio is not the point of the trip, avoid those windows.

Autumn

Late September and October are the other good window, and arguably better than spring: the light in the Crete Senesi after the harvest is the thing photographers come for, the crowd has gone, and the food turns to game and new oil.

Winter

Cold on a hill at 322 metres, often grey, and very quiet. January averages 6.4°C. The cathedral complex runs reduced hours — 10:30 to 17:30 from January to March, with the cathedral itself opening only at 13:30 on Sundays and holidays. In exchange you get a medieval city almost to yourself, which is a real trade.

The one rule

Check the Palio dates before booking anything. They do not move: 2 July and 16 August, every year.

A day, which is what most people give it

Arrive early rather than with the coaches. Start in Piazza del Campo and climb the Torre del Mangia for the view that explains the city's shape. Then the Duomo complex — cathedral, Piccolomini Library, baptistery and museum, which share one ticket — and Santa Maria della Scala, the medieval hospital opposite, if there is time.

Two days, which is the right amount

The second day is for the city rather than the monuments. Walk the three terzi the centre divides into, find the contrada churches, fountains and museums in the streets above the square, and go into the Pinacoteca Nazionale for the Sienese painters the rest of the world under-rates. Then do nothing in particular on the Campo in the evening, which is what the square is for.

Using Siena as a base

Siena is the natural base for southern Tuscany in a way Florence is not. The Crete Senesi begin immediately south-east, Montalcino and the Val d'Orcia are within an hour, San Gimignano and Volterra are west, and Chianti starts on the city's northern doorstep. A car helps here more than anywhere else in this rollout.

If you are coming for the Palio

Decide a year ahead. The race is on 2 July or 16 August, lasts under ninety seconds, and the four days before each one carry six trial races plus the contrada dinners. The centre of the square is free to stand in but fills hours beforehand and cannot be left once full; seats and windows are private property. Children may no longer stand in the centre at all and must watch from a stand or a window.

What to skip

Do not try to add Siena to a day that already contains San Gimignano and a vineyard. It is a steep city that rewards slowness, and the version of it you get in ninety minutes is a photograph of a square.

The contrade, which are the actual subject

Siena is organised into seventeen contrade — neighbourhood communities with their own names, colours, animals, churches, fountains, museums, officials and rivalries. They are not a heritage project or a Palio administrative device. A Sienese is baptised into a contrada, eats at its dinners, marries within or across its alliances, and inherits its grudges; membership is the primary civic identity in the city and it operates all year, not twice a year.

Understanding this changes what a visitor is looking at. The flags on a street are a territorial statement. The fountain with an animal on it is a contrada's baptismal font. And the Palio is the contrade's event, which is why it would run exactly as it does if no visitor ever came.

A city that stopped

Siena held 50,000 people before the Black Death of 1348 and holds about 53,000 now. The plague, then the long war with Florence, then the end of the republic in 1555, removed the city's capacity to grow — and a city that does not grow does not demolish. The medieval centre survives because nothing replaced it, and the Sienese are entirely aware that their greatest asset is the consequence of their greatest defeat.

Sienese painting

Siena produced a school of painting that went a different way from Florence's: flatter, more golden, more Byzantine in descent, less interested in perspective and anatomy than in pattern and devotion. Because Florence won the argument about what Italian art was for, Sienese painting is systematically under-weighted outside Italy. The Pinacoteca Nazionale and the cathedral museum are where to correct that.

Food and the land

The cooking is inland Tuscan and poor by design — pici, the hand-rolled pasta, ribollita, pecorino from Pienza, wild boar. Panforte and ricciarelli are the city's own medieval confections and still sold everywhere. The wine is the single most famous product of the surrounding hills: Chianti to the north, Brunello to the south.

The cathedral as an argument

The Duomo is a statement about Siena's ambition rather than merely a church. The unfinished nave beside it — the Facciatone, a wall and an aisle standing in open air — was meant to make this the largest cathedral in Christendom, and the project died with the Black Death. Climbing it gives the best view in the city and a very direct lesson in what 1348 cost.

A city of 53,000 taking several million visitors

Siena's pressure is structural rather than seasonal. The historic centre is medieval, which means narrow, steep and finite, and it absorbs a day-trip flow from Florence that arrives and departs within a few hours. The city is not large enough to disperse that, so where and when a visitor spends matters more here than in a big city.

Practical ways to travel well here

• Stay overnight if you possibly can. This is the single most useful thing a visitor can do for Siena. A day-tripper contributes the crowding in the hours the centre is tightest and almost nothing to the city's economy; after about six in the evening Siena belongs to Siena again, and that is also when it is best.
• Respect the Palio as an event that is not for you. The contrade run it for themselves. If you are in the city for it, stay out of the way of the processions, do not wear another contrada's colours into its streets, and understand that the race is a civic matter rather than entertainment.
• Treat the cathedral as a working church. Mass is said on weekdays at 9:30 in the Madonna del Voto chapel and several times on holidays, and visitor hours are built around that. Covered shoulders and knees are expected.
• Walk uphill away from the square. The streets above Piazza del Campo — towards Provenzano, San Francesco, the contrada churches and fountains — carry a fraction of the people and are where the city actually lives.
• Buy the combined pass rather than one monument. The Opera della Metropolitana funds the cathedral complex's conservation from admissions, and the ticket includes a free audioguide.

What Siena actually costs

Siena is expensive for its size, because a city of 53,000 with a World Heritage centre has limited rooms and very high demand. It is cheaper than Florence or Venice but dearer than Pisa or Bologna, and the cost is concentrated almost entirely in accommodation.

The two dates that change everything

Room rates around the Palio — the first days of July and the middle of August — are in a different category from the rest of the year, and availability runs out many months ahead rather than weeks. This is not peak-season pricing; it is a different market. The weeks either side are ordinary.

The monuments

The Opera della Metropolitana runs the cathedral, the Piccolomini Library, the baptistery, the crypt and the museum on a combined pass, and the ticket includes a free audioguide on your own phone. Prices are published by the operator rather than quoted here. Two things are worth knowing: the complex is genuinely large enough to justify a full pass rather than a single entry, and climbing the Facciatone of the unfinished nave is part of it.

Where the money goes

• Accommodation is the whole budget question. Staying inside the walls costs more and is worth it, because the city after six is the reason to be here.
• Eating is good value away from Piazza del Campo and poor value on it. The square charges for the view, which is a fair trade once.
• Watching the Palio from the centre of the square is free. The seats, balconies and windows around it are private property and priced accordingly; there is no official central box office for them.
• A car is the one transport cost worth paying here, because Siena is the base for southern Tuscany and the Crete Senesi and Val d'Orcia are not well served by public transport. Park outside the walls, not inside.