Three days in Siena: the city that lost to Florence and kept its Middle Ages
Two nights inside the walls, when the day coaches have gone and the shell-shaped square belongs to the people who live around it.
- Length
- 3 days, 2 nights
- Where you stay
- Siena
- Places
- 6 across 3 days
Siena spent two hundred years as Florence's equal and rival, then lost half its population to the Black Death in 1348, then lost the war, and never really grew again. That is the whole reason to come. A city that stops building stays the shape it was, and Siena is the best preserved medieval city centre in Italy.
It is also small, hilly and entirely brick. There is no straight street and no flat one. The centre sits on three ridges with valleys between them, so a five minute walk on a map is a climb, and the pleasure of two nights is that you stop hurrying and start using the shortcuts.
Most people come for four hours on a coach from Florence, see the square and the cathedral and leave. Staying is what the place is for: the square empties at six, the swifts come out over the rooftops, and the neighbourhood that owns the street you are standing in starts putting out trestle tables for dinner.
Highlights
- A cathedral striped like a humbug, with a marble floor most visitors never see uncovered
- The unfinished wall of the cathedral Siena was building when the plague arrived, now a staircase to the best view in Tuscany
- A fresco of good and bad government, painted in 1338 to remind the council what they were for
- The Campo at eight in the evening, when the day trippers have gone and everybody sits on the brick
Where to stay
Siena, two nights
A banking and wool city on the pilgrim road to Rome, rich enough by the thirteenth century to run a republic, fight Florence for two hundred years and commission the finest painting in Europe at the time. Then 1348 halved it, and the recovery never came.
The city is still divided into seventeen contrade, neighbourhoods with their own flags, fountains, museums, patron saints and church. People are baptised into one and stay in it. It is not a folk revival for visitors: it is the actual social structure of the place, and it is why the horse race in the square matters as much as it does.
Day by day
Day 1 in Siena
Arriving, San Domenico, and the Campo at dusk
The coach drops you at the top of the town near a huge, plain brick barn of a church that looks like a warehouse and holds the head of the patron saint of Italy in a gilded case. Catherine of Siena was a dyer's daughter who talked a pope into leaving Avignon; the chapel that keeps her relic is halfway down the right-hand wall and is worth the detour on the way to your room.
Then walk down to the square, which is the only place in Siena that is flat, and even it slopes. It is shaped like a shell, paved in brick, divided into nine segments for the nine men who governed the city when it was laid out, and everybody sits on it.
Do nothing else on the first evening. Get a table on the edge, or better, sit on the brick with an ice cream like everybody under thirty, and watch the light go off the tower.
- 16:00
Basilica Cateriniana San Domenico
ReligiousEnormous, bare and Gothic, built by preaching friars who wanted a room they could fill with a congregation rather than a work of art. Catherine's head and thumb are in the side chapel, which is either extraordinary or macabre depending on your background.
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- 18:00
Fonte Gaia
OtherThe fountain at the top of the square, fed by twenty-five kilometres of tunnels dug under the hills in the thirteenth century, which is how a city on a ridge with no river survived a siege. What you see is a copy; the eroded originals by Jacopo della Quercia are indoors in the old hospital.
- 20:00
Dinner in a contrada
EatWalk five minutes off the square in any direction and the prices drop and the customers change. Look for the flags: each neighbourhood has its own, and the restaurant under them is usually run by people from it.
With more time: The house Catherine grew up in is a few streets below, converted into a set of small chapels around the family dye works, and free. Just below it is the oldest of the city's covered fountains, still running, with three basins for drinking, washing and animals in that order.
Day 2 in Siena
The cathedral, the Maesta, and the hospital opposite
Everything today is on one small hilltop and takes the whole day anyway. The cathedral is striped inside and out in the black and white of the city's arms, which at first looks like decoration and quickly becomes disorientating: the columns bend the space and the whole nave seems to move.
Three things inside earn the ticket beyond the building itself. A pulpit carved by Nicola Pisano in the 1260s with seven panels of writhing figures. A library off the left aisle, frescoed floor to ceiling in colours that look wet. And the floor, if you are lucky enough to come when it is uncovered.
Across the square is the medieval hospital that took in pilgrims, the sick and abandoned children for eight hundred years, now four floors of museum. Its main ward is frescoed with scenes of hospital work rather than saints, which makes it one of the few places you can see ordinary medieval life painted by people who were living it.
- 09:30
Duomo di Siena
ReligiousGo at opening. The Piccolomini Library is through a door on the left and easy to walk past, and the marble floor panels around the high altar are uncovered even when the rest is boarded.
- 11:45
Museo dell'Opera del Duomo
CultureBuilt into the wall of the cathedral that was never finished. Duccio's Maesta is here, both sides of it, taken apart long ago: in 1311 the whole city walked it from the workshop to the altar with candles. Then climb the staircase inside the unfinished wall.
- 13:45
Lunch below the cathedral
EatThe lanes dropping away north of the square have small places doing pici and a glass of Chianti for very little. Sit down properly, because the afternoon is another museum.
- 15:00
Santa Maria della Scala
HistoricThe pilgrims' hospital, running from the twelfth century until the 1990s. The great ward is covered in fifteenth century frescoes of nurses, foundlings and doctors, and underneath the building are four more levels of chapels and tunnels going down into the hill.
With more time: The city's picture gallery, five minutes south, is where the Sienese painters are: Duccio, the Lorenzetti brothers, Simone Martini and a hundred gold-ground panels. It is quiet to the point of being empty and it is the best introduction to a school of painting that Florence eventually buried.
Day 3 in Siena
The town hall, the tower, and one last look
The last morning is the building at the bottom of the square, which has been the city hall for eight hundred years and is still exactly that. Upstairs is a room the governing council met in, painted in 1338 with a picture of what happens when a city is well governed and what happens when it is not.
It is the first large secular painting cycle in Europe and still the most useful. Good government is a busy street, a wedding, men threshing and a woman shopping. Bad government is a tyrant with fangs, and a field where the crops have failed and somebody is being robbed on the road. The councillors sat facing it while they voted.
If your knees are willing, the tower next to it is four hundred steps and gets you the roofs, the cathedral and the hills. Then lunch, and the coach back to Florence.
- 10:00
Palazzo Pubblico
ArchitectureThe civic museum is on the first floor and small, and the Lorenzetti frescoes are two rooms in. Look also for Simone Martini's mercenary captain riding across a landscape of camps and castles, painted in 1330 and among the earliest secular portraits in European painting.
- 12:15
Panforte and a coffee
EatThe spiced fruit cake keeps for weeks, travels well and is sold by weight in every bakery here. Buy a small one for later and eat something else now.
- 13:30
The coach back
TravelBuses to Florence go from the top of the hill roughly every half hour and take a little over an hour. Buy the ticket in the bar next to the stop rather than on board.
With more time: If you have an extra half day, San Gimignano is an hour away by bus with a change, and is the town with the towers. Go late in the afternoon when the coaches leave, not at noon when they arrive.
Before you go
Where to stay
Inside the walls, without exception. The whole point of Siena is the hours when the coaches are not there, and a hotel out on the ring road takes those away. The historic centre is small enough that anywhere within it is ten minutes from anywhere else, with a hill in between.
Rooms are relatively cheap for Tuscany outside the two Palio weeks, when prices multiply and everything is booked a year ahead. Bring shoes with grip: the streets are brick laid in a herringbone pattern and they are slippery in rain.
Getting there and around
Come by bus, not train. Siena's station sits down in the valley and connects badly, while the fast coaches from Florence run every half hour, take about an hour and a quarter, and drop you at the top of the hill a few minutes from the square. From Rome the train to Chiusi and a connection is the usual route.
Inside the walls it is all on foot and mostly uphill in whichever direction you are going. Cars are excluded from the centre, luggage over the cobbles is unpleasant, and there are escalators built into the hillside at two points that save a serious climb if you can find them.
Tickets, and the marble floor
A combined ticket covers the cathedral, its museum, the crypt and the baptistery, and is worth it as soon as you visit two of them. Nothing needs booking far ahead outside the Palio.
The cathedral floor is the thing to plan around: fifty-odd inlaid marble panels covering the whole nave, kept boarded over for most of the year to protect them and uncovered for a few weeks in late summer and autumn. If your dates fall in that window, the cathedral is a different building.
Eating
Sienese food is the plainest in Tuscany and unapologetic about it: thick hand-rolled pici pasta with breadcrumbs and garlic, bean soups, wild boar in winter, and a lot of pecorino from the hills south of here. The wine to drink is not the famous one from Montalcino unless you are spending; the everyday Chianti from the hills immediately outside the walls is what is on the table.
The city's sweet things are medieval and strange: a dense spiced fruit cake sold in flat discs, almond biscuits, and hard twice-baked biscuits meant to be dunked in sweet wine. Every bakery in the centre sells all three.
The thing that stays with people is not the cathedral. It is the scale: a whole city built before the Renaissance arrived and then left alone, where the tallest thing on the skyline is still a bell tower and the streets go where the ridges go.
Stay the second night. The square at ten in the evening is the reason.
Or make it a longer trip
These trips pass through here on the way somewhere else.
Make it your trip
Every stop, day and place here lands in your account as an editable trip. Move the days around, swap a city, add your own bookings and costs, and share it with whoever is coming.
Common questions
- Should I see Siena as a day trip from Florence?
- You can, and thousands do, and they get the worst version of it. The square and the cathedral are both busiest between eleven and four, which is exactly the window a day trip covers. Two nights costs very little more and gives you the mornings and the evenings, which is when Siena is unlike anywhere else.
- Can I see the Palio?
- The race runs on 2 July and 16 August, lasts about ninety seconds, and the centre of the square is free to stand in if you get there hours early and accept that you will not leave until it is over. Rooms with a window on the square cost a fortune and are booked a year ahead. The trial races in the days before are easier to watch and nearly as good.
- Is the cathedral floor worth planning dates around?
- If you care about this sort of thing, yes. It is uncovered for a stretch in late summer and early autumn and the dates are published each year. The rest of the time you see a handful of panels near the altar and boards over the rest.
- Siena or San Gimignano?
- Siena, easily, if you are choosing one. San Gimignano is a beautiful hour and a half and is overwhelmed by coaches for most of the day; Siena is a city you can live in for two days. If you have a car, do both and sleep in Siena.
- When should I come?
- May, June, September or October. July and August are hot and, around the Palio dates, unmanageable. Winter in Siena is cold, wet and almost empty, and the museums are yours alone, which some people would take over the weather.