Siena is a walled Gothic city of about 53,000 people, built along three ridges and closed to cars in the centre. Two days covers Piazza del Campo, the striped Duomo complex and the Lorenzetti frescoes in the Palazzo Pubblico. Come in spring or early autumn, or on 2 July or 16 August, when the Palio is run in the square.
Florence took the crowds and Siena kept the Middle Ages. The city stopped growing after the plague of 1348, so what it left behind is intact, brick and steep. The whole historic centre is UNESCO-listed, and almost none of it sits more than twenty minutes' walk from the Campo.
The square is a shell of brick paving divided into nine segments, one for each member of the Government of the Nine that ran Siena from 1287 to 1355. It slopes, so people sit on it. Come back after dark, when the Palazzo Pubblico is lit and the cafés along the curve have emptied.
Banded black and white inside and out, and floored with 56 inlaid marble panels that spend most of the year under protective boarding. They are uncovered for roughly ten weeks from late June and again from mid-August. The Piccolomini Library off the left aisle is included and should not be skipped.
Ambrogio Lorenzetti covered three walls of the Sala dei Nove with a working city, the countryside that feeds it, and opposite, the version where it all fails. It is the first great secular painting cycle in Europe, and it was propaganda aimed at the nine men who sat in that room.
Over 400 narrow steps to a bell chamber about 87 m up, with the Campo directly below and the Tuscan hills past the walls. Access is capped at 25 people at a time, so the wait at the foot of the stairs is usually longer than the climb itself.
One of Europe's oldest hospitals, working from the Middle Ages until the 1990s and now four floors of museum facing the cathedral. The Pellegrinaio ward is the reason to come: 15th-century frescoes by Domenico di Bartolo showing the hospital feeding, treating and raising the city's foundlings.
Painted for the cathedral's high altar and carried there in procession in 1311, then dismantled centuries later. The front panel and the Passion scenes from its back now hang facing one another, which is the only way anyone can see both sides of the same altarpiece.
Siena began a cathedral that would have swallowed the one it has, and the plague of 1348 ended the project. The finished wall still stands, and a staircase inside the museum puts you on top of it, in the one spot with the Duomo and the Torre del Mangia in a single frame.
A vast brick barn of a Dominican church on the Camporegio ridge, begun in the 13th century and stripped of almost all decoration. It keeps the head of St Catherine of Siena in a chapel frescoed by Sodoma. The terrace outside frames the Duomo across the valley.
Siena has no river, so medieval engineers cut roughly 25 km of tunnels through the sandstone to bring water up to the fountains. Volunteers from the Associazione La Diana take small groups into part of the Fonte Gaia and Fonte Nuova branches. Places go months ahead.
Cosimo I built the fortress in the 1560s to hold a city he had just conquered, and Siena turned it into a park. The ramparts are free, flat and open, and they look west over the walls. Enoteca Italiana reopened inside the bastions in 2025.
Gothic, quiet and rebuilt after a 17th-century fire, with Lorenzetti fragments in the transept.
Worth the walk east for Coppo di Marcovaldo's Madonna and the view back at the Duomo.
Etruscan tufa cellars, truffle from October, and one of the longest wine lists in Tuscany.
Trading since 1936 behind the Palazzo Pubblico: pici, tripe and no ceremony.
Opened in 1973 by a former Palio jockey, down an alley below San Domenico.
Open since 1840 and the oldest osteria in town: cold plates, jug wine, standing room.
A small shop with a tasting counter and a list built from growers rather than labels.
The deepest cellar of the five, and the one to book if you want to sit down.
North along Banchi di Sopra to the Fortezza, the station road and Porta Camollia.
The steep valley under San Domenico, the Goose contrada's ground, around a fountain first recorded in 1081.
Siena's park and its running track, and the ground the Wednesday market spreads across.
The terrace behind the Palazzo Pubblico, with the best of the everyday trattorie on it.
The SR222 north through Castellina and Radda. A car, and a driver who is not tasting.
Trading since 1879: cured Cinta Senese, pecorino, oil and boxed sweets.
A farmers' co-op since 1901, stocked from Tuscan producers rather than importers.
Siena's own saint. Solemn mass at San Domenico, then processions from her house in Fontebranda.
Concerts and masterclasses in courtyards and squares across the city, the Logge del Papa among them.
The cathedral's 56 marble panels come out from under their boards, in two windows either side of August.
Three bareback laps of the Campo, over in about ninety seconds, after four days of trials.
The Accademia Musicale Chigiana's summer season, in its own palace and in churches around town.
The patronal feast, on the eve of the second Palio, with the contrade processing to the Duomo.
The August race, dedicated to the Assumption. The city fills and the ropes close hours before the start.
A medieval market takes over the Campo for a weekend, with food, wine and craft stalls.
The nearest airport, about 79 km north. Tram to Firenze Santa Maria Novella, then the 131R bus or a train via Empoli.
About 119 km northwest and the main low-cost gateway. PisaMover to Pisa Centrale, then trains via Empoli.
The station sits in the valley below the walls, on the Empoli line. Most Florence services change at Empoli. Escalators climb toward Porta Camollia.
Autolinee Toscane runs Tuscany. The 131R from Florence takes about 75 minutes into Piazza Gramsci, which is also the departure point for the hill towns.
Hand-rolled flour and water pasta, thicker than spaghetti and never machine cut.
Bread, cavolo nero and beans, cooked once and reboiled the following day.
A dense cake of honey, candied fruit, nuts and spice, made here since the 13th century.
Chewy walnut and aniseed biscuits, sold by weight and meant for vin santo.
The Sienese sauce: tomato and aglione, a large mild garlic from the Val di Chiana.
Two ingredients, aged pecorino and black pepper, loosened with pasta water.
The native belted pig, DOP since 2012, eaten cured as salumi or grilled.
Soft almond biscuits, cracked on top and dusted white. IGP since 2010.
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