Siena in 2 days, on foot

This 2-day self-guided walking plan for Siena covers 20 narrated sights in an easy day-by-day order. Each day is split into a morning and an afternoon loop, and every stop has a two to three minute audio story in the Gingerguide app.

You set the pace: this is a suggested order, not a schedule. Walk it in 2 days, or stretch it out. Reorder freely; Siena rewards a detour.

Day 1

Morning

1. Piazza del Campo: UNESCO-listed Piazza del Campo is one of Europe's greatest medieval squares, a shell-shaped brick piazza divided into nine sections representing Siena's Council of Nine, sloping gently toward the magnificent Gothic Palazzo Pubblico.
2. Palio di Siena: Held on 2 July and 16 August since 1633, the Palio is a bareback horse race around Piazza del Campo in which ten of Siena's seventeen contrade (city districts) compete, a ninety-second race that embodies seven centuries of civic identity, rivalry, and passion.
3. Torre del Mangia: Soaring nearly 88 metres above the Piazza del Campo, the Torre del Mangia (1338–1348) is one of the tallest medieval secular towers in Italy, its 503 steps lead to a panoramic summit commanding all of Siena and the Tuscan hills beyond.
4. Palazzo Pubblico & Civic Museum: Siena's Gothic town hall (begun 1297) houses the Civic Museum containing Simone Martini's sublime Maestà (1315) and Ambrogio Lorenzetti's Allegory of Good and Bad Government (1338–39), perhaps the most important secular fresco cycle in medieval European art.
5. Siena Cathedral (Duomo): A masterpiece of Italian Gothic-Romanesque architecture, Siena Cathedral is famous for its alternating black and white marble stripes, Nicola Pisano's sculpted pulpit (1265-68), and its extraordinary floor of 56 inlaid marble panels depicting scenes from history and myth.

Afternoon

1. Piccolomini Library: Accessed from the Cathedral's left nave, the Piccolomini Library (1502–07) contains ten brilliantly preserved frescoes by Pinturicchio depicting the life of Pope Pius II, among the finest examples of Renaissance fresco painting in Tuscany.
2. Baptistery of San Giovanni: Below the Cathedral apse, the Baptistery of San Giovanni (begun 1316) houses an extraordinary baptismal font, a collaborative masterpiece by Jacopo della Quercia, Lorenzo Ghiberti, and Donatello, representing the highest achievement of early 15th-century Italian sculpture.
3. Santa Maria della Scala: One of Europe's oldest hospitals, operating from the 9th century until 1995, now a vast museum complex, its Pilgrim Hall (Sala del Pellegrinaio) contains remarkable 15th-century frescoes depicting hospital life with extraordinary documentary realism.
4. Pinacoteca Nazionale: The National Picture Gallery in Palazzo Buonsignori houses the world's most complete collection of the Sienese school, Duccio di Buoninsegna, Simone Martini, the Lorenzetti brothers, tracing the development of one of medieval Europe's greatest artistic traditions.
5. Contrade of Siena: Siena's 17 contrade (city districts), each with its own church, museum, fountain, symbol, and fierce civic identity, form a living medieval social structure in which every Sienese citizen is baptized at birth and belongs for life.

Day 2

Morning

1. Museo dell'Opera del Duomo: Housed in the unfinished nave of the never-completed great Cathedral expansion, the Opera del Duomo museum safeguards Duccio's monumental Maestà (1308–11), one of the defining works of Italian medieval painting, along with sculptures by Giovanni Pisano.
2. Via di Città & Banchi di Sopra: The great curved spine of Siena's historic centre, Via di Città and Banchi di Sopra form the main corso of the medieval city, lined with Gothic and Renaissance palaces including the Palazzo Chigi-Saracini and linking Piazza del Campo to the northern terzo.
3. Basilica di San Domenico: The great Gothic brick basilica of the Dominicans in Siena (begun 1226) is the spiritual home of St Catherine of Siena, housing her head (as a relic) in the Cappella di Santa Caterina, along with Sodoma's finest paintings and a chapel containing her cell.
4. Fontebranda: The Fontebranda (c.1246) is Siena's largest and most historic public fountain, a magnificent Gothic structure of three brick arches reflected in a pool below, mentioned by Dante in the Inferno and the neighbourhood fountain of St Catherine of Siena.
5. Piazza Salimbeni: Piazza Salimbeni is one of the most perfectly preserved medieval piazzas in Italy, three palaces from three different centuries (Gothic, Renaissance, Mannerist) enclosing a harmonious square that has been the headquarters of the Monte dei Paschi di Siena bank since 1472.

Afternoon

1. Oratorio di San Bernardino: Adjacent to the Basilica di San Francesco, the small two-story Oratorio di San Bernardino contains one of the finest concentrations of early 16th-century Sienese fresco painting, works by Sodoma, Beccafumi, and Girolamo del Pacchia in an intimate chapel space.
2. Fortezza Medicea & Enoteca Italiana: The Fortezza Medicea is the imposing 16th-century Medici fortress at the northern edge of Siena, now transformed into a public park and home to the Enoteca Italiana, a permanent wine exhibition and tasting venue showcasing bottles from across Italy.
3. Via Francigena through Siena: Siena was a major staging post on the Via Francigena, the great medieval pilgrim route from Canterbury to Rome, and the city's history, hospitals, and urban form were shaped by the hundreds of thousands of pilgrims who passed through its gates every century.
4. Sienese Cuisine & Traditions: Siena's culinary traditions reflect its medieval mercantile culture and Tuscan agricultural heritage, from the iconic panforte (spiced fruit-and-nut cake) and ricciarelli (almond cookies) to pici pasta, wild boar, pecorino cheese, and the wines of the surrounding countryside.
5. Sienese Gothic Architecture & Medieval Skyline: Siena's historic centre is a perfectly preserved medieval city of red brick, Gothic palaces, private towers, and terracotta rooftops, a UNESCO World Heritage Site whose skyline has barely changed since the 14th century and represents one of the finest surviving examples of medieval Italian urban design.

Full Siena guide and all stops →