Siena is Tuscany's great medieval rival to Florence — a city of steep brick lanes, Gothic palaces and a skyline still ruled by a single soaring tower. Where Florence perfected the Renaissance, Siena froze itself in the 13th and 14th centuries, and that suspended-in-time quality is exactly what makes it so rewarding to explore on foot after arriving by rail. The whole historic centre is a UNESCO World Heritage Site, built from the warm reddish-brown brick that gave its name to the colour "burnt sienna," and it remains fiercely proud of the seventeen contrade, or city wards, that still compete each summer in the Palio horse race.
Travellers joining the Orient Express La Dolce Vita can experience Siena as part of a wider journey through the Italian countryside, with the train's Tuscan routing bringing guests within easy reach of the city's rolling vineyards, cypress-lined roads and hilltop views before returning to the glamour of onboard dining and vintage carriages. It is a rare way to pair the romance of classic rail travel with one of Italy's best-preserved medieval cities.
Beyond its famous piazza, Siena rewards slow wandering — narrow stepped streets open suddenly onto panoramic views of the Tuscan hills, and nearly every corner reveals another chapel, tower or workshop that has changed little in centuries.
- ✦Piazza del Campo, one of Europe's finest medieval squares
- ✦Striped Gothic Siena Cathedral and its museum
- ✦Climb the Torre del Mangia for Tuscan hill views
- ✦Home of the historic Palio horse race
- ✦Rustic Tuscan cuisine: pici, ribollita and panforte
- ✦Seventeen storied contrade neighbourhoods
- ✦Gateway to Chianti and the Tuscan countryside via Orient Express La Dolce Vita
Places to See in Siena
Piazza del Campo
Siena's shell-shaped main square is one of Europe's greatest medieval plazas, ringed by palaces and sloping gently toward the Palazzo Pubblico. Twice a year it becomes the racetrack for the Palio di Siena, the city's storied bareback horse race.
Torre del Mangia
Rising above the Palazzo Pubblico, this slender 14th-century bell tower rewards the climb of some 400 steps with sweeping views across Siena's terracotta rooftops to the Tuscan countryside beyond.
Siena Cathedral (Duomo di Siena)
A masterpiece of Italian Gothic architecture, its striped black-and-white marble façade and bell tower are matched inside by an inlaid marble floor, Bernini and Michelangelo sculptures, and the frescoed Piccolomini Library.
Museo dell'Opera del Duomo
Housed alongside the cathedral, this museum preserves Duccio's monumental Maestà altarpiece and offers access to the Facciatone, the unfinished wall of an abandoned cathedral expansion with some of the best views in the city.
Palazzo Pubblico and Museo Civico
Siena's town hall since the 1300s, home to Ambrogio Lorenzetti's Allegory of Good and Bad Government frescoes — one of the most important secular fresco cycles to survive from the medieval period.
Basilica of San Domenico
A vast brick Gothic church associated with St. Catherine of Siena, holding her preserved head and thumb as relics and offering fine views back across the valley toward the Duomo.
Fonte Branda
One of Siena's oldest and best-preserved medieval fountains, tucked into the Fontebranda district near the sanctuary of St. Catherine's family home.
The Contrade neighbourhoods
Wandering between the city's seventeen historic contrade reveals flags, mascots and small museums devoted to each ward's identity and Palio history, offering a slice of Sienese life beyond the main sights.
Food & Gastronomy
Sienese cooking is rustic Tuscan food built on bread, beans, game and the region's celebrated olive oil and wine, and the city's pastry tradition is among the oldest in Italy.
- Pici — thick, hand-rolled eggless pasta, traditionally tossed with garlicky breadcrumbs (pici all'aglione) or a rich meat ragù.
- Ribollita — a hearty Tuscan bread and vegetable soup built around cannellini beans, cavolo nero and stale bread, twice-boiled for depth.
- Pappa al pomodoro — a thick tomato and bread soup finished with olive oil and fresh basil.
- Cinta Senese — a prized local heritage breed of pig, served as salumi or roasted, native to the Sienese hills.
- Panforte — Siena's iconic dense, spiced fruit-and-nut cake, dating back to the medieval period and traditionally eaten at Christmas.
- Ricciarelli — soft, chewy almond biscuits dusted with powdered sugar, another centuries-old Sienese speciality.
- Cantuccini and Vin Santo — crunchy almond biscotti dipped in Tuscany's sweet amber dessert wine.
- Pecorino Toscano and Chianti — the surrounding countryside supplies excellent sheep's-milk pecorino and some of Italy's finest reds, from Chianti Classico to Brunello di Montalcino nearby.
Piazza del Campo and its side streets are lined with trattorie serving these dishes, while the Wednesday market near La Lizza is the best place to see local produce, cheeses and cured meats up close.
