Start from 33 curated places around Siena, IT, then choose the recommendations that fit your guests.
Restaurants & cafés
Osteria Permalico
A small, contemporary osteria on a quiet lane near Piazza del Campo that draws a strongly local crowd with honest Sienese cooking at prices that don't punish the postcode. Pici all'aglione and hand-rolled pasta with cinghiale ragù are the anchors; the room is compact with mismatched wooden furniture and the service moves without fuss. Reservations are recommended for dinner.
La Taverna di San Giuseppe
A long-established Sienese trattoria in vaulted Etruscan cellars on Via Giovanni Dupré, known for truffle-dressed pastas, Florentine steak, and a wine cellar that runs deep in both sense and depth. The stone-and-brick rooms seat around 80 and manage to feel intimate. Widely regarded as one of the most consistently reliable full-service restaurants in the city.
Trails & outdoors
Via Francigena Segment 94: Siena to Ponte d'Arbia
The southbound leg of the medieval pilgrim road leaving Siena passes through the edge of the Crete Senesi landscape — clay hills, isolated farmhouses, and long views across Val d'Arbia with no motorway noise. The trail follows white unpaved roads through terrain that looks genuinely unchanged, passing the fortified Grancia di Cuna granary about halfway. The full segment runs 25km; most walkers do the first 10–12km and turn back or arrange a shuttle.
Crete Senesi Loop via Asciano
The Crete Senesi south of Siena are a landscape unlike anything else in Tuscany — eroded clay hillsides called biancane form rounded, pale-grey slopes that look lunar or Saharan depending on the light. The loop from Asciano (accessible by train from Siena) follows ridge roads with long views, passing isolated agriturismo estates and the Basilica di Sant'Agata before returning through Sienese countryside. Best in spring when the wheat is green, or autumn when the grain stubble and morning fog combine.
Things to do
Museo dell'Opera Metropolitana
The cathedral museum beside the Duomo holds Duccio di Buoninsegna's Maestà — the two-sided altarpiece painted between 1308 and 1311 that defined Sienese painting for the following century. The front face shows the Virgin enthroned with saints; the reverse contains 40-plus narrative panels depicting the life of Christ. A temperature-controlled room on the first floor holds the work at eye level, giving closer access than most comparable masterpieces in Italian museums. The museum also offers a terrace view over the Duomo facade and the city.
Pinacoteca Nazionale di Siena
The national gallery occupies a medieval palazzo on Via San Pietro and holds the most comprehensive collection of Sienese Gothic and early Renaissance painting anywhere — Duccio, Simone Martini, the Lorenzetti brothers, Sassetta, Beccafumi — arranged chronologically so you can track the Sienese school from its 13th-century origins through the 17th century. The museum is consistently less crowded than its peers in Florence, and has seating throughout, making it well-suited to a longer visit.
Landmarks & sights
Piazza del Campo
The shell-shaped central piazza is the civic heart of Siena and one of the great medieval public spaces in Europe — nine wedge-shaped segments of brick slope gently toward the Palazzo Pubblico, designed to converge all eyes on the seat of government. The piazza reads differently at each hour: morning quiet, noon sun bouncing off warm terracotta, and evening when Sienese families claim the edges. The Palio horse race runs here twice a year, and the weeks before each race the whole city reorganizes around it.
Cattedrale di Santa Maria Assunta
Siena's cathedral is one of the most elaborately decorated Gothic buildings in Italy — the black-and-white striped marble exterior sets expectations, but the interior overwhelms them, with an inlaid marble floor of 56 panels (largely covered except in September–October), Nicola Pisano's pulpit, and the small Piccolomini Library frescoed by Pinturicchio. Plan more time than you think you need: most first-time visitors underestimate how much is crammed into the space.