The rolling hills of Toscana offer landscapes that look like paintings, and a weekend in Val d'Orcia is the ultimate proof. Between cypress-lined drives, stone villages, and secluded abbeys, this corner of Toscana is best explored by car along the scenic SR2 Cassia and SP146 roads, as public transport is few and far between.
The best time to plan your trip is spring, between April and May, when the countryside turns a vivid green, or autumn, between October and November, to admire the warm colours of the foliage and soak up the harvest atmosphere, all while avoiding the summer heat and peak crowds.
The historic villages are closed to traffic, so you will explore strictly on foot after leaving your car in the blue-lined pay-and-display bays just outside the town walls. Every stop deserves unhurried time, wandering through historic centres and pausing to sample local specialities, such as handmade pici or a glass of Brunello.
2-day Val d'Orcia itinerary
Day 1 — From Pienza to thermal villages
Morning
Start your weekend in Pienza (Centro Storico), the Renaissance 'ideal city' commissioned by Pope Pius II and protected by UNESCO. Dedicate a couple of hours to the cathedral, the main square, and a walk along the town walls. When hunger strikes, stop for an informal lunch at La Bottega di Cacio along Corso Il Rossellino, perfect for filled rolls or a quick platter of local pecorino and cinta senese cured meats.
Afternoon
In the afternoon, head towards the small fortified hamlet of Monticchiello, known for its Teatro Povero folk theatre tradition. It is ideal for a relaxing stroll and offers lovely views over the cypress-lined winding roads. From there, drive towards San Quirico d'Orcia to visit the Horti Leonini, a pristine 16th-century Italian formal garden bordered with box hedges; entry is free and the visit takes about 45 minutes.
Evening
For the evening, move on to nearby Bagno Vignoni. Admire Bagno Vignoni e Piazza delle Sorgenti, where the central square is replaced by a vast Renaissance pool of warm sulphurous water. Dining here has a unique charm: Osteria del Leone, a historic 14th-century spot tucked just behind the thermal square, serves reimagined Tuscan dishes in an intimate setting. Booking well in advance is highly recommended.
Day 2 — Cypresses, abbeys, and Brunello
Morning
The day begins bright and early at dawn to photograph the Cappella della Madonna di Vitaleta, an iconic little chapel set between two rows of cypress trees between San Quirico d'Orcia and Pienza. Leave your car in the dedicated dirt parking area, followed by a walk of around 700-1000 metres. Immediately after, pull over along Via Cassia at Località I Triboli to see the famous Cipressi di San Quirico d'Orcia. If you enjoy walking, tackle the Sentiero Trekking Francigena: San Quirico d'Orcia - Bagno Vignoni, a scenic 5-6 km stretch through rolling hills and vineyards that takes around an hour and a half.
Afternoon
For lunch, Trattoria Osenna in San Quirico d'Orcia is a must for hand-rolled pici; book ahead. Afterwards, drive on to Montalcino to visit the Fortezza di Montalcino, a 14th-century fortress offering 360-degree views across the hills alongside an enoteca where you can taste Brunello (allow about an hour). Continue on to Castelnuovo dell'Abate for the Abbazia di Sant'Antimo, an isolated Romanesque abbey surrounded by ancient olive groves, famous for its Gregorian chants.
Evening
Heading back towards Pienza, wrap up your weekend with dinner at Sette di Vino in Piazza di Spagna, a relaxed osteria where the menu centres on platters of pecorino of various maturations, crostoni with lardo, and bruschetta.
Tips for planning your trip
- A car or motorbike is essential for getting around Val d'Orcia, as public transport runs infrequently. The villages are only about 10-20 minutes' drive from one another.
- Historic centres like Pienza, San Quirico, and Montalcino are pedestrianised zones closed to traffic: park in the blue-lined bays just outside the medieval walls.
- Bathing in the monumental pool in Bagno Vignoni's central square is strictly forbidden; to soak in thermal waters, head down to the streams in Parco dei Mulini or visit private spa facilities.
- To avoid disappointment, book restaurants and winery tastings a few days ahead, especially at weekends when tables fill up fast.
Where to stay
A historic 14th-century residence right in the spa village of Bagno Vignoni.
View on Booking →A scenic hotel located right against the walls of Pienza's historic centre.
View on Booking →A B&B and albergo diffuso set in the heart of Montalcino's historic centre.
View on Booking →