How to Plan the Perfect Week in Southern Tuscany

Southern Tuscany — the area south of Siena encompassing the Val d'Orcia, the Crete Senesi, Montepulciano, Pienza and Montalcino — is the most concentrated collection of natural beauty, gastronomic excellence and cultural richness in Italy. Planning a week here well makes the difference between a good holiday and a life-changing one.

Where to Base Yourself

Montepulciano is the best base for a southern Tuscan week: it sits at the intersection of all the key destinations, has excellent accommodation options from agriturismi to boutique hotels, and is the home of Vino Nobile — the wine that will accompany most of your meals. Distance to key destinations: Pienza 14km, Montalcino 40km, Siena 65km, Chianciano Terme 10km.

The 7-Day Itinerary

Day 1 — Arrival and Montepulciano Arrive at Montepulciano (from Florence: 1h30; from Rome: 2h30). Settle in, walk the corso to Piazza Grande at sunset. Evening: the Eramo Sunset Wine Tasting — the perfect introduction to the territory through its wines.

Day 2 — San Biagio + Pienza Morning walk to San Biagio. Drive to Pienza for lunch (pecorino, salumi, local bread). Afternoon: Palazzo Piccolomini and the Val d'Orcia viewpoints. Return to Montepulciano for dinner.

Day 3 — Montalcino + Brunello Drive to Montalcino (40km, 45 min). Visit the medieval fortress. Tasting at one of the Brunello estates (Poggio Antico, Il Poggione or Ciacci Piccolomini — book in advance). Return via the Via Francigena road for extraordinary views.

Day 4 — Val d'Orcia + Bagno Vignoni A slow day: drive the Val d'Orcia without a destination. Stop at Castiglione d'Orcia, the Orcia river valley viewpoints and Bagno Vignoni for the thermal piazza. Picnic lunch with local produce.

Day 5 — Crete Senesi + Asciano Drive north into the Crete Senesi — the lunar, clay-sculpted landscape between Siena and Asciano. Visit the Abbazia di Monte Oliveto Maggiore (extraordinary frescoes by Sodoma and Signorelli, free entry). The most dramatic and least-visited landscape in Tuscany.

Day 6 — Cooking Class + Montepulciano Morning: Pasta Fresca & Vino class at Eramo — make pasta by hand, then eat it for lunch with Vino Nobile. Afternoon: rest. Evening: final dinner in Montepulciano — try the Rosso di Montepulciano as an aperitivo wine.

Day 7 — Siena and Departure Drive to Siena (65km, 1 hour). Piazza del Campo, the Duomo (book the Porta del Cielo visit in advance for the rooftop), the Pinacoteca Nazionale. Lunch in Siena, then departure.

Essential Bookings

• Eramo Sunset Wine Tasting — book at least 2 weeks in advance in peak season
• Pasta Fresca & Vino class — book at least 48 hours in advance
• Brunello cantina visit — book directly with the estate, 1 week in advance
• Siena Duomo Porta del Cielo — book online at operaduomo.siena.it