Tuscany is the most photographed region in Italy. Rolling hills dotted with cypress trees, isolated farmhouses, endless vineyards, medieval villages perched on every hilltop, this is the landscape Renaissance painters placed behind every portrait and what has represented Italy to the world for five centuries. It's not a tourist invention, the landscape is real, and UNESCO protects it as a World Heritage site in Val d'Orcia.
Inland Tuscany differs from the cities. Florence, Pisa and Lucca draw millions of visitors annually. But the countryside around Siena, Chianti, and Maremma remain accessible, less crowded, offering something cities cannot, the chance to stay put in a beautiful place, eat and drink well, walk through vineyards.
Siena
Siena is Italy's best preserved medieval city. The historic centre, built across three hills, has remained essentially unchanged since the 14th century, no modern buildings, no widened streets, no interruption of the medieval fabric. It became a UNESCO World Heritage site in 1995.
Piazza del Campo is Italy's finest medieval square. The shell of red bricks surrounded by Gothic palaces is unique in form and proportion. The Palio di Siena, the horse race between city districts held on July 2 and August 16, is Italy's most intense and controversial folk event, lasting ninety seconds but prepared all year, lived by the city with an emotional intensity no outside spectator fully comprehends.
Siena's Cathedral, with its black and white Gothic facade and marble inlay floor, ranks among Italy's greatest medieval artworks. The Opera Museum houses Duccio di Buoninsegna's Maestà, one of medieval painting's foundational pieces.
Val d'Orcia
Val d'Orcia, south of Siena, is quintessential Tuscan landscape. A UNESCO World Heritage site since 2004, it exemplifies how natural terrain was redesigned during the Renaissance to reflect the era's beauty ideals. Grey clay hills, cypress trees on every ridge, medieval villages emerging from farmland, this is the photograph of Tuscany.
Pienza is the Renaissance ideal city, built from scratch by Pope Pius II in the late 15th century to designs by Bernardo Rossellino. Palazzo Piccolomini, the Cathedral and Piazza Pio II form a unique Renaissance urban ensemble. Pienza is also celebrated for pecorino, sheep's milk cheese aged in the village cellars.
Montalcino is the home of Brunello, Tuscany's most celebrated red wine and among the world's most prized. The 14th century Angevin Fortress houses a wine bar where you taste local wines overlooking the countryside. Surrounding wineries welcome visitors.
San Quirico d'Orcia sits on the Via Francigena, the pilgrimage road connecting France to Rome. The 12th century Romanesque Collegiate Church and the Horti Leonini, a 16th century formal garden open to the public, are the main attractions.
Bagno Vignoni is a medieval village built around a thermal pool in the main square, where hot sulphur water replaces the pavement. It's one of Val d'Orcia's most unusual places.
Chianti
Chianti is the wine region between Florence and Siena, known worldwide for its red wine. Hills are covered with vineyards alternating with olive groves, oak woods and cypress. Villages are small, often just a castle with surrounding houses, and the road through them is the Chiantigiana, among Italy's most beautiful drives.
Greve in Chianti is the main Chianti Classico centre, with a triangular main square surrounded by arcades and wine shops and local product vendors. Saturday market attracts locals.
Radda in Chianti is one of the zone's most authentic villages, nearly intact medieval walls, a square with the Podestà's palace, positioned on a ridge with views across both sides of Chianti.
Monteriggioni is a medieval village on a hilltop with a perfectly preserved 14th century wall. The towers are the same ones Dante described in the Inferno. The interior is small but the external visual impact is exceptional.
San Gimignano
San Gimignano is the city of medieval towers, a UNESCO World Heritage site since 1990. In the Middle Ages it had seventy two towers, built by noble families as symbols of power. Fourteen remain, and the village silhouette with towers rising from countryside is one of Tuscany's most recognisable images.
The historic centre is walkable in a few hours. Piazza della Cisterna, with the medieval well at its centre and tower houses around it, is the village heart. Vernaccia di San Gimignano, a white DOCG wine, is served chilled in the centre's bars and wine shops.
San Gimignano gets very crowded in summer. Visiting early morning or late afternoon is far more pleasant.
Maremma and southern villages
Maremma is southern Tuscany, less touristy than areas around Siena and Florence. The villages of Pitigliano, Sorano and Sovana form so called 'Etruscan Tuscany', built on volcanic tuff ridges with Etruscan roads and rock tombs nearby. Pitigliano especially, with houses that seem to grow directly from the rock, is one of Italy's most spectacular villages.
Massa Marittima, in south Maremma, has a medieval Piazza Garibaldi considered among Tuscany's finest.
Practical information
Getting there. Florence is the main airport hub, with direct flights from many European cities. By train, the high speed line connects Florence with Rome in under ninety minutes. For the countryside you need a car, Val d'Orcia and Chianti villages lack adequate public transport.
When to visit. May and September are best, beautiful landscape (Val d'Orcia in May is green and flowering), fewer crowds, lower prices. September to October harvest season offers complete agritourism experience.
✓ Val d'Orcia, driving the Chiantigiana or SP146 between Pienza and San Quirico is worth the trip alone.
✓ Siena, stay in the city at least one night, the evening atmosphere after day trippers leave is completely different.
✓ San Gimignano, visit in early morning or late afternoon to avoid tour groups.
✓ Pitigliano, combine it with Sorano and Sovana, just kilometres apart, forming a complete Etruscan Tuscany itinerary.