Day-by-day programme of this 3-day itinerary across Tuscany.
Day 1 โ Chianti Classico
Set off early: by mid-morning you reach Chianti, the hilly area between Florence and Siena, the green heart of Tuscany made of vineyards, olive groves, oak woods and stone villages. It's a full day: if you prefer a slower pace, pick two villages and spend the rest of the time at the wineries. The road to follow is the scenic Chiantigiana (SR222).
- ๐ Montefioralle โ A tiny elliptical fortified hamlet perched above Greve, one of the loveliest in Italy: a single ring of cobbled lanes wrapped around the church of Santo Stefano, with stone houses, archways and vines climbing the faรงades. You can walk it in minutes, but the view over the Chianti vineyards stays with you. Then you head down on foot to Greve, the town at its feet.
- ๐ Greve in Chianti โ The gateway to Chianti, with its theatrical triangular Piazza Matteotti, ringed by irregular arcades, wine shops and food stores. It's the best place to soak up the atmosphere of Chianti Classico, marked by the famous Black Rooster, and for a first tasting in one of the historic wine bars on the square. On Saturday mornings there's a market. From here you follow the scenic Chiantigiana road towards Radda.
- ๐ Radda in Chianti โ One of the three historic villages of Chianti, grown around the 14th-century church of San Niccolรฒ and the imposing Palazzo del Podestร , its faรงades dotted with coats of arms. You stroll along the medieval walkway that circles the centre, with glimpses of vineyards, and it's a good spot for a light lunch of cured meats and Chianti. Then you head down to Gaiole, among castles and historic farms.
- ๐ Gaiole in Chianti โ An old market village of Sienese Chianti, today an ideal base to explore wine castles and estates. A few kilometres away rises Castello di Brolio, fief of the Ricasoli family, where in the mid-1800s the "iron baron" perfected the recipe for Chianti wine. Just nearby, among the vineyards, the Castello di Meleto is only a few minutes away.
- ๐ Castello di Meleto โ A medieval castle set among the vineyards a few minutes from Gaiole, with two cylindrical towers and, inside, an elegant little 18th-century theatre. Today it is a winery: you can tour the historic halls and the cellars carved into the rock, with a tasting of Chianti Classico and vin santo overlooking the hills. After the visit you head to Castellina, the last village of the day.
- ๐ Castellina in Chianti โ A village of Etruscan origin perched between the Arbia, Pesa and Elsa valleys, dominated by its fortress. Its hidden heart is the Via delle Volte, an evocative covered medieval walkway carved into the walls, today dotted with shops and wine bars. Inside the castle, the small Archaeological Museum of Chianti tells the story of the local Etruscans. At sunset you head to your farm stay for dinner and rest.
- ๐จ Hotel Belvedere di San Leonino
Day 2 โ Val d'Orcia: Vino Nobile and the Renaissance
From Chianti you head south into the Val d'Orcia: a wide UNESCO-listed countryside of clay hills, neat rows of cypress trees, white gravel roads and medieval villages on the heights. This is postcard Tuscany. Today the great Vino Nobile of Montepulciano, the Renaissance perfection of Pienza with its pecorino cheese, the iconic views of Vitaleta and, to close, the thermal square of Bagno Vignoni.
- ๐ Castelnuovo Berardenga โ The last edge of Sienese Chianti and a natural gateway to the Val d'Orcia: a quiet village looking over the countryside, with its 19th-century villa and Italian garden. A short morning stop for a coffee before the landscape opens onto the clay hills. From here you head south, towards the ridge of Montepulciano.
- ๐ Montepulciano โ An elegant Renaissance village perched on a ridge, on the border between Val d'Orcia and Val di Chiana, famous for Vino Nobile di Montepulciano. The main street climbs steeply past noble palaces to the theatrical Piazza Grande, a perfect panoramic balcony. Many historic cellars carved into the tufa beneath the centre offer tours and tastings of the Nobile. Then you drive down through the clay hills towards Pienza.
- ๐ Pienza โ The Renaissance "ideal city", commissioned by Pope Pius II, who transformed his birthplace into a harmonious jewel: Piazza Pio II, the Cathedral and Palazzo Piccolomini are a UNESCO site. It's also the capital of Pienza pecorino, to be tasted in the shops along Corso il Rossellino, perhaps paired with a glass of red. A walk along the alleys with romantic names (Via dell'Amore, Via del Bacio) offers views over the hills. Then you drive down to the most photographed cypress lane in Tuscany.
- ๐ Chapel of the Madonna di Vitaleta โ A tiny white church framed between two rows of cypress trees on a wheat-covered hill: it is perhaps the most iconic image of the entire Val d'Orcia. You reach it on foot from a gravel road linking San Quirico d'Orcia to Pienza; you can't go inside, but the view, especially in the golden light of late afternoon, is well worth the short walk. This is the moment for photographs. Then it's just a few minutes' drive to the village of San Quirico.
- ๐ San Quirico d'Orcia โ A medieval village along the ancient Via Francigena, compact and authentic: you visit the lovely Romanesque Collegiate church of Saints Quirico and Giulitta, with its carved portals, and the Horti Leonini, a refined 16th-century Italian garden. All around, the landscape is pure postcard, made of hills, gravel roads and cypress trees. A few minutes away, the water-square of Bagno Vignoni closes the day.
- ๐ Bagno Vignoni โ One of the most unusual villages in Italy: in place of the main square there is a large 16th-century pool brimming with steaming thermal water, the Piazza delle Sorgenti, used since Roman times and frequented by Saint Catherine and Lorenzo the Magnificent. You can't bathe in the pool itself, but just below the village the free pools of the Parco dei Mulini offer warm water for free, overlooking the Orcia river. As evening falls you head back to the farm stay for the night.
- ๐จ Agriturismo Le Casaline - Val d'Orcia
Day 3 โ Brunello, abbeys and hot springs
Last day, heading west and then home: the Brunello of Montalcino from its Fortress, the Romanesque purity of Sant'Antimo Abbey, the view from Castiglione d'Orcia and a grand finale of pure relaxation in the free hot springs of Bagni San Filippo, before getting back on the A1 motorway home. Bring a swimsuit, a towel and water shoes for the springs.
- ๐ Montalcino โ A town of Etruscan origin perched on the last hills that slope down towards the Maremma, surrounded by woods and vineyards. The town is dominated by the mighty 14th-century Fortress, whose ramparts offer views from Siena all the way to Monte Amiata. This is the home of Brunello, one of the most famous and long-lived red wines in the world: to taste it, simply stay inside the Fortress, where the wine shop is. Below the town, among the vineyards, Sant'Antimo Abbey awaits.
- ๐ Sant'Antimo Abbey โ Set in a hollow of olive and cypress trees near the hamlet of Castelnuovo dell'Abate, it is one of the purest Romanesque abbeys in Italy, built between the 8th and 12th centuries. The pale stone of the exterior and the light filtering into the three-nave interior create a suspended, crowd-free atmosphere; legend even traces it back to Charlemagne. Then you climb up to the terrace-village of Castiglione d'Orcia.
- ๐ Castiglione d'Orcia โ A small perched village that acts as a natural terrace over the whole valley, from the slopes of Monte Amiata to, on clear days, the sea. The heart of the village is the intimate, stone-paved Piazza Il Vecchietta, named after the painter born here in the 15th century; higher up, the ruins of the Rocca Aldobrandesca offer the best view and it's the right spot for a lunch with a panorama. From here you head down to one of the most famous thermal basins in Tuscany.
- ๐ฏ Fosso Bianco, Bagni San Filippo โ The grand finale of the weekend: a path through the woods leads down to the Fosso Bianco, where sulphurous thermal waters create little waterfalls and natural pools of warm water you can soak in for free. The scene is dominated by the "Balena Bianca" (White Whale), a spectacular white limestone formation resembling a whale's back. Entry is free (you only pay for parking): all you need is a swimsuit, a towel and water shoes. Refreshed, you get back on the A1 motorway home, with soft skin and your eyes full of Tuscany.
