Unforgettable Holidays in and around a medieval hilltop village in Southern Tuscany
Turn your dreams into the reality of a truly memorable Tuscan getaway.

Around Montisi

If you have a little time to spare here are some villages within a half hour drive of Montisi which you may like to visit:

Petroio (10km south east)


Petroio is a delightful medieval village perched on a hill, 10km south east of Montisi. Viewed from above (and I took the photograph from a hot air balloon) you can see that the streets are wrapped in a spiral. The village was built entirely of sandstone and it is well worth the short walk from the car park at the bottom of the hill up the extremely narrow streets to the top. There is also a very interesting terracotta museum in a 13th century building which has been restored and merits a visit .

San Giovanni d’Asso (6km west)

Montisi is part of the commune of San Giovanni d’Asso and the local council offices are housed in the rather magnificent 12th century castle in the centre of the village, which can be seen from some distance along the road from Montisi. Despite being a tiny place it is internationally renowned for its truffle festival which takes place over the 2nd and 3rd weekends in November each year and was even featured in Conde Nast traveller in an article about truffle hunting. The truffle museum in the basement of the castle is worth a visit.

San Quirico d’Orcia (20km south)

The beautiful small walled town of San Quirico D’Orciam is often overlooked by visitors to nearby Pienza and Montepulciano and is therefore usually very quiet! Dating back to Etruscan times, there are paved streets to wander taking you past colourful gardens and plenty of places where you will be tempted to stop and have something to eat and drink. And unlike many of the towns in this part of Tuscany it’s not on a hill so there are no steep streets or steps to climb.

Castelmuzio (3km south)

Castelmuzio is just across the valley from Montisi and makes a lovely walk if you don’t mind the hilly terrain. It’s a tiny but beautifully preserved village which dates back to Etruscan times and has three churches! There is a very friendly coffee bar and restaurant in the middle of the village inside the 15th century tower.

Pienza (13km south)


Pienza is an artist’s and photographer’s dream – and no visit to this area is complete without a wander down its cobbled main street with mouth-watering smells of salami and pecorino cheeses wafting around you. In 1459, Pope Pius 11, who was born in Pienza, decided to turn it into the ideal Italian city and, although he died before his dream was fully realised, he left a beautiful Renaissance town with palaces, churches and piazzas. As well as historic buildings, which are well worth a visit, Pienza is a mosaic of wonderful little alleyways lined with flowers and artisan shops inside which their owners are busily at work. And don’t miss the magnificent views from the walkway which runs round the edge of the Piazza. Pienza was declared a World Heritage site in 1996 and in 2004 the entire valley, the Val d’Orcia, was included on the list of Unesco’s World Cultural landscapes

Montalcino (24km south west)


Montalcino perches very high up on a hill overlooking olive groves and the famous Brunello vineyards. Surrounded by walls, thelittle streets and walkways are a treasure trove, especially the main street, with its lovely shops and restaurants, which leads to the Piazza del Popolo, the medieval centre of the town.

The Brunello wine is one of the finest red wines in Italy and there are plenty of opportunities for a tasting! The market on a Friday morning is highly recommended with both food and general goods.

Montepulciano (26km south east)


Montepulciano, famous for the excellent Vino Nobile di Montepulciano and Rosso di Montepulciano, sits high up on a hill and a walk up the winding main street to the magnificent Piazza Grande at the top is well worth it. Within its walls little building has been done since 1580 and yet it is beautifully maintained and has a myriad of shops, bars and restaurants without seeming to be particularly overtaken by tourism.

Food and general markets take place on Thursday and Saturday mornings at the bottom of the hill with an antique market in the Piazza Grande on the 2nd weekend of the month.

Bagno Vignoni (29km south)

Bagno Vignoni is a beautiful and very well preserved small village best known for its hot springs. The village is situated around a large Roman bath filled with steaming water which was a stopping off point for the pilgrims travelling to Rome in the 12th and 13th centuries. Today the bath itself is no longer used by the public but you can enjoy the thermal waters down below the village as well as a drink and something to eat in one of the lovely restaurants or cafes.

Montichiello (23km south east)

Montichiello is a tiny village close to Pienza in the heart of the Val D’Orcia first mentioned in a document in 973. From the city gates at the entrance to the village there are stunning views across the valley to Pienza and once through the gates you are immediately absorbed into this tiny community whose homes are adorned with flowers. The Church of St Leonardo and Christoforo which dates back to the 13th century is well worth a visit and there are some lovely places to have something to eat and drink.

Sinalunga (15km north east)

Sinalunga is a small industrial town dating back to Etruscan times and best known to its visitors for its wonderful Tuesday morning market, which is well worth a visit. The old part of the town, which is where the market takes place, is at the top of a very steep hill whilst at the foot of the hill you will find the railway station with trains to Arezzo, Siena and Chiusi. There are also a number of shops in this area and then slightly further away are the supermarkets and a small shopping mall. Let me know if there is anything in particular you need by way of shopping and I shall point you in the right direction.

Foiano (22km north east)

Foiano is a small agricultural walled town which is off the tourist trail but is well worth a visit. Apart from a lovely market on a Monday with stalls set up along the streets, Foiano is famous for its annual carnival which started in 1539 and is the oldest in Italy. Like Montisi, Foiano is divided into 4 contrade (districts) which prepare all year to create magnificent colourful floats and compete in the annual competition in February and March each year.


There are plenty of markets not too far from Montisi which are well worth a visit if you are in the area:

  • Monday : Foiano
  • Tuesday : Sinalunga
  • Wednesday: Monte San Savino, Castiglione del Lago
  • Thurdsay: Montepulciano, Lucignano, Camucia
  • Friday: Montalcino, Pienza
  • Saturday: Asciano, Buonconvento, Bettole