There’s no doubt that the surroundings of Siena offer some of the most beautiful and charming destinations in Tuscany. These landscapes are simply unforgettable, with the Chianti wine region to the north of Siena and the areas of Crete and Val d’Orcia to the south, the flagships of Tuscan idyllic country landscape.
So for anyone who’s thinking of heading there, here’s a quick guide to the most charming small towns and villages you can find near Siena. These are places you can reach by car within an hour. As some of these are small towns, it’s worth remembering that not all of them are easily accessible with public transport.
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10 Beautiful Small Towns to Visit near Siena
1. San Gimignano, the most famous small town near Siena
The most famous of all small towns to visit near Siena. With its famous silhouettes and beautifully preserved Medieval historic centre, San Gimignano – known as the “Manhattan of the Middle Ages” – welcomes visitors with a lively vibe, frescoes to admire in the 12th century Cathedral, a few museums, shops with interesting offerings, the Award-winning Gelateria Dondoli and plenty of trattorie. => Get the best of this Medieval gem with our guide to the Top Things to do in San Gimignano.
Distance from Siena: 1 hour – There’s a direct bus from Monday to Saturday.
2. Monteriggioni
Located on the Superstrada RA3 between Florence and Siena, the walled village of Monteriggioni speaks of a time when battles between these two cities were an everyday event. The massive walls that still encircle the town are the first memory of that turbulent time, and so is the small but fun Museum Monteriggioni in Arme. A few streets and a couple of good restaurants complement your time travel experience.
Distance: 30 minute drive – there’s a direct bus from Siena.
3. Pienza
Known as the ‘Ideal City’, Pienza was completely rebuilt in the Renaissance, by famous architect Rossellino. The job was given to him by the Pope Pio II Piccolomini, who was born here (he’s the one who has a series of frescoes in the Siena Cathedral dedicated to him). So when you walk around the piazza del Duomo and visit Palazzo Piccolomini, you can see what a Renaissance city was all about. Maybe not an ideal city, but lovely indeed. Definitely one of the most beautiful small towns to visit near Siena.
Distance: 1 hour and 10 minute drive – no direct bus, you need to change at Buonconvento.
4. San Quirico d’Orcia
Not far from Pienza, at the heart of the Val d’Orcia lies the small town of San Quirico d’Orcia, one of our personal favourites. Once an important stop on the pilgrim road via Francigena, it has a few churches to testify its past, a peaceful lovely atmosphere and some nice shops and trattorie. All around it, some of the most idyllic views and scenic drives in Tuscany.
Nearby => see Bagno Vignoni, with its main square that is a thermal water pool.
Distance: 1 hour drive – there’s no direct bus.
5. Montalcino
One of Tuscany’s hilltop towns famous for its wine, Montalcino watches over the beautiful Val d’Orcia and the Mount Amiata. Visit the Medieval Priori Palace, the Museo Civico with sacred art (mainly Medieval and Renaissance) and browse around the many wineries and cellars to taste the prized Brunello di Montalcino red wine.
Nearby-> Don’t miss the Sant’Antimo Abbey for a taste of Medieval art.
Join this Montalcino Small-Group Wine Tasting Tour from Siena to try some delicious local wine Rosso and Brunello di Montalcino, visit a family-run winery and enjoy a traditional lunch.
Distance: 1 hour drive – no direct bus, you need to change at Buonconvento
6. Radda in Chianti
More wine tasting awaits the traveller in Radda in Chianti. Located at the heart of the Chianti wine region, famous for its beautiful views, villas, castles and wine estates, Radda is more about the landscape and the wine than sightseeing. It’s an occasion to try some of Chianti’s special dishes, and the perfect place to live la bella vita, in perfect Tuscan style. For wine lovers, a must-see and one of the favourite small towns to visit near Siena
Distance: 45 minute drive. There’s a direct bus to Siena that takes 1 hour.
7. Montepulciano
The third ‘wine queen’ of Tuscany, the hilltop town of Montepulciano boasts a beautiful main square with a palace that looks like Palazzo Vecchio in Florence, and an intriguing stone well with lions and griffins decorations. Many lovely shops and restaurants enliven this welcoming town, where one of Tuscany’s top red wines is produced, the Nobile di Montepulciano. Needless to say, here you have plenty of opportunity for wine tasting. Bring comfy shoes as the streets are quite steep!
Visit one of the world’s most beautiful cellar with this Montepulciano Wine Tasting Tour. See rows of large oak barrels and learn how the famous local wines are made. Taste Supertuscan, Nobile, and Nobile Riserva. An unforgettable experience!
Distance: 1 hour 5 minute drive. There’s no direct bus from Siena.
8. Colle val d’elsa
Colle Val d’Elsa is located a short distance north west of Siena, along the Superstrada RA3 to Florence. A lesser known town, but well worth a visit if you are in the area. The old part of town that maintains some Medieval architecture, crowns the hill, while lower down you find the modern part. Aside from some lovely vistas, Colle di Val d’Elsa is mostly known for its crystal glass production, and you find a few artisan workshops that show off the local craft. Plus there’s a range of very nice restaurants and an interesting Cathedral.
Distance: 35 minute drive – There’s a direct bus from Siena.
9. Cortona
The famous ‘town under the Tuscan sun’ is still as lovely now as it always was. The backdrop to Frances Mayes’ famous novel, Cortona still attracts expat and travellers that come here for its beautifully preserved Medieval centre, its art museums and Etruscan rests. Plus, it hosts a range of festivals and events throughout the season – like the famous antiquity fair at the end of August– making it one of the most beloved destinations in the region and a popular day trip from Siena.
Distance: 1 hour drive. There are not direct buses from Siena.
10. Lucignano
Not far from Cortona lies the small town of Lucignano. Less famous than other Tuscan hilltop towns, it’s worth a visit for the interesting city plan that comes straight out of the Middle Ages. At that time the town had an important strategic role between Siena and Arezzo, dominating the Val di Chiana area. The Palazzo Comunale with its small museum stand as witnesses to that storied past. Here you’ll find a very intriguing artefact indeed – the romantic Tree of Love.
Distance: 45 minutes drive. There’s a direct bus from Siena, that takes 50 minutes.
N.B -> Not to be confused with the hamlet of Lucignano in the Chianti, this one is in the province of Arezzo.
More Trip ideas? => See 5 Unmissable Medieval Wonders near Siena
More small towns to visit near Siena? => Check out fascinating Volterra, with its Etruscan museum and alabaster workshops. Or the tiny village of San Gusmè, surrounded by the Chianti landscape.
Author: Sabrina Nesi, founder of Lovefromtuscany.com, passionate about sharing the beauty of Tuscany and Italy with the world.
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