Five beautiful hilltop towns in Tuscany

Five beautiful hilltop towns in Tuscany

Holidaymakers who have visited our property in the beautiful village of Stigliano will know just how enchanting Tuscany is. With endless blue skies, acres of vineyards and a breathtaking, rolling landscape, it’s no wonder people come back to this spectacular region again and again.

The Tuscan hills are dotted with charming towns and villages, from Stigliano itself to the many delights of Siena. However, these are just the start of the many hilltop gems to be found in this beloved part of Italy. We’ve picked five of our favourites, all an hour or less from our Tuscan property, to help get you started.


Built between 1213 and 1219, Monteriggioni castle was originally constructed to be a lookout for any armies approaching Siena, while also controlling the cities of Val d’Elsa and Staggia. Over time, homes, shops and much more sprung up within its walls, creating a typical fortified village. Today it’s remarkably well-preserved. In fact, the village and its walls have remained more or less the same over the centuries, with narrow cobbled streets and ancient stone buildings.

The perfectly rounded shape of Monteriggioni looks almost artificial, although in reality it follows the natural curve of the hill. Visitors can leave their cars in the car park at the bottom of the slope, then climb the short trail to enter the village through the France or Romea Gate. Due to its small size, it will only take a few minutes to reach the ancient centre of Monteriggioni, where you’ll find the Piazza di Roma, Church of Santa Maria Assunta and the rest of the castle. Make sure to take the time to visit the Armoury Museum or take a short stroll around the village’s famous walls.

Colle di Val d’Elsa

This delightful town, also known as the Hill of Elsa Valley, is well-known for its narrow, winding lanes and the creation of beautiful crystal glassware. It also has great views over Tuscany, some fantastic restaurants and a unique, historical feel throughout. 

The town is split into two parts – the old town at the top of the hill and the newer areas below. There is plenty of parking throughout, including a very convenient car park at the historical centre. The older part of town is where you will find most of the attractions, including the Archaeological Museum, the Duomo and several traditional restaurants.  On the first Sunday of every month visitors can also enjoy an open-air glass blowing and engraving demonstration close to the Duomo. If that catches your imagination, the Crystal Museum in the lower town is a great place to learn more about how the town produces its delicate decorative pieces.


One of many unmissable locations for wine enthusiasts is Montalcino, where the famous Brunello di Montalcino is produced. The beautiful spot is surrounded by vineyards producing this famous beverage, which is one of the most sought-after red wines in Italy. As for the village itself; the medieval settlement is surrounded by 13th Century walls, giving it a contained, magical feel amongst the expanse of the Tuscan hills.

Montalcino is the kind of place where the real pleasure comes from simply strolling along the main street, enjoying the atmosphere and perhaps stopping for a glass of wine or a coffee in the sunshine. There are many historic sites for you to discover within the town, including the fortress (built in 1361), the Chiesa Di Sant’Agostino and the Piazza del Popolo – the main square with its impressive clock tower. For history and art lovers, there are also some museums to look around, including Museo Civico and Diocesano di Arte Sacra.

San Gimignano 

Known as the ‘Town of the Fine Towers’, San Gimignano is famous for its medieval architecture. The town became a UNESCO World Heritage Site in 1990 and is best known for the impressive and well-maintained towers which stretch high above the rooftops. Today only 13 of the original 65 towers remain standing, but they still manage to make the view approaching San Gimignano somewhat iconic.

Once you're inside the city walls, it’s time to turn your gaze back to ground-level. Visit the stunning Collegiate Church of San Gimignano, with its many frescos, as well as the Palazzo Comunale for a look at some medieval artwork. If you’re willing to work for your views, why not climb the 218 steps to the top of the Torre Grossa, the highest tower in town? Last but not least, find a place to sit down and enjoy a refreshing glass of Vernaccia di San Gimignano. This white wine is produced exclusively in San Gimignano and is one of the top wines in Tuscany.


Balanced precariously atop a limestone ridge, Montepulciano is a classically beautiful Tuscan town. The town is most famous for its food and drink, with several beautiful vineyards producing Italy’s classic red wine, Vino Nobile.

Montepulciano is also known for its beauty – it was chosen as one of the filming locations for the Twilight ‘New Moon’ film. This brush with fame has increased the town’s popularity, although compared to the larger cities it remains very peaceful, even in peak season. The panoramic views can be enjoyed throughout the town and offer some unmatched glimpses of the surrounding countryside.

Montepulciano’s most spectacular place to visit is the Piazza Grande, which contains the town hall and unfinished cathedral. However, the whole town is extremely easy to walk around, with plenty of little shops and restaurants to duck inside. There are also a couple of beautiful churches which are worth visiting; see a masterpiece from the Sienese school in the Cathedral of Santa Maria Assunta or an elaborate altarpiece in the Church of Santa Lucia.

With so many charming spots within easy reach of Stigliano, you certainly won’t run out of things to do. However, when you’re done exploring, or if you just want a day to relax and recharge, then a comfortable holiday property is a must. Our Stigliano property has a wonderful collection of holiday studios, apartments and cottages, all set within expertly converted historic buildings. 

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