Take day trips from Siena to some of Tuscany‘s most beautiful sights. From the Medieval masterpiece that is San Gimignano, to Monteriggioni and the ideal city of Pienza. These are the treasures of Tuscany to be found just a stone’s throw from Siena.

=> 12 Top Things to do while you’re in Siena

Day trips from Siena – in search of small Medieval towns


If you’re in Siena, Medieval towns must be your thing, so Monteriggioni is a great place to go nearby. It’s a small town that started life as a castle to defend Sienese territory, and today it’s still completely surrounded by a set of impressive walls. Seen from afar it looks like a crown set on top of a hill. Images of films come to mind, of ancient battles and knights. Inside its narrow stone streets and towers poking up from behind the houses can’t fail to delight you.

Monteriggioni – photo @sferrario1968 on pixabay

San Gimignano

This is one of the most popular day trips from Siena. And the most famous of all Tuscany’s hilltop towns. San Gimignano has the nickname “Manhattan of the middle ages”  for its 14 Medieval towers that are still standing today. It’s a pretty unique sight even by Tuscan standards. Once you’ve stepped inside the impressive gate, you can visit the Cathedral whose walls are alive with frescoes, climb a tower and browse the lovely shops. If this is not enough to get into the Medieval swing of things, the Torture Museum won’t fail to impress you.

top things to do in san gimignano

San Gusmè

If if would like to get away from it all, head to the Chianti region and you’ll find the tiniest village you could possibly imagine. San Gusmè is a miniscule fortified village, basically one cobbled square and a couple of restaurants. All around it is the typical Chianti view, perfectly combed vineyards and winding roads dotted with cypress trees. The landscape is breathtaking, the atmosphere so peaceful that a stop here will reconcile you with the world.

=> 7 Good reasons to visit the Chianti region and the Best Things to do during your stay in the Chianti!

Nature and art combined at the Chianti Sculpture Park

Do you like the idea of a bit of contemporary art in the midst of the Sienese countryside? If the answer is yes, then a visit to the Chianti Sculpture Park is a must. This park has installations from contemporary artists from all aver the world. Their art pieces aim to interact with the natural world. Sometimes weird, sometimes funny or reflective, this unusual museum offers a different view of the well-known Tuscan landscape. If you and the family want a bit of fresh air and culture, this is the place for you. It is located near Pievasciata, 20 kilometres north of Siena.

Discover the magic of San Galgano Abbey

The ruins of the Gothic Abbey of San Galgano lie 20 km. south of Siena. It’s a sight that won’t leave even the most worldly traveller unimpressed. The atmosphere, the natural setting, the light that caresses the ancient ruins, everything contributes to make this place special.

A once powerful monastery, the abbey recalls a Medieval past that has left us a legend, the one of Saint Galgano. This knight, tired of all the violence and war, thrust his sword into a rock. It’s still here today, at the nearby Montesiepi Chapel. A classic Medieval legend embedded in the Tuscan stone.

day trips from siena
San Galgano Abbey – photo @skitterphoto on pixabay

Explore the ideal city Pienza, in the Val d’Orcia

Pienza is a real delight. The town has a curious history, as it was born from the desire of Pope Pius II to create an ‘ideal city’. Wanting to be remembered, this ambitious pope gave his home town Corsignano a new name, Pienza (‘city of Pius’). The renowned Renaissance architect Rossellino was employed to remake the town completely, and the result is what we see today. There’s a graceful Cathedral in the main square, and the elegant Palazzo Piccolomini. One of Tuscany’s best pecorino cheeses is produced and sold here.

A visit to Pienza is one of the most rewarding day trips from Siena. Around the Val d’Orcia there are some of the most scenic drives in Tuscany.

=> What to pack for Tuscany