Introduction
Casole d’Elsa is a charming medieval hill town in the Val d’Elsa region of Tuscany, rich in history and well worth visiting. It's perfect for visitors who want a blend of history, art, countryside views, and authentic village life. Its compact size makes it an easy day trip, but its atmosphere and surrounding landscapes invite you to linger. It also happens to be where I grew up and went to school, so it has a special place in my heart.
Set on a ridge west of the Elsa valley, still framed by the medieval walls, Casole d'Elsa has several good restaurants, cafes, a couple of grocery stores, a butcher and an excellent ice-cream shop. There is one main street that runs the length of the town and during the summer it's closed to traffic, so that everybody can walk up and down - particularly the teenagers - checking each other out.
This is know as doing 'le vasche' or doing lengths. To do a 'vasca' correctly you walk from the the old town hall all the way down to "Luciano's Bar" (Bar Barroccio) and then back again. As an encouragement Antonella, close to the Town hall, sells excellent ice-cream, and Bar Barroccio at the other end of the village makes very good Aperol Spritzes.
There are smaller side streets that are a delight to explore, and a path on the west side of the village that's perfect for evening sunset walks.
History & Etruscan Roots
Casole’s history goes back to Etruscan times, as shown by archaeological finds from local tombs. You can still visit some of these tombs, like the local "Tomba dell'Agresto", close to Agriturismo Elvira, and you can see many of the finds in the villages small museum.
Later a Roman and Lombard settlement, it eventually became a fief of the Bishops of Volterra before being taken by the Republic of Siena in the 13th century. The town’s well-preserved walls, towers, and the Rocca fortress are reminders of its medieval strategic importance. The walls are said to have been designed by Francesco di Giorgio
Architectural & Artistic Highlights
-
Collegiata di Santa Maria Assunta – The main church, consecrated in 1161, mixes Romanesque and Gothic styles. It contains important Sienese artworks, including works by Marco Romano and Rutilio Manetti. Look out for the statue of "Il Porrina" by Marco Romano, high on the left wall.
-
Church of San Niccolò – Home to 14th-century frescoes by the Rustici brothers and a fine Madonna altarpiece.
-
Town Walls & Gates – Walk along the walls for sweeping views of the Val d’Elsa and spot the round towers and Guelph-battlemented gates. The village used to have an impressive gate but it was sadly blown up during the second world war.
-
Nearby Romanesque Churches – Visit the Pieve of San Giovanni at Mensano or Pievescola for carved capitals and rural charm.
Civic Museum & Archaeology
The Civic Museum of Archaeology and the Collegiate Church is startlingly good, a must-see. Its Etruscan section houses the Bargagli Collection with funerary urns and bronze artefacts. The art gallery includes some beautiful paintings by Alessandro Casolani, of the Sienese school, as well as later 19th-century work reminiscent of the Macchiaioli, a Tuscan version of the impressionists.
The Via Francigena
Casole d’Elsa lies close to the historic Via Francigena pilgrimage route, which connected Northern Europe to Rome in the Middle Ages. Today, walkers and cyclists can enjoy sections of the trail that pass nearby, with well-marked paths, refreshment points, and accommodations for modern pilgrims.
Nature & Countryside
Surrounding Casole are rolling hills, vineyards, and the wooded Montagnola Senese. Several walking and cycling routes start from the village, offering views over the Val d’Elsa and the Berignone forest. Sunset walks along the walls are especially beautiful.
Food & Wine
There are several restaurants in the village, all good. Local products include Sangiovese-based wines, extra virgin olive oil, honey, and seasonal specialties like chestnuts and truffles. There are several trattorias where you can enjoy ribollita, pici pasta, or wild boar stew, paired with a glass of Chianti Colli Senesi.
Osteria Casolani
This is half-way down the high street and has an excellent reputation, as well as a very good wine cellar. Sirio and Nicola are both keen wine-buyers and can give good advice on which wine to accompany your meal.
Ristorante Pizzeria Il Porrina
This is a lovely restaurant and Pizzeria close to the church. It's been going for decades, always run by the same family, now by different generations than when they started. There is an inside room but in the summer everybody eats outside under a large canopy they've set up.
Ristorante Il Colombaio
Outside the village and down the hill on the road towards Volterra - but still walkable from the village. This is a recent addition and has become very popular.
Sadly we have lost "Dal Brigante", the lovely pizzeria with amazing views run by Luciano and Brigante. They decided to retire.
Festivals & Events
During the summer there are often concerts and events - we even have our own Palio, as horse race up the hill in front of the village.
- Palio di Casole d’Elsa – A horse race usually held on the second Sunday of July, a competition between the local villages for a "Palio", the banner that is the prize. After the race there's an excellent outdoor roast dinner with long tables set up for all the village.
- Living Nativity – Every two years the village puts on a fabulous 'Living Nativity' where everybody dresses up to re-enact the nativity and all the neighbouring villages come to have a look. Sometimes it's a Nativity, other times it's an Easter procession
- There are often concerts organised, from open air opera, classical music and more, as well as exhibitions and markets.
Below is a drawing of mine from 1995 of the small cloister of San Cristoforo where concerts are sometimes played.
Practical Information
To reach the village of Casole d'Elsa, close to Siena, first you have to get to Tuscany. This page will be useful: How to get to Tuscany. Once in Tuscany the easiest way to reach Casole is by car; it's a pity but the village isn't well served by public transport at the moment. It will take about 1hr and a half to drive to Casole from Pisa Airport (PSA), and just an hour to drive there from Florence Airport (FLR).
There is parking available near the walls and a lift to bring visitors up into the town. Public transport is possible (but sporadic) via buses from Colle di Val d’Elsa. The town is walkable but hilly, so comfortable shoes are recommended.
This is a Three-Words link to the lower car park, which is free and has some EV charging points:
Lower Car Park
While this 3 words will take you to the upper car park, which is chargeable but is closer to the lift that can help get into the village above:
Upper Car Park
You can also drive up into the village but the road is sometimes blocked off (in the evenings during summertime, for example) and parking spots are tricky. If you're staying in Dan's House you'll have a parking spot below the house, while if you're staying in Agriturismo Elvira (Pinolo, Noce etc.) then you can easily walk into town.
Where to stay
We have plenty of houses in the area - these can be perfect for an out of season escape, a relaxing autumn stay or even a May half-term trip with the kids. Have a look at Pinolo for a place with a pool nearby.
Insider Tips
- Climb the Rocca tower for one of the best panoramic views.
- Visit in the early evening for a stroll at golden hour and aperitivo in the main square.
- Explore nearby hamlets like Mensano or Monteguidi for a quieter, off-the-beaten-path experience. Monteguidi is a tiny village that is, rather surprisingly, marked on one of the great maps in the Vatican Hall of Maps.
Author: Dan Wrightson
Dan Wrightson grew up in Tuscany, Italy and has been writing about, sketching and exploring Tuscany and Italy since 1983.
5th Dec 2024 13th Sep 2025