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Castello di Casole is one of the most prominent and ideally located estates in all of Tuscany. Those that know the region best treasure this particular locale for a myriad of reasons.

First, the estate is central to the most desirable Tuscan destinations. Idyllic Siena is just 20 minutes east, and Florence 45 minutes north. The coast is a scenic hour’s drive. The popular Volterra and Montalcino are within one hour’s drive. The walled fortress of Monteriggioni is a comfortable bike ride. Our nearby neighbors are the hill towns of Mensano, Radicondoli and the namesake, Casole d’Elsa.

In the distance, the legendary towers of San Gimignano rise on the horizon. To know Tuscany intimately, each cobbled street by cobbled street is life’s great reward.

Casole d’Elsa

The namesake of Castello di Casole is a beautiful, quiet village of ancient brick buildings. There panoramic views around every corner. Originally an Etruscan settlement, the Casole fell under control of Siena in the 13th century. Its many historical buildings make for fascinating touring. Distance from Castello di Casole: 6 miles/9.7 km (and for road bikers, one of the great climbs in the region).

San Gimignano

Perhaps the most medieval of any destination in Tuscany, this easily walkable hilltop town is home to 14 beautiful towers – the remains of more than 70 that once punctuated its skyline. There’s a wide array of 14th- and 15th-century art to be found at spots such as the Museo Civico and the Museo d’art Sacra.

The Museo della Tortura offers a hair-raising collection of historical torture instruments, including some still used around the world today. The 14th-century fortress of Rocca is a romantic ruin offering lovely views of the town. Climb the Torre Grossa – the tallest tower – for incredible views of rooftops and surrounding geography. Distance from Castello di Casole: 12 miles/19.3 km.


A beautifully preserved medieval fortress village on a hilltop surrounded by 13th century walls that have survived almost intact. Dante compared the town’s 14 towers to the Titans guarding the bottom rung of Hell. Monteriggioni has a pretty Romanesque church which faces the piazza and houses a public garden. Distance from Castello di Casole: 5 miles/8 km.

Colle di Val d’Elsa

Originally made up of three independent areas, this medieval town, which dates from the 10th century, has been the scene of more than a few struggles over the centuries. Museums and architecture, including Baccio d’Agnolo’s mannerist Palazzo Campana gate (1539), make it a rich destination. Today it is the crystal capital of Italy. Distance from Castello di Casole: 5 miles/8 km.