One Day, Three Hilltop Siena Towns

The key to any great getaway is location, location and location. And Villa Duchessa boasts one of the best. Only 40 minutes from the cultural glories, history and cuisine of Florence, this Tuscan estate is located near the ancient town of Castelfiorentino. And the truly motivated visitor could visit three of Siena’s most spectacular medieval hilltop towns and castles in a single day.


Villa Duchessa itself is well worth the journey to Italy, nestled  amid its own vineyards and cypress trees, with the glowing colours only found in Tuscany. This old castle owned by an Italian family sometimes serves as a hunting lodge, where boar and peasant are on the menu.


Visitors to the villa won’t have to hunt far for a good wine. They can enjoy the rich reds and crisp whites produced on the estate, served by a warm and accommodating staff, led by a butler who epitomizes the ideal of service. And a local cook in full command of their art guarantees that meals are unforgettable occasions.


This six-bedroom property includes a main house and an annex and can accommodate up to 12 guests and a couple of children. A private swimming pool is set on a beautifully manicured terrace. Inside a spacious living room beckons with a fireplace, beamed ceiling and terracotta floors. The annex also includes a living room on the ground floor, as well as  a double bedroom with shower on the first floor.

If you can manage to tear yourself away from the villa, Florence, as noted, is a short trip away. Also close at hand are three of the region’s most beautiful medieval towns. The walled town of San Gimignano, for example, dates back to the 13th century. It’s famous for its medieval architecture and towers that rise high into the air and offer an impressive view of the valley.


Recognized as a UNESCO World Heritage Site , San Gimignano lets you  step back in time while enjoying  local products, such as saffron and the town’s famous white wine, the Vernaccia di San Gimignano. You can enjoy a great gelato in Piazza della Cisterna, a delicious Tuscan meal and a climb up to the remains of the Montestaffoli fortress.

Also within striking distance is the walled castle of Monteriggioni.The castle was built by the Sienese in the 13th century.  Its strategic location atop a hill overlooking the Cassia Road allowed the castle to control the cities of the Val d’Elsa and Staggia and spot any armies approaching Siena. The intact fortified wall includes 14 towers, where guards used to walk patrol.


Entering through the Franca or Romea Gate, you will find yourself in a charming small village, in the  Piazza di Roma, onto which the Church of Santa Maria Assunta faces. Built at the same time as  the castle, the church is done in Romanesque and Gothic style. Centuries ago, the piazza was a large vegetable garden that provided essential food when the castle  came under siege.

And finally there is one of Italy’s most visited cities, the capital of the province, also called Siena. Set on three hills and surrounded by olive groves and the vineyards of Chianti, medieval Siena is stunningly beautiful and famous for its cuisine, art, museum and the Palio,  a horse race held twice a year.

The Palio di Siena is a traditional medieval horse race run around the Piazza del Campo July 2 and August 16. The event is attended by large crowds, and is widely televised. Seventeen Contrade (city neighborhoods) vie for the trophy: a painted banner, or Palio bearing an image of the Blessed Virgin Mary. During each Palio period, the city is decked out in lamps and flags bearing the Contrade colours.


Start your explorations of Siena from the Piazza del Campo, through the winding streets and the city’s historical centre. The Palazzo Pubblico, the red brick city hall that overlooks the Campo, is worth a visit. Or head over to the Piazza del Duomo and buy yourself a pass to visit the inside of the cathedral, the baptistery, the Museum of the Opera del Duomo, with its great views of Siena, and the crypt.

Yes you can visit these three medieval treasures in a day from your base at Villa Duchessa. But why hurry? Each of these destinations could be a day trip in itself. Always followed by the return to the comforts and pleasures of your well-located hunting lodge.

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