gather your tribe

Ideally situated between Florence and Siena, the natural setting of our estate offers complete privacy while remaining a stone’s throw from Tuscany’s major attractions, historic sites, restaurants, and wineries. Our villas have been lovingly restored to provide modern comforts in a historic setting. We offer guided tours of our wine cellar and tastings of Podere Ciona vintages and recommendations for the best restaurant and food purveyors in the area. For explorers, we provide suggestions on hiking and cycling tours of the Tuscan hills and tips for discovering the treasures of nearby Florence and Siena.

the GUESTHOUSE

the village of montegrossi, gaiole-in-chianti

Perched on one of the highest hills between Florence and Siena, La Casa di Montegrossi commands sweeping views across the Chianti countryside — vineyards and olive groves rolling southward toward the distant towers of Siena. This is Tuscany as you've always imagined it.

The house itself is a 500-year-old Tuscan farmhouse — a casa colonica — painstakingly restored to offer every modern comfort without sacrificing an ounce of its soul. Thick stone walls, ancient timbers, and centuries of history surround you; fast Wi-Fi and eight en-suite bedrooms mean you never have to rough it.

La Casa is built for gathering. With space for up to 16 guests across the main house and a private guest apartment, it's the rare property that brings extended families and large groups together without anyone feeling crowded. At the heart of it all is a courtyard shared between the two — the natural place to end every evening, gathered around a roaring fire under an open sky.

That same courtyard is home to a fully restored 13th-century forno — a wood-fired pizza oven and bread oven that quickly becomes the social center of any stay. Fire it up for homemade pizza, fresh-baked bread, or slow-roasted meats and vegetables, and you'll understand why Tuscans have been cooking this way for centuries.

History runs deep here. The medieval tower near the property once stood as the southernmost Florentine outpost during the wars between Florence and Siena — a reminder that the hills you're looking out over have been fought over, loved, and lived in for a very long time.

Gaiole-in-Chianti, with its shops, restaurants, and everyday essentials, is just ten minutes away. Florence lies 60km to the north; Siena, just 30km south. And within easy reach are some of Italy's most breathtaking medieval cities — San Gimignano, Arezzo, Perugia, Lucca, Pisa, and Assisi.

On warm Tuscan afternoons, the pool is where time slows down. Set among ancient olive groves, it's a place to cool off, drift, and let the stillness of the Chianti hills wash over you — with nothing on the horizon but silver-green leaves and open sky. Whether you're swimming laps at dawn or lingering with a glass of wine as the sun dips below the hills, the pool sets the rhythm for the kind of day Tuscany was made for.

La Casa di Montegrossi isn't just a place to stay. It's a place to be in Tuscany.