For centuries men have dominated the Tuscan wine industry. However, as more daughters take over the wineries from their fathers it is creating a natural diversity at the regional wine meetings as well as in the particularities of the wine.

Luigi picked us up for the brief drive to Villa Sant’Anna, owned and managed by Simona and her daughters, Anna and Margherita. The winery is nestled in the heart of the historic Nobile di Montepulciano. Sant’Anna is known for the finesse and quality of its wines. We were greeted by Simona who would be our host. Over a tasting consisting of salamis, cheese, zucchini, olive oil produced on the estate, and bread, Simona shared detailed information about not only their wines but the running of the estate. As we were learning throughout Tuscany, wine making at Villa Sant’Anna was personal. Following the tasting we made arrangements to have a case of wine and a few bottles of olive oil shipped home.

Luigi’s navigation was challenged by the tight turns leading to the medieval village entrance of Monticchiello (population 200) which took on its current day appearance back in the 1200s. Our lunch reservation was at Osteria La Porta located just outside the village gate. Daria Cappelli, the owner, greeted us as we entered the osteria. Daria began her business as a bar in 1997, initially enlisting her mother to cook, until the business grew into Osteria La Porta. After being seated on the terrace overlooking the Val d’Orcia we ordered bruschetta to share. You could taste the warmth of the sun in the tomatoes piled on top of the grilled bread and drizzled with the locally pressed olive oil. Nothing but a Nobile di Montepulciano Riserva would do for this meal! Our main course consisted of roasted venison with a fresh salad of rocket and parmesan which was followed by an exquisite panna cotta with basil and mint. The symphony of flavors was the masterful expression of Tuscany in May.

After lunch, we enjoyed a brief stroll down the lanes of Monticchiello. I found the following excerpt from Iris Orgio’s “War in Val d’Orcia” diary particularly descriptive of the type of people who live in this small village: April 10, 1944 Entry: “Hear further details of the ‘battle of Monticchiello’. It appears to have been in the best medieval tradition – the partisans having taken up their position behind the old walls of the little city, the Fascists attacking. There were about two hundred and fifty Fascists, and a hundred and twenty partisans. The local population took an active part, the younger women helping the partisans with the loading, the old ones bringing in eggs to refresh the combatants. . . . After eleven hours of fighting, when the Fascists were already disheartened, the partisans made a sally down the hill – the women on the ramparts shouting, forza, ragazzi! – and the Fascists ignominiously turned tail and fled, leaving some of their arms behind.” 

Since 1967, the village square has been transformed each summer into an open-air theatre (“Teatro Povero”) in which the village writes, stages, and directs plays.  After wandering Monticchiello’s charming cobblestone lanes we travel to Cantine Dei for our 3:00PM tasting. 

The Dei winery was purchased in 1964 by Alibranda Dei. Today, Caterina Dei, the third generation, operates one of the leading, cutting-edge producers of Vino Nobile. After a tour of the winery, built out of magnificent spiraling travertine, we proceed to the small tasting room where we are hosted by Caterina who shared her passion for continuing Alibranda’s legacy of producing quality wines and olive oil. Our tasting consisted of the Vino Nobile di Montepulciano Bossona, Nobile Madonna Della Querce, Sancta Catherine, and the Reserve.

Luigi safely delivered us back to our villa where the fragrance of garlic sautéing awaited the addition of the fresh rabbit for our tagliatelle as we continued to enjoy my 60th birthday celebration in Tuscany. We poured both Sant’Anna and Dei wines as we repeatedly lifted our glasses in salute to the women running businesses with commitment and passion!