Since the 1400s, wine has been made at Montecalvi. For centuries it was part of the Castello di Uzzano estate, owned by Niccolò da Uzzano, a Florentine politician in the Medici era, and latterly owned by Don Briano Carlo Maria Castelbarco-Albani Visconti Simonetta dei principi di Montignano (the Count Castelbarco). Farming throughout this period was done through the mezzadria system, by which local farmers farmed the estate for, and shared the harvest with, the castello.

In the 1980s Montecalvi became an independent estate, and is now owned by the Drake family, owners of Collalto in the Adelaide Hills region of Australia. They have worked tirelessly to update the vineyards, restoring the old vines and replanting with indigenous varieties. Montecalvi is now a certified organic estate.

Montecalvi's vineyards are among the finest in the Chianti Classico area, on a mix of sandstone and clay soils and at an altitude of 250 m above sea level. They are ideally located with south/south-east/south-west exposures. All vineyards are farmed organically and sustainably. In total, the estate comprises 10 hectares, with about four hectares under vine, and half a hectare planted with olive trees.

Le Terrazze, their oldest and finest vineyard, was planted on dry stone wall terraces in 1932, predominantly with Sangiovese, but also a small field blend of Canaiolo, Ciliegiolo, Malvasia Nera and Trebbiano. It is one of the oldest vineyards in Tuscany and each of the old, gnarled vines yields only a handful of grapes, thereby concentrating the aromas and characters.

In the Montecalvi Alto and Basso vineyards, Sangiovese was planted in 1990, and Montecalvi Bosco was added in 2006, planted with Sangiovese, Canaiolo and Canina Nera. The San Piero vineyard was planted in 2003, and is exclusively Cabernet Sauvignon. Il Pozzo vineyard was planted in 2019, exclusively to Ciliegiolo. Whilst the estate's main focus is on Sangiovese, they dedicate the same amount of care to the other varieties and all are harvested, fermented and aged separately. In this way the distinct character of each variety is nurtured so that, when they make the final blends, the wines become much more than the sum of their parts.

Winemaking is done by Tim Manning, whose career spans more than two decades. During that time, he has produced wine and tended vines in New Zealand, the USA, various parts of Italy, including, of course, Tuscany. The Drake family is convinced that Montecalvi’s intimate size lies behind the success of their wines. The team knows the vineyards like the back of their hand, helping them to tend to each row, vine, and bunch individually.