There is a Tuscany that most visitors never see. It happens between September and November, when the summer crowds are gone, the light turns golden and the real work of the land begins. Grapes are picked by hand in the vineyards of Brunello. Olives fall into nets under centuries-old trees. Dogs race through foggy oak woods chasing the scent of White Truffle. This is harvest season in Montalcino, and it is the most beautiful, most honest, most alive time of the year.

We have been living these rhythms our whole lives. We know the sweet smell of ripe Sangiovese clusters in September, the sharp green perfume of fresh-pressed oil in October, the earthy intoxicating scent of white truffle in November. And every year we thought: this is too good to keep to ourselves. So we created three immersive experiences, one for each harvest, to share these moments with people who want to go beyond tasting and understand what it truly takes to make the things we love.

Small groups, maximum twelve guests, no spectators: you work alongside the farmers, you eat at his tables, you drink wines that rarely leave the family cellars. Four days and three nights each, all based in our hometown of Montalcino.

BRUNELLO HARVEST – September 17-20 and September 24-27, 2026

September in Montalcino is electric. Tractors come and go, winemakers greet each other in the piazza with purple-stained hands, and the vineyards glow under the late summer sun. This is where wine begins, and for four days you are part of the crew.

With us, you join the winemaker among the rows of Sangiovese, pick the grapes with your hands, carry the baskets to the cellar and press the clusters yourself. You learn about fermentation not from a book but from the man who has been doing this his whole life, standing right where it happens. Then comes the reward: a long harvest lunch under the pergola with the family, homemade Tuscan food, cured meats, pecorino, and old vintages of Brunello opened for the occasion, bottles that money cannot buy.

On day three we go deeper: a barrel tasting drawing wine directly from the casks at different stages of ageing, followed by a grand comparative Brunello tasting led by Alessandro at his historic enoteca. The farewell dinner brings together our team and two local winemakers around a table of stories and old bottles. You will leave with stained hands and a new understanding of what Brunello truly is.

PICKING THE OLIVES – October 8-11 and October 15-18, 2026

October smells different in Montalcino. The nets are spread under the trees, the Frantoi, the live mills, in the valley hum day and night, and the sharp green scent of fresh oil drifts through the cold morning air. This is the Season of Olio Novo, the New Olive Oil, and it is a thing you can only understand by being here.

We will spend a morning picking olives with Giovanni in his grove among trees that have been here for centuries, hands reaching into the branches, olives falling into the nets one by one. At midday a friend fires up the grill right there among the trees: a long BBQ lunch in the field, sitting on crates and benches, eating grilled meat and vegetables, bread with fresh oil, local cheese, while great bottles are poured the way they are meant to be enjoyed, outside, with dirty hands. After lunch you follow the crates to the Frantoio and watch as the olives become thick, green, peppery olio novo right before your eyes. You taste it warm, straight from the press, burning your throat with that unmistakable kick. You understand in that moment what fresh olive oil really means.

The next day you cook with it at Giovani’s family farm, the Locanda Demera, discovering how Italians use EVO oil in everything. Then a guided comparative tasting puts our fresh olio novo side by side with aged oil and a commercial supermarket bottle. The difference is shocking, and you will never look at olive oil the same way again.

TRUFFLE HUNTING FESTIVAL November 5-8 and November 12-15, 2026

Every November, when the first fog rises from the valleys and the oak woods turn copper and gold, something ancient happens in these hills. Men walk into the forest before dawn with their dogs, following invisible trails of scent deep into the undergrowth. They are hunting the most precious ingredient on Earth: the White Truffle of Tuscany.

You go with them. You follow the dogs through carpets of fallen leaves along crystal clear creeks, you kneel beside the hunter as he carefully extracts the truffle from the earth, and the smell hits you immediately: intense, earthy, intoxicating. You understand in that moment why people have been obsessed with this tuber for thousands of years.

At noon the feast begins at the hunters’ headquarters. Their wives have been cooking since morning: handmade pappardelle, fried eggs, crostini, every dish generous with fresh shavings of white truffle. We open many great bottles and sit together for a lunch that is loud, warm, generous, and unforgettable. This is not a refined restaurant experience, this is a celebration among friends in the heart of truffle country. The experience also includes a cooking class focused on fresh pasta and truffle at our farm, and a grand comparative tasting with Alessandro.

What all the three experiences include?

Boutique hotel in Montalcino Old Town for three nights with breakfast, our food and wine expertise guidance, all the hands-on experiences, the grand comparative Brunello tasting with Alessandro, all the unches, welcome and farewell dinners with us and some of the farmers, and our help before and during the tour. Maximum twelve guests per departure. Each experience runs twice on consecutive weeks so you can choose the date that works best. Prices form € 2.200 per person

Harvest season in Montalcino is short and these groups are small. If you have ever dreamed of going beyond the bottle and living the real Tuscany, this is the time.

Write to us and we will help you find the right experience and eventually extend or connect your stay in Italy