Every October, when the nets are spread under the trees and the sharp green smell of fresh-pressed oil drifts from the frantoi in the valley, something extraordinary happens in the hills of Montalcino. It is the season of Olio Novo, the most exciting moment in the olive oil year, and we want you to live it from the inside.
This is not a tasting in a showroom. This is the real harvest. You will stand among centuries-old olive trees with the farmer, pick the olives with your hands, load them on the truck and follow them to the frantoio to watch the thick green stream of fresh oil flow out of the machine for the first time. You will taste it straight from the spout, still warm, peppery, alive, and you will understand in that moment what olio novo really means.
Small groups, maximum 12 guests. Our team of local food and wine experts will be with you from start to finish. Come pick the olives with us. Come taste the season.
Picking the Olives is our most hands-on food experience: four days and three nights based in Montalcino during the October olive harvest, when the hills smell of fresh-pressed oil and the frantoi run day and night.
You will stay at a boutique hotel in the heart of the medieval old town, with the olive groves and the Val d’Orcia just below you. From here everything is within reach – the enotecas, the restaurants, the evening passeggiata along the town walls at sunset.
It all starts in the groves. A full morning picking olives among centuries-old trees with the farmer, loading the crates and following them to the frantoio to watch the thick green stream of olio novo flow out of the press for the first time. You will taste it straight from the spout, still warm, peppery, alive. Lunch is a BBQ right there in the field under the olive branches, with great bottles of wine and the whole crew around the table.
The next day we go deeper into the world of olive oil. At our countryside farm you will cook with fresh olio novo and discover how Italians use it in the kitchen, then sit down for a long family lunch overlooking the Val d’Orcia. In the afternoon we drive to the frantoio to pick up the oil from our olives and do a guided comparative tasting: fresh olio novo, aged oil, commercial oil, side by side. The difference is shocking, and it will change the way you look at a bottle of olive oil forever.
Brunello is never far away in Montalcino. On the first evening a grand comparative tasting with a local wine expert sets the stage, and on the last night we gather at our family farm for a farewell dinner opening old vintages of Rosso and Brunello with the team. These are the moments that stay with you long after you leave.
Everything is taken care of. A private Mercedes vehicle and an English-speaking food and wine expert guide are with you throughout the tour. All lunches are included, the welcome and farewell dinners are included, and for the free evening your guide will recommend the best spots in town and make the reservation for you. You just need to arrive in Montalcino on Thursday and we handle the rest.
The tour runs on two fixed dates in October and is limited to a small group of twelve guests maximum, with a guaranteed departure from four participants. A seasonal experience tied to the actual harvest calendar, which makes it unique and unrepeatable. Once the olives are picked and pressed, the moment is gone. The olio novo you taste today will never taste exactly the same again.
What's included
– Accommodation for 3 nights in an excellent boutique hotel with breakfast
– Private Mercedes Benz luxury vehicle
– English speaking food&wine expert guide-driver
– the olive picking experience with Giovanni at his olive grove
– the frantoio visit and pressing of the olives
– the guided comparative olive oil tasting
– the grand comparative Brunello tasting with Alessandro
– the cooking class
– all the lunches (Friday BBQ lunch + Saturday farm lunch)
– the welcome dinner with us
– the farewell tasting dinner with us
– suggestions for the eventual dinner on your own on day 2
– all the taxes
– our consultancy and help before and during the tour
What's not included
– dinner on Day 2 (we will suggest a few options if interested)
– transfers to/from Montalcino (available on previous request)
Picking the Olives 2026
BENVENUTI A MONTALCINO!
Welcome to Montalcino, the hilltop medieval town that produces one of the greatest wines on Earth: Brunello di Montalcino. You arrive at your own pace and check in at our boutique hotel in the heart of the old town. The afternoon is yours to explore the narrow stone streets, the ancient fortress, the small wine shops where locals pour you a glass without rush.
Take a walk along the town walls: from here you can see the entire valley, the olive groves silvery green against the brown fields already plowed for winter, the rolling hills of Val d’Orcia stretching south towards Monte Amiata. October in Montalcino is harvest time for the olives, and you can feel it everywhere: the nets spread under the trees, the tractors loaded with crates, the sharp green smell of fresh-pressed oil drifting from the frantoi in the valley below.
In the late afternoon we gather at Enoteca Pierangioli, Alessandro’s historic wine shop on the main street, for a grand comparative tasting of Brunello di Montalcino. Different Brunello wines, each from a different soil, a different micro-area, a different philosophy. North slope versus south slope. Clay versus galestro. Young producers versus historic estates. This is the tasting that will set the stage for everything you will drink and eat in the days to come.
Then we move together for our welcome dinner: great local dishes paired with wines of Montalcino. This is where we get to know each other, share stories and start this adventure together.
PICKING THE OLIVES
This is the day you came for. Early in the morning we pick you up and drive into the countryside to reach the olive groves. Giovanni is waiting for us among the trees, centuries-old trunks twisted by time, branches heavy with olives turning from green to dark purple. After a brief introduction to the tools and the technique, we get to work: hands reaching into the branches, rakes combing the leaves, olives falling into the nets below one by one. The sun is warm, the air smells of earth and crushed leaves, and the rhythm of the work takes over – simple, physical, satisfying.
By midday the farmer fires up the grill right there among the trees. This is how it has always been done during the harvest: a long BBQ lunch in the field, sitting on crates and benches under the olive branches, eating grilled meat and vegetables, bread with fresh oil, local cheese, while the work pauses and the wine is poured. We open great bottles and enjoy them the way they are meant to be enjoyed – outside, with dirty hands, surrounded by the land that made them.
After lunch we load the crates of olives onto the truck and follow them to the Frantoio, the Olive Mill. Here the magic happens: the olives are washed, crushed, pressed, and within minutes you see the thick green stream of olio novo flow out of the machine for the first time. The smell is extraordinary – peppery, grassy, alive. You taste it straight from the spout, still warm, burning your throat with that unmistakable kick that only fresh-pressed oil has. You understand in that moment what olio novo really means: not a product on a shelf, but something alive that was still on the tree a few hours ago.
We drive you back to the hotel in the late afternoon for a well-deserved rest. The evening is free for you to wander around Montalcino Old Town at sunset, maybe a glass of wine in the piazza, maybe a quiet dinner at one of the trattorias we will recommend, all within a short walk from your hotel.
COOKING WITH THE OLIO NOVO
This morning we drive a few minutes into the countryside to Locanda Demetra, Giovanni’s family farm surrounded by olive groves and vineyards with a wide view over the Val d’Orcia. His brother is waiting for us in the garden. We start with a visit of the vegetable garden and the herb beds, learning about the raw materials and the flavors that define Tuscan cooking. Then we move to the kitchen for a hands-on experience focused on how Italians use EVO oil extensively in their cuisine: you will prepare classic Italian dishes with your hands, discovering how fresh olio novo transforms even the simplest ingredients into something extraordinary.
Later we sit down for a long family lunch under the shed, with a view on the rolling hills that never gets old. Everything on the table comes from the farm and the land around us, paired with the wines of the estate. This is not a restaurant meal, this is like eating at someone’s home, the way Italians do on Sunday when the whole family gathers.
In the afternoon we drive to the olive mill to pick up the fresh oil pressed from our olives, the very ones we harvested yesterday. Here comes the moment that will change the way you think about olive oil forever: a guided comparative tasting, side by side. A couple of fresh olio novo just pressed in the last days, a fine aged oil from the previous year still in great shape, and a standard commercial oil from the supermarket shelf. The difference is shocking. You will learn to recognize quality, to understand what freshness tastes like, and you will never look at a bottle of olive oil the same way again.
We drive you back to the hotel for some rest. In the evening we gather one last time for our farewell dinner at our favorite Trattoria with Chiara, Giovanni and Alessandro and we open old vintages of Rosso and Brunello di Montalcino, bottles with stories to tell. It is a dinner you will remember for a very long time.
ARRIVEDERCI!
After these intense days together you will leave Montalcino with green-stained hands, a full heart and a new understanding of what olio novo truly is. Not just a condiment, but a season, a gesture, a way of life tied to these hills.
After check-out we can help you with transfers to your next destination, whether it is Florence, Rome, the coast or another corner of Italy. Or perhaps you will want to stay a little longer… Montalcino has a way of not letting you go.
Pickup Points: Montalcino, ask for a different pickup.
Departures: October 8 and 15th, 2026
Season: Fall
Would you like to modify this tour or design your own experience in Tuscany?
Let us know your needs and wishes and we will tailor the perfect program for your trip to Italy.
