Montalcino & Chianti: Private Wine Tasting Small Group Tour

Two Tastings in Montalcino's Hidden Wineries, Starting at the Fortress

You spend the morning walking Montalcino's fortress and learning why Brunello di Montalcino commands its price, then taste wines at two small wineries chosen for what you're interested in. The private group format means no crowds and no fixed schedule — your guide adjusts based on how long you want to stay at each stop. You leave with two tastings included and a real sense of how the region's soil and tradition shape what's in the glass.

Step-by-step itinerary

Explore Montalcino and Brunello wine

• Visit medieval town of Montalcino
• Walk 15 minutes in the Fortress
• Learn history of Brunello di Montalcino

The Experience

The fortress walls rise above the medieval town of Montalcino, and that's where the day begins — a short 15-minute walk through stone streets that have watched Sangiovese grapes grow for centuries. Your guide explains what makes Brunello di Montalcino so sought after, the soil that shapes it, the aging rules that protect it. You're standing where the wine's reputation was built, not reading about it in a hotel lobby.

After the fortress, the real work starts: two private tastings at small wineries that don't have tour buses parked outside. These are the kind of places where the owner might pour the wine themselves, where you taste what they actually make instead of what fits a standard flight. The Chianti Classico with its black rooster seal, the Bolgheri supertuscans — each one tastes different because the land underneath is different. Your guide knows which winery to take you to based on what you're curious about, not a fixed route.

The whole thing stays small — private groups only, which means no waiting for stragglers, no raised voices, no feeling rushed through a tasting room. You move at the pace that makes sense for the conversation, whether that's lingering over a glass or moving on to the next stop. It's the kind of tour where the guide can actually listen to what you want to know instead of delivering the same speech to twenty people.

What’s included

• Two wine tastings at selected boutique wineries.
• a 15-minute guided walk through Montalcino's medieval fortress with regional history and Brunello di Montalcino education.
• private group format with no fixed itinerary.

Good to know

Easy physical levelInfants must sit on laps

Operated by Claudia Callegari

Is this one for you?Book this if you want to taste real Brunello and Chianti without the standard tour-group experience — the private format and small winery selection mean your guide can actually respond to what you're curious about instead of moving everyone through the same stops.

Top questions

How long is the fortress walk in Montalcino?

About 15 minutes. It's a short introduction to the town's history and the Brunello di Montalcino region before you move to the wineries.

What's included in the tour?

Two wine tastings at boutique wineries, the fortress walk, and your guide's knowledge of the region. Food and transport are not mentioned in the standard package.

Are the wineries the same every time?

No. Your guide selects which small wineries to visit based on what interests you, so each tour can be different.

What's the difference between Brunello di Montalcino and Chianti Classico?

Both are Sangiovese-based wines from Tuscany, but Brunello comes from Montalcino specifically and has stricter aging requirements. Chianti Classico comes from a larger region and is typically lighter. Your guide explains these differences during the tour.

Can I bring children?

Yes. Infants need to sit on an adult's lap. The tour is suitable for all fitness levels, though there is a 15-minute walk through the medieval town.

Is this tour suitable for wine beginners?

Yes. The guide explains the region's history and what makes each wine distinctive, so you don't need prior knowledge to enjoy it.

How many people are in a group?

Groups are kept small and private only — no large tour buses or fixed group sizes.