Brunello di Montalcino Wine Tour from Siena: 2 Tastings

Brunello tastes the way it's meant to: aged in the cellars where it was born, not poured in a tasting room miles away.

A wine tour from Siena to Montalcino with guided tastings of two Brunello di Montalcino wines at local estates, a professional multilingual guide, and free time to walk the medieval fortress town. The tour includes a scenic drive through Val d'Orcia vineyards, insight into Brunello aging traditions, and a light Tuscan snack with fresh bread and olive oil. Groups stay under eight in a minivan or up to thirty in a minibus, and the full day runs 5.5 hours from Siena Railway Station.

Step-by-step itinerary

Brunello di Montalcino Wine Tour

• Meet staff at Siena train station
• Visit 2 local wineries for tastings
• Enjoy free time in Montalcino village
• Return to Siena

The Experience

You meet the guide outside Siena Railway Station at the clock tower, then drive into the rolling vineyards of Val d'Orcia toward Montalcino, a hilltop town built around a medieval fortress. The route itself is part of the experience — the landscape shifts from the Siena basin into steeper terrain as you approach the Brunello heartland, and the guide explains what you're seeing: why these slopes, this soil, this altitude matter to the wine. Brunello di Montalcino comes only from Sangiovese grapes grown here, and the region's reputation rests on that specificity.

At two carefully selected estates, you taste Brunello di Montalcino wines with the guide walking you through what's in the glass — the aging techniques, the traditions, the decisions that separate one producer from another. Between tastings, you get a traditional Tuscan snack: fresh local bread, extra virgin olive oil, and time to sit with what you've learned. The guide speaks English, Spanish or Italian depending on the group, and translates when needed during the tastings.

After the second winery, you have free time in Montalcino itself. The fortress sits at the top of the town, and the medieval streets below are narrow enough that you can walk them in an hour or spend longer in a café. Some people climb to the fortress for the view across the vineyards; others browse the small shops or sit in the piazza. The guide stays with the group and can point out where to go, but the time is yours. Then it's the drive back to Siena, arriving at the railway station roughly 5.5 hours after you left.

What’s included

• Guided tastings of two Brunello di Montalcino wines at prestigious local estates.
• professional multilingual guide in English, Spanish or Italian.
• scenic drive through the Val d'Orcia vineyards and countryside.
• free time to explore the medieval hilltop town of Montalcino and the fortress.
• traditional Tuscan snack with fresh local bread and extra virgin olive oil.
• insight into Brunello winemaking traditions and aging techniques.
• hotel or railway station pickup and return (meet at Siena Railway Station).

Good to know

Easy physical levelStroller friendlyInfant seats availablePublic transport nearbyInfants must sit on laps

Operated by myTour in Italy

Is this one for you?Book this tour if you want to taste Brunello in the cellars where it's aged rather than in a hotel tasting room, and if you have a free afternoon from Siena — the 5.5-hour round trip leaves room for an early start or a late dinner back in the city. The small group size and English-speaking guide make it straightforward for first-time visitors to Montalcino, and the free time in the town means you're not locked into a schedule if you want to linger at a winery or explore on your own.

Traveler reviews

4.03★★★★★★★★★★

66 verified traveler reviews

5 ★38

4 ★9

3 ★9

2 ★3

1 ★7

Read all the reviews ›

Top questions

What exactly is Brunello di Montalcino, and why is it tasted in the wineries instead of somewhere else?

Brunello di Montalcino is a red wine made exclusively from Sangiovese grapes grown in the hills around Montalcino, in Tuscany. The tastings happen at the estates where the wine is made and aged, so you taste it in the cellars and tasting rooms where the winemakers themselves work — that's where the wine lives for years before it leaves the region.

How much walking and climbing is involved in this tour?

A moderate amount of stairs and walking is involved. You'll walk through the wineries during tastings, climb and descend stairs in the estates, and have free time to explore Montalcino on foot — the medieval town is built on a hill, so the streets have slopes and steps. The fortress at the top is optional during your free time.

What's included in the Tuscan snack between tastings?

The snack is traditional and simple: fresh local bread and extra virgin olive oil. It's served between the two wine tastings and gives you a chance to sit and absorb what you've tasted before moving to the next winery.

Can I visit the Montalcino Fortress during the free time, or is it part of the guided tour?

The fortress is in Montalcino, where you have free time after the tastings. You can visit it on your own during that window — the guide can tell you how to reach it — but it's not a guided stop. Many people walk up to it for the views across the Val d'Orcia vineyards.

What language is the guide, and will I understand the wine tastings if I don't speak Italian?

The guide speaks English, Spanish or Italian depending on the group composition. During the tastings, the guide provides translation support when needed, so you'll understand what the winemakers or estate staff are explaining about the wines and the winemaking process.

How many people are on this tour, and will it feel crowded?

Groups are small: a maximum of eight people travel in a minivan, or up to thirty in a minibus if the tour runs as a larger group. The smaller minivan groups tend to feel more intimate, especially during the tastings at the estates.