Brunello Wine Tour from Siena with Montalcino Visit

Sample various reds across two vineyards and wander medieval village streets with an expert guide

Travel Flexibly
· 5h · Siena, Italy

Taste the heritage of Brunello di Montalcino, one of the most strictly regulated wines in the world. Leave Siena behind and head to Tuscany's vine-covered hills to Montalcino, where Sangiovese grapes transform into Italy's most prized wine. Step inside two prestigious cellars to taste Brunello aged in oak barrels, eat olive oil and bread, and hear how generations of winemakers have perfected this craft. Between tastings, explore Montalcino's medieval fortress and charming lanes at your own pace.

What You Get With This Tour

  • Expert English-speaking guide
  • Round-trip minivan transport from Siena
  • Brunello tastings at two wineries
  • Free time in Montalcino
  • Scenic Tuscan countryside drive
  • Uncork the magic of the Val d'Orcia
  • Guide tips
  • Meals

Tour Itinerary

  • 1

    Meet your guide at Stazione di Siena

    Your adventure begins at the Siena train station, where you'll meet your expert guide and board a comfortable minivan. As you leave the city walls behind, watch the landscape shift into the iconic cypress-lined roads and rolling golden hills of the Val d'Orcia region.
  • 2

    Visit a prestigious wine estate

    Arrive at a historic winery to see where the famous Sangiovese grapes grow under the Tuscan sun. You will head underground into the cool cellar to see the massive oak barrels where the wine rests for years before tasting several bold, structured vintages with your guide.
  • 3

    Sample local olive oil

    Take a break from the wine to appreciate Tuscany's other liquid gold during a guided olive oil tasting. You'll drizzle extra virgin oil over crusty bread and learn why the soil in this specific region produces such a distinctive, peppery finish that local families have loved for centuries.
  • 4

    Taste vintages at a second winery

    Continue your education at a different estate to compare winemaking styles and family traditions. By tasting a second flight of Brunello, you will notice how different elevations and soil types create unique flavors, helping you identify your own personal preferences in every glass.
  • 5

    Explore the village of Montalcino

    Head into the heart of Montalcino for some independent exploration of this medieval hilltop sanctuary. You can climb the stairs of the 14th-century fortress for a bird’s-eye view of the vineyards, shop for local leather goods, or enjoy an espresso in the quiet central piazza.
  • 6

    Finish your tour in Siena

    Relax on the scenic drive back through the countryside as the afternoon light hits the hills. Your tour concludes back at the Siena train station, where your guide can provide excellent dinner recommendations or directions to your next destination while you enjoy a savory souvenir.

Additional Information

Discover what to expect, what’s included, and everything you need to know before booking. 

Good to know:

  • Accessibility: This tour involves walking and climbing stairs at vineyards and cellar sites. It is unfortunately not wheelchair accessible.

  • Alcohol Consumption: Wine tastings are included throughout the tour. Participants consuming alcohol must be of legal drinking age in Italy (18). Please bring a government-issued ID if you plan to partake.

  • Minimum Participants: During the winter season, a minimum of four people is required to activate the tour. If the minimum is not reached, you will be offered an alternative date or a full refund.

  • Check-in: Arrive 15 minutes early for check-in at the meeting point so the group can depart on time.

Your 5-hour tour includes:

  • Expert English-speaking guide

  • Round-trip transport in air-conditioned minivan

  • Wine tastings at two prestigious Brunello wineries

  • Olive oil and bread snack

  • Free time to explore Montalcino and its fortress

  • Scenic drive through Tuscany's rolling hills

What to bring:

  • Comfortable walking shoes

  • Government-issued ID

  • Water bottle

  • Camera

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Frequently Asked Questions

Is this tour family friendly?

Yes, children are welcome on this tour. However, the experience focuses on wine tastings, so it's best suited for adults. Participants must be 18 or older to drink alcohol.

What if I have concerns about my mobility on this tour?

This tour involves walking and climbing stairs at vineyards and cellar sites. Unfortunately, it's not wheelchair accessible. If you have mobility concerns, please contact us in advance.

How much wine will I taste?

You'll enjoy tastings at two prestigious Brunello wineries, with multiple wines sampled at each estate. The exact number of tastings may vary by winery.

Is lunch included?

Lunch is not included, but you'll enjoy olive oil and bread snacks during the tour. You're welcome to grab a bite during your free time in Montalcino.

What happens if it rains?

This tour runs rain or shine. The wine tastings take place indoors at the cellars, though you'll be outdoors during your free time in Montalcino.

Start From: $143.99

Available days Discounted days

Free cancellation up to 24 hours in advance!