Private Tuscany Wine Tour: Montepulciano and Siena from Florence
A full-day private journey through rolling hills, ancient cellars, and the finest wines of Tuscany
This private Tuscany wine tour delivers an unhurried, deeply personal experience through two of the region's most celebrated destinations. Traveling with a dedicated driver, guests move through the landscape at their own pace, far from the crowds of standard group excursions.
The route winds through the Crete Senesi, a stretch of clay hills whose pale ridges and isolated farmhouses define the visual character of southern Tuscany. This particular landscape, often overlooked by itinerary planners, sets the tone for a day rooted in place and tradition.
In Montepulciano, a visit to a working winery introduces guests to the production methods behind the area's flagship wine, accompanied by a tasting led by a resident winemaker. The afternoon continues in Siena, a UNESCO World Heritage city whose medieval streets and central piazza carry centuries of civic history.
The experience is suited to couples, families, and independent travelers who value privacy, authenticity, and the unhurried rhythm of a properly organized private day.
Tour Highlights
Taste Vino Nobile di Montepulciano DOCG directly at a working winery, guided by winemaker Alfredo.
Explore Etruscan and Roman wine cellars beneath the hilltop town of Montepulciano, some predating the common era.
Sample local specialties including cold cuts, pecorino, bruschetta, Vin Santo, and cantucci during the winery tasting.
Drive through the Crete Senesi, one of Tuscany's most distinctive and photogenic landscape corridors.
Visit Siena's Piazza del Campo, the site of the historic Palio horse race and a centerpiece of medieval Italian civic architecture.
Travel entirely in private with a dedicated driver, allowing a fully flexible and personalized daily rhythm.
Taste five organic wines and extra-virgin organic olive oil, including flavored varieties, directly from the producer.
Itinerary
Your private driver collects you from your accommodation in Florence and heads south toward Montepulciano. The route passes through the Crete Senesi, a landscape of pale clay hills that is characteristic of this part of Tuscany.
At a selected winery, winemaker Alfredo leads a guided tour of the summer cellars, covering organic production methods and the origins of each wine. The visit includes five organic wines, organic extra-virgin olive oil, and an explanation of how to evaluate each product.
The tasting session features Vino Nobile di Montepulciano alongside cold cuts, hams, cheeses, specialty olives, bruschetta, Vin Santo, and cantucci. Winemaker Alfredo presents each wine, explaining its character, production history, and regional significance.
After the winery, guests have time to walk the narrow streets of Montepulciano, a walled hilltop town at 605 meters above sea level with Etruscan and Roman cellars open for exploration. Lunch at a local restaurant specializing in traditional Tuscan recipes is available at personal expense.
The tour continues to Siena, a well-preserved medieval city whose historic center is listed as a UNESCO World Heritage Site. Guests explore Piazza del Campo, home to the Torre del Mangia and the site of the Palio, and have time to sample local products including pici, pappardelle, pecorino, and panforte.
Your private driver returns you to your accommodation in Florence, concluding the tour. The return journey follows a direct route through the Tuscan countryside.
What Is Included
Included
- Private driver and vehicle for the full day
- Guided cellar tour at a working winery in Montepulciano
- Tasting of five organic wines and organic extra-virgin olive oil
- Tasting of Vino Nobile di Montepulciano and Vin Santo
- Local food pairings: cold cuts, cheeses, bruschetta, cantucci, olives
- Personal presentation by winemaker Alfredo
- Guided time in Siena's historic center
Not Included
- Lunch at local restaurant
- Personal purchases at the winery or in town
- Gratuities for the driver or guide
- Travel insurance
- Entrance fees to optional monuments or museums
Important Information
Reserve Your Private Tuscany Day
Secure your private driver, winery access, and expert wine presentation for a full day in the Tuscan countryside. Availability is limited for private departures.
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