Tuscan Hills Full-Day Tour: Val d'Orcia, Montalcino, Montepulciano & Pienza with 2 Wine & Cheese Tastings
A journey through rolling hills, Renaissance towns, and the legendary wines of southern Tuscany.
This Tuscan Hills full-day tour takes you deep into the Val d'Orcia, a UNESCO World Heritage landscape, visiting three of the region's most celebrated hilltop towns in a single immersive day. Two dedicated wine and pecorino cheese tastings give you direct access to flavors that have defined this territory for centuries.
The route connects Pienza, Montalcino, and Montepulciano — each town distinct in character yet sharing the same golden-hued stone, medieval roots, and commanding views over cypress-lined valleys. Between stops, the road winds through some of the most photographed countryside in Italy, offering continuous visual rewards for anyone with a camera or a curiosity for landscapes.
The day is paced to allow genuine exploration rather than a rushed overview. Free time in each town lets you browse local markets, climb to a fortress wall, or simply sit with a coffee in a sun-warmed piazza and absorb the atmosphere that writers and filmmakers have drawn on for generations.
Underground cellars, an interactive wine museum, and a gourmet lunch paired with regional wines round out an itinerary designed to engage all the senses. This tour suits travelers who want substance alongside scenery — a full picture of what makes southern Tuscany one of Italy's most enduring destinations.
Tour Highlights
Explore the UNESCO-listed Val d'Orcia, one of Italy's most iconic protected landscapes.
Taste Brunello di Montalcino and Vino Nobile di Montepulciano alongside authentic local pecorino cheese.
Discover Pienza's Renaissance architecture, including the Duomo and Palazzo Piccolomini, designed for Pope Pius II.
Walk through Montalcino's medieval streets and visit its commanding fortress overlooking the valley.
Step inside the Temple of Brunello, an immersive multi-sensory museum housed in a former Augustinian convent.
Visit Montepulciano's historic underground cellar, a setting as dramatic as the wines produced within it.
Photograph cypress avenues, olive groves, and sculpted vineyard rows across the Orcia valley floor.
Itinerary
The tour departs from Florence in the morning, heading south through the Sienese hills toward the Val d'Orcia. The drive itself offers an introduction to the Tuscan landscape before the first stop is reached.
Approximately ninety minutes from Florence, Pienza greets visitors with Piazza Pio II, its honey-colored buildings, the Duomo of Santa Maria Assunta, and Palazzo Piccolomini — a palace that appeared in Zeffirelli's adaptation of Romeo and Juliet. Free time allows you to walk the perimeter walls and take in the sweeping panorama of the Val d'Orcia below.
The route continues to Montalcino, birthplace of Brunello wine, where steep alleys and a massive 14th-century fortress define the townscape. After free time to explore and a coffee break in Piazza del Popolo, the group enters the Temple of Brunello inside the former convent of Sant'Agostino — an interactive museum tracing the history and production of one of Italy's most celebrated red wines.
In the convent's cloister, a curated lunch of gourmet Tuscan dishes is served alongside three glasses of local wine selected to complement the flavors of the region. The setting — an ancient courtyard — adds a distinctive character to the meal.
The final town on the itinerary, Montepulciano is known for its Vino Nobile vineyards and its layered Renaissance architecture. The visit concludes with a wine and pecorino cheese tasting inside one of the town's historic underground cellars before the group begins the return journey to Florence.
The tour heads back north, arriving in Florence in the early evening. The return drive follows the same scenic corridor through the Tuscan hills that opened the day.
What's Included
Included
- Professional licensed guide throughout the tour
- Comfortable air-conditioned transport from Florence
- Entry to the Temple of Brunello interactive museum in Montalcino
- Gourmet lunch with three glasses of paired local wine in Montalcino
- Wine and pecorino cheese tasting in Montalcino
- Wine and pecorino cheese tasting in Montepulciano's underground cellar
- Free time to explore Pienza, Montalcino, and Montepulciano independently
Not Included
- Personal travel insurance
- Additional food and beverages beyond those specified
- Entry fees to optional attractions not listed in the itinerary
- Gratuities for guide and driver (discretionary)
- Hotel pickup and drop-off (meeting point required)
Important Information
Ready to Explore the Heart of Tuscany?
Secure your place on this full-day journey through Val d'Orcia, Montalcino, Pienza, and Montepulciano — complete with tastings, history, and landscapes that stay with you long after the day ends.
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