Siena, Cortona, Montepulciano and Val d'Orcia Small Group Tour
Journey through the hilltop towns and cinematic landscapes that have defined Tuscany on the world stage.
This Tuscany small group day tour takes you through four of the region's most celebrated destinations — Cortona, Montepulciano, the Val d'Orcia, and Siena — aboard a comfortable eight-seat minivan with a passionate local guide. The intimate group format allows for genuine conversation, personal stops, and a pace that feels nothing like a standard bus tour.
Tuscany has long captivated filmmakers, novelists, and travelers in equal measure. The towns visited on this itinerary have appeared in productions including Under the Tuscan Sun, Twilight Saga: New Moon, Letters to Juliet, The English Patient, and A Midsummer Night's Dream, giving each destination a layer of cultural resonance that extends well beyond their medieval walls.
Between town visits, guests stop at a working Tuscan farm to sample house-cured meats, bruschetta, and estate wine. A second tasting takes place in a fourteenth-century underground cellar in Montepulciano, where the celebrated Vino Nobile DOCG is poured for complimentary enjoyment. The day ends with an evening stroll through Siena before the return drive to Florence.
Tour Highlights
Walk the streets of Cortona, Montepulciano, and Siena made famous by major international films and celebrated literary works set in the Tuscan countryside.
Enjoy a farm tasting board featuring Cinta Senese cured meats and bruschetta made with garden-fresh ingredients, paired with estate-produced wine among olive trees and vineyards.
Descend into a fourteenth-century underground cellar in Montepulciano for a complimentary tasting of Vino Nobile di Montepulciano DOCG, one of Italy's most respected red wines.
Travel through the Val d'Orcia UNESCO landscape, admiring the rolling hills, terraced farmland, and cypress-lined roads that have defined the Tuscan visual identity for centuries.
Explore each town independently with free time built into every stop, giving guests the freedom to browse artisan shops, photograph landmarks, or simply sit in a medieval piazza.
Travel in a private eight-seat minivan with a knowledgeable local guide whose commentary connects each location's history, film appearances, and regional character throughout the day.
Itinerary
The group assembles at Porta Romana in central Florence and departs by minivan into the Tuscan countryside. After approximately ninety minutes, the vehicle arrives in Cortona, the hilltop town immortalized by Diane Lane in Under the Tuscan Sun. Guests explore independently, wandering narrow streets lined with artisan workshops and taking in panoramic views over the valley below.
A forty-minute drive from Cortona leads to a working farm in the heart of Tuscany where Cinta Senese pigs roam semi-wild among olive groves and vineyards. Guests enjoy a tasting board of house-cured meats and fresh bruschetta, paired with the farm's own wine. The setting and the produce together offer an authentic glimpse into the agricultural traditions that underpin Tuscan cuisine.
The itinerary continues to the walled town of Montepulciano, recognizable to fans of the Twilight Saga: New Moon and home to the prized Vino Nobile DOCG appellation. The guide shares context about the town's film history and architectural heritage during the drive. Near the village entrance, guests descend into a fourteenth-century cellar for a complimentary wine tasting before exploring the town at their own pace.
After Montepulciano, the minivan passes through the Val d'Orcia, a UNESCO World Heritage landscape known for its softly contoured hills, geometric crop patterns, and rows of cypress trees. The drive is unhurried, allowing guests to absorb the scenery that has featured in films such as The English Patient and Letters to Juliet. This portion of the day serves as a natural pause between the town visits.
The final stop is Siena, the medieval city whose striped cathedral and shell-shaped Piazza del Campo have drawn visitors for centuries. The guide escorts guests from the parking area to the main square before allowing approximately one hour of free time to explore independently. The group then returns to Florence, arriving in the early evening.
What Is Included
Included
- Private eight-seat minivan transport throughout the day
- Local driving guide with English-language commentary
- Farm tasting board with cured meats, bruschetta, and estate wine
- Complimentary Vino Nobile DOCG tasting in Montepulciano cellar
- Guided escort into the center of each town
- All transport between stops on the itinerary
Not Included
- Lunch and additional meals beyond the included tastings
- Entrance fees to museums or paid attractions at individual stops
- Personal travel insurance
- Gratuities for the guide
- Any items of a personal nature purchased during free time
Important Information
Reserve Your Place on This Tour
Spaces are limited to eight guests per departure, making early booking advisable, particularly during spring and summer. Secure your seat today and experience Tuscany's most celebrated towns with a guide who genuinely knows and loves the region.
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