Val d'Orcia private tour: Montalcino, Pienza, Montepulciano
Ten hours in a private car through the villages, vineyards and cypress-lined roads that define Tuscany.
A private ten-hour tour of Val d'Orcia from Florence with your own driver, visiting Montalcino, Pienza, and Montepulciano at your own pace. You're picked up at your hotel and dropped back there after exploring each village's cobbled streets, wine shops, and Renaissance architecture, with photo stops at the Chapel of the Madonna di Vitaleta and the Gladiator filming location along the way.
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Step-by-step itinerary
Private tour through Val d'Orcia
- Pick up from Florence accommodation
- Drive through Tuscan countryside
- Explore Montalcino town and fortress
- Visit Chapel of Madonna di Vitaleta
- See Gladiator filming location
- Wander Pienza and taste Pecorino cheese
- Discover Montepulciano and wine enoteca
- Return to Florence accommodation
- Florence 2h
- Montalcino 2h
- Cappella Madonna di Vitaleta 30m
- Pienza 1h
- Montepulciano 2h
- Florence 2h
What’s included
- Your private driver for the full ten hours.
- hotel pickup and drop-off in Florence.
- a fully-fitted Mercedes with air conditioning, USB chargers, and free WiFi.
- bottled water.
- expert commentary on board.
- photo stops at the Chapel of the Madonna di Vitaleta and the Gladiator filming location.
- independent sightseeing in Montalcino, Pienza, and Montepulciano.
- and dedicated office support before, during, and after your tour.
- Every day 08:00 08:30 09:00
Information
Ten hours through Val d'Orcia's UNESCO villages with your own driver: Montalcino's Brunello wine quarter, Pienza's Renaissance streets.
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The experience
The drive from Florence takes around two hours through rolling hills and vineyards before you reach Montalcino, where you have an hour and a half to wander the medieval streets on your own. This is Brunello wine country: the town's wine shops and fortress overlook the Val d'Orcia's patchwork of vines and cypress trees. Your driver stays available if you want to move on early or linger longer. The itinerary bends to your pace, not the other way around.
Between Montalcino and Pienza, ask your driver to stop at the Chapel of the Madonna di Vitaleta, the most photographed landmark in Tuscany: a small stone chapel framed by cypress trees in an open valley, with no other building in sight. From there, the route passes through the golden wheat fields where Ridley Scott filmed Gladiator: the same gates and landscape where Maximus walks toward his home. Most travelers spend thirty minutes at each stop, though you're free to stay as long as you want.
Pienza sits on a hilltop and was rebuilt in the fifteenth century as Pope Pius II's vision of an ideal Renaissance city, which means its streets follow a plan for beauty and balance rather than the organic tangle of older towns. You have an hour and a half there to browse the stone alleyways and taste Pienza's famous Pecorino cheese. Your final stop is Montepulciano, another hilltop village known for Vino Nobile and Renaissance palaces, where you get the same hour and a half to explore wine enotecas, admire the architecture, or pick up souvenirs before your driver takes you back to Florence.
Top questions
What languages is the tour guided in?
Live guide in English, Spanish and Italian.
How much time do I spend driving versus exploring the villages?
The drive from Florence to Val d'Orcia takes around two hours each way. You get an hour and a half in each of the three main towns (Montalcino, Pienza, and Montepulciano) plus thirty minutes at each of the two photo stops, the Chapel of the Madonna di Vitaleta and the Gladiator filming location. Your driver stays with the car and is available whenever you're ready to move on.
Can I customize which villages I visit or how long I spend in each one?
Yes. The itinerary is flexible, and you can ask your driver to adjust the stops or the time spent at each location. You can also add optional services like a wine tasting at checkout, which changes how the day unfolds.
What is the Chapel of the Madonna di Vitaleta, and why do so many people photograph it?
The Chapel of the Madonna di Vitaleta is a small stone chapel in the middle of Val d'Orcia's rolling hills, surrounded by cypress trees and open fields with no other buildings nearby. Local legend says the Virgin Mary appeared to shepherds there. It's one of Tuscany's most iconic views and sits perfectly framed for photographs, which is why it appears on postcards and in travel guides across the region.
What can I expect to see and do in Montalcino?
Montalcino is a medieval hilltop town surrounded by vineyards and known worldwide for Brunello wine. You'll walk through cobblestone streets lined with wine shops, artisanal boutiques, and Romanesque churches. The fortress at the top of town offers sweeping views over the Val d'Orcia's countryside of vineyards, cypress trees, and country roads. You have an hour and a half to explore on your own.
Is Montepulciano worth visiting if I'm not interested in wine?
Montepulciano is worth visiting for its Renaissance architecture and hilltop setting alone. The town has grand churches, elegant palaces, and sweeping views over the Tuscan countryside. It was also used as a filming location for the New Moon vampire film. You have an hour and a half to stroll the atmospheric streets, admire the buildings, and browse artisanal shops for souvenirs.
What's included in the tour, and what do I need to pay for separately?
Your ten-hour tour includes hotel pickup and drop-off, a private driver in a Mercedes with air conditioning and WiFi, bottled water, and independent time to explore each village at your own pace. Wine tastings are optional and available on some tour options at checkout. Meals and gratuities are not included.
Operated by Ciao Florence Tours Srl. Explorevia does not run this tour: we compare it with similar options, and you book it with our booking partner.
Prices and times updated 5 days ago
Val d'Orcia private tour: Montalcino, Pienza, Montepulciano
10h · EN · ES · IT · at your hotel
from € 545 per person
≈ US$ 612 in your currency
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