PRIVATE HILL TOWNS & VAL D’ORCIA EXPERIENCE
Explore Pienza, Montepulciano and the beautiful countryside of southern Tuscany with Fabrizio, your Local Tuscany Host.
Walk Renaissance streets, discover local food and wine traditions, enjoy panoramic views across Val d’Orcia and experience both towns without the rushed pace of a large group tour.
100% Private | Approx. 4 Hours | Personally Hosted | €400 for Two Guests
Only you and your travel companions.
Experience both Pienza and Montepulciano.
Enjoy some of southern Tuscany’s most iconic landscapes.
Experience southern Tuscany at a relaxed, flexible pace.
TWO TOWNS THAT BELONG TOGETHER
Pienza and Montepulciano offer two very different sides of southern Tuscany, yet they sit close enough to enjoy together without spending your day driving from place to place.
Pienza is graceful, compact and surrounded by the landscapes of Val d’Orcia. Montepulciano is larger and more dramatic, rising above vineyards and countryside with steep historic streets and centuries of wine tradition.
Between the two, the drive itself becomes part of the experience — rolling farmland, cypress trees, vineyards and views that many travelers picture when they imagine Tuscany.
Because your experience is private, we can slow down where you want to, skip what doesn’t interest you and make the day feel personal rather than like a checklist.
PIENZA
Pienza may be small, but it tells a remarkable story. Pope Pius II transformed his birthplace during the Renaissance into what was intended to be an ideal city — harmonious, elegant and designed around human scale.
We’ll explore Piazza Pio II and the surrounding historic streets before walking toward panoramic viewpoints overlooking Val d’Orcia.
Pienza is also closely connected to one of Tuscany’s best-known foods: Pecorino di Pienza. You’ll see local shops filled with wheels of sheep’s-milk cheese and learn why shepherding and cheese-making remain such an important part of the area’s identity.
There is time to enjoy the town rather than simply walk through it — whether that means photos, browsing a shop, stopping for coffee or simply enjoying the view.
BETWEEN THE HILL TOWNS
The road between Pienza and Montepulciano takes us through some of southern Tuscany’s most memorable countryside.
Val d’Orcia is known for its rolling farmland, cypress-lined roads, hilltop farms and broad views that change with the seasons — green in spring, golden during summer and warmer and softer as autumn arrives.
Because this is a private experience, scenic stops don’t have to be predetermined. If we find a view you’re especially enjoying, we can stop, take photographs and simply spend a little time there.
That flexibility is one of the biggest differences between experiencing Val d’Orcia privately and seeing it from the window of a large tour bus.
MONTEPULCIANO
Montepulciano rises dramatically above the surrounding countryside, with long historic streets climbing toward Piazza Grande at the top of town.
As we explore, you’ll pass Renaissance buildings, artisan shops, cafés and centuries-old spaces that tell the story of one of southern Tuscany’s most important hill towns.
Wine is also woven deeply into Montepulciano’s identity. The town is famous for Vino Nobile di Montepulciano, and its historic center contains remarkable underground wine cellars carved beneath centuries-old buildings.
Depending on your interests and available time, we can stop to see one of these historic cellars and learn more about the wine tradition that has shaped the town.
The upper parts of Montepulciano also offer beautiful views over the vineyards and countryside — especially rewarding after the walk uphill.
AN UNHURRIED HALF-DAY EXPERIENCE
The order can change depending on your starting point, timing and interests, but a typical experience might include:
Walk Piazza Pio II, Renaissance streets and panoramic viewpoints while discovering the town’s history and Pecorino tradition.
Travel through countryside, vineyards and scenic roads with time for photographs and spontaneous stops.
Explore the historic center, Piazza Grande, local shops, viewpoints and Montepulciano’s centuries-old wine culture.
TURN YOUR TOUR INTO A LONGER TUSCAN DAY
If you’d like to spend more time enjoying the countryside, you can add one of two authentic farm-based lunch experiences to your private tour.
Both options connect the landscape you’re seeing with the people and food traditions of southern Tuscany.
Each lunch option is €60 per person and is subject to availability.
PRIVATE PIENZA & MONTEPULCIANO TOUR
Approximately 4 hours · Fully private
Fabrizio personally plans the route, timing and transportation so you can enjoy both towns and the countryside without worrying about logistics.
✓ Private transportation
✓ Personally hosted by Fabrizio
✓ Time to experience Pienza
✓ Time to experience Montepulciano
✓ Val d’Orcia countryside drive
✓ Flexible scenic and photography stops
✓ Tour planning and local logistics
Additional guest pricing is available upon request. Optional lunches are €60 per person.
Check Availability for Your DateIS THIS THE RIGHT TUSCANY EXPERIENCE FOR YOU?
See two essential southern Tuscan hill towns without trying to navigate or plan the route yourself.
Discover Renaissance Pienza and Montepulciano’s centuries of architecture and local tradition.
Enjoy hill-town streets, panoramic viewpoints and the landscapes of Val d’Orcia at a flexible pace.
Add a farm lunch or explore the Pecorino and wine traditions closely connected to these towns.
WANT A DIFFERENT KIND OF DAY?
Spend more of your day visiting family-owned wineries, vineyards and tasting rooms throughout southern Tuscany.
Explore Private Wine ToursCombine towns, food, wine, countryside and local experiences in an itinerary built specifically around you.
Create a Custom TourChoose Fabrizio’s signature full-day experience if you want hill towns, wine, countryside, food and dinner at his Montepulciano home.
Explore the Ultimate TourPLANNING YOUR PRIVATE TOUR
Have a question about your dates or itinerary? Ask Fabrizio directly.
Yes. The experience is completely private for you and your travel companions and is personally hosted by Fabrizio.
The standard tour lasts approximately four hours, including transportation between the towns and time to enjoy the surrounding countryside.
The private tour costs €400 for two guests. Pricing for additional guests is available upon request. Optional lunch experiences are €60 per person.
Yes. Pienza sits within Val d’Orcia, and the countryside between Pienza and Montepulciano is an important part of the experience. Depending on your route and interests, Fabrizio can include scenic stops and viewpoints along the way.
Yes. Depending on availability, you can add either a farmhouse lunch with olive oil tasting or a sheep farm and artisan cheese lunch. Both options cost €60 per person.
No. The sheep farm experience includes a visit to the farm and a charcuterie-style lunch with homemade cheeses and fresh ricotta. You’ll learn about the farm and its cheese traditions, but it is not a hands-on cheese-making class.
A formal winery tasting is not included in the standard four-hour tour. Montepulciano’s historic wine culture is part of the experience, and depending on timing you may visit a historic cellar. For a dedicated winery experience, consider Fabrizio’s Private Tuscany Wine Tour.
Pickup and drop-off are available from eligible accommodations around Montepulciano, Pienza and the surrounding Val d’Orcia area. Fabrizio can confirm transportation details when you submit your request.
Both towns are explored primarily on foot. Montepulciano is built on a hill and includes sloping streets, so comfortable walking shoes are recommended. Fabrizio can adjust the pace to suit your group.
Yes. Because the experience is private, Fabrizio can adjust the pace and emphasis based on your interests. For a more extensively customized itinerary involving additional towns, wineries or activities, consider a Custom Tuscany Tour.
TWO HILL TOWNS. THE COUNTRYSIDE BETWEEN THEM. YOUR OWN PRIVATE DAY.
Tell Fabrizio when you’ll be in Tuscany, where you’re staying and who’s traveling with you. He’ll take care of the route and help you create a relaxed day in southern Tuscany.
