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A full-day journey combining towns, landscapes, wine, and local culture — guided personally by Fabrizio.
Private Tour of Pienza and Montepulciano with a Local Guide
Explore Pienza and Montepulciano at a Relaxed, Local Pace
This is a half-day private tour of Pienza and Montepulciano, guided by me, Fabrizio. We explore Pienza and Montepulciano on foot, with time for views, history, local food, and quiet corners most group tours rush past.
This tour is ideal for couples and small groups who want a flexible, unhurried way to experience Tuscany’s towns — with the option to extend the day into a wine experience or countryside lunch.
Walking Through Pienza, the “Ideal City”
Pienza was redesigned during the Renaissance as a model town, and its layout still feels open, calm, and easy to explore on foot.
We walk through the main square, Piazza Pio II, and along panoramic streets that overlook the Val d’Orcia countryside. Along the way, I’ll share the history behind the town’s design and point out small food shops where you can sample Pecorino di Pienza, the local cheese the town is famous for.
This part of the tour is relaxed and flexible, with time to stop for photos, coffee, or small tastings depending on what interests you most.
Exploring Montepulciano’s Hilltop Streets and Wine Cellars
Montepulciano sits high above the surrounding vineyards, with long, sloping streets that lead up to Piazza Grande, the heart of the town.
As we walk, you’ll pass historic buildings, artisan shops, and traditional cafés. If you’d like, we can stop in one of the town’s underground wine cellars to taste Vino Nobile di Montepulciano, one of Tuscany’s most well-known wines.
From the upper viewpoints, you’ll have wide views across the countryside — a favorite spot for travelers who enjoy photography and quieter moments away from busy squares.
If you’d like to turn the afternoon into a full wine-focused day, many guests continue with my Private Wine Tour in Tuscany, visiting family-owned wineries in the Val d’Orcia countryside.
For travelers who want to combine towns, wine, landscapes, and food into one complete experience, my Fabrizio’s Ultimate Tuscan Tour offers a full-day journey through the heart of Tuscany.
Private Tour of Pienza and Montepulciano – Pricing & Inclusions
Duration: Approximately 4 hours
I handle transportation, timing, and reservations so you can focus entirely on enjoying the day.
What’s Included in Your Exclusive Experience:
This private 4-hour tour is designed to give you a meaningful, relaxed introduction to both towns without feeling rushed. I handle the route, timing, and local logistics, so you can focus on exploring, tasting, and enjoying the day.
Enhance your experience with optional add-ons:
- Combine with a winery visit for a full-day experience
- Private Chef Lunch & Olive Oil Tasting (€95 per person)
- Private Dinner in my home after your tour
Frequently Asked Questions About Touring Pienza & Montepulciano
Here are a few common questions travelers ask before booking tour. If you have something specific in mind, please feel free to contact me here.
Is this tour private?
Yes. This is a fully private tour for you and your group, guided personally by Fabrizio.
How long is the Pienza and Montepulciano tour?
The experience lasts approximately 4 hours, with flexible timing based on your pace and interests.
Can I add a wine tasting or lunch?
Yes. You can extend the tour with a winery visit, countryside lunch, or private dinner in Montepulciano.
Where does the tour start and end?
Pickup and drop-off are available from accommodations in or near the Montepulciano and Val d’Orcia area.
