Pienza & Montepulciano: Small-Group Day Trip from Siena with Farm Lunch

Summary

Winding roads, hill towns and farm tables in Val d’Orcia

You’ll ride out from Siena through clay hills into Val d’Orcia, wander Renaissance streets in Pienza, taste sheep cheese on a family farm with lunch overlooking the valley, then sip Vino Nobile inside Montepulciano’s ancient cellars—all with a small group and local guide who brings Tuscany alive in unexpected ways.

What’s the experience like?

Hands gripping my coffee cup, I watched our guide—Francesca, I think?—wave us over by the old stone steps outside San Domenico in Siena. She had this easy way of making you feel like you’d known her for ages. We piled into the minivan (eight of us, tops), and pretty soon we were winding out of town, the Crete Senesi rolling past like some kind of lunar painting. Someone cracked a window and there was that early Tuscan smell—earthy, a bit sharp, almost like hay after rain. We stopped for photos but honestly, I just stood there squinting at the hills because it didn’t look real.

Pienza came up quietly—a town that feels like it was drawn by someone who really loved symmetry. Francesca told us about Pope Pius II and how he wanted his hometown to be “perfect.” I tried to imagine what it was like back then but got distracted by the smell coming from a shop selling pecorino cheese. The streets are narrow and sun-warmed; you can hear your own footsteps echoing off the stones. I bought a tiny wedge of cheese (couldn’t resist) and wandered past little shops with hand-painted ceramics. There was this moment on the overlook where everyone just sort of went quiet—except for one guy’s camera shutter clicking away—and all you could see were hills stacked up into blue haze.

Lunch happened at a farm perched above the valley. They served us plates piled with things I couldn’t pronounce (Francesca tried to teach me but gave up laughing), plus fresh bread and their own wine. The sheep wandered close enough that you could hear them munching grass if you listened between conversations. I’m not sure what made it so good—the food or just sitting there in that light—but I still think about it sometimes when I’m stuck in traffic back home.

Montepulciano was last—a bigger hill town with steep lanes that made my legs ache in a good way. We ducked into an old winery carved right under the city; cool air, barrels everywhere, and that deep smell of oak and something sweet underneath. Tasted Vino Nobile (I pretended to know what I was doing swirling it). Francesca explained how they roll barrels uphill during their festival—sounds impossible but apparently they do it every year. After wandering through stone alleys and catching bits of local chatter, we headed back as the sky started turning gold over Val d’Orcia. Kind of hard to leave when your shoes are dusty and your head’s full of new names and flavors.

Step-by-step itinerary

Day 1 — Explore Tuscany's Val d’Orcia region

• Meet guide at San Domenico church
• Travel south through Crete Senesi
• Stop for photos at Crete Senesi
• Visit medieval hamlet
• Arrive in Pienza town
• Explore Pienza cathedral and streets
• Lunch at Val d'Orcia dairy farm
• Visit Montepulciano hill town
• Tour Piazza Grande and winery
• Enjoy free time in Montepulciano

Top questions

How long is the day trip from Siena to Montepulciano & Pienza?

The tour lasts approximately one full day, starting at 9:30am in Siena.

Is lunch included on this Montepulciano & Pienza tour?

Yes, lunch is included at a local dairy farm featuring fresh regional ingredients and wine.

How many people are on this small-group tour?

The group size is limited to 8 travelers for a more personal experience.

Does the tour include wine tasting in Montepulciano?

Yes, you'll visit an old winery in Montepulciano for Vino Nobile tastings.

Where does the tour start?

The meeting point is in front of San Domenico church in Siena at 9:30am.

Are infants or children allowed on this day trip?

Yes, infants and small children can join; infant seats are available upon request.

Do we visit any UNESCO sites during this tour?

Yes, you'll travel through Val d'Orcia, which is recognized as a UNESCO World Heritage site.

What’s included

Your day includes pickup from Siena at San Domenico church, comfortable minivan transport for up to eight guests, guidance from a knowledgeable local throughout Val d'Orcia’s landscapes and towns, entry to an old winery with tastings in Montepulciano, plus a generous farm lunch with regional wine—all before returning to Siena as evening falls.