Siena: Pienza & Montepulciano Day Trip with Farm Lunch

Two Renaissance Towns & a Tuscan Farm Lunch, South of Siena

From Siena you travel south through the clay hills of the Crete Senesi to Pienza, a Renaissance town designed on paper by architects for Pope Pius II. After exploring the town and its cathedral, you head to a local farm for lunch with wine and a lesson in pecorino cheese-making. The afternoon takes you to Montepulciano, where you taste Vino Nobile in a winery carved underground, then have free time to walk the town before returning to Siena. The small group keeps the pace relaxed, and the guide can answer questions.

Step-by-step itinerary

Stops and time spent at each

1. Basilica of San Domenicopassing by
2. Pienza1h
3. Val d'Orcia1h

Explore Pienza and Montepulciano

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

The experience

The day starts in Siena, where you meet your guide and climb into the minivan. You settle into the air-conditioned van, and as soon as you leave Siena's edges, the landscape shifts. The road south opens onto the Crete Senesi, those bare clay hills that look like someone erased the trees and left only the folds. Your guide points out a medieval hamlet tucked into the creases, explains why the earth looks that way, and you realize you're not on a standard Siena day trip anymore. This is the Val d'Orcia, a UNESCO site that actually looks like the postcards, not because it's been staged, but because it's been left alone.

Pienza arrives around midday. It's smaller than you expected, and that's the point. Pope Pius II had architects plan the whole thing on paper in the 1400s, renovating his native town into a Renaissance ideal. You walk the main square, peek into the cathedral, and there's time to wander the side streets without feeling rushed. The guide mentions the Romanesque church of Corsignano, but mostly leaves you to it. Some people take the scenic walk overlooking the hills. Others just sit on a bench and look at the valley. Then you're back in the van heading to the farm for lunch, and this is where the day settles into something real. The farm sits on a terrace overlooking the Val d'Orcia. Lunch is simple, built mostly on fresh ingredients from the farm, with a glass of local wine. Someone asks about the sheep, and the farmer walks you through the cheese-making process. You taste the Vino Nobile later in Montepulciano, but this lunch is the one you remember.

Montepulciano sits on a steep hill, and the climb up the main street is steeper than it looks. Your guide leads you to Piazza Grande, the main square, and points out the architecture. You can see Siena's medieval influence and Florence's Renaissance one, layered into the same buildings. Then there's a winery carved into the ground below the city, cool and dark, where you taste the Vino Nobile di Montepulciano. The wine is good, and the guide explains which families made it centuries ago. After that, you have free time. Some people visit churches or palaces. Others sit in a café. The guide mentions the Bravio delle Botti, a wild festival where neighborhoods race wine barrels up the hill, and you can almost picture it. Then it's the drive back to Siena. You're tired, your legs ache a little from the walking, and you're already thinking about booking another day trip.

What’s included

Your day includes transport in an air-conditioned minivan for up to 8 passengers, lunch on a local farm with wine and a lesson in cheese-making, a tasting of Vino Nobile at a winery in Montepulciano, and a guide who leads you through Pienza and Montepulciano with time for independent exploration in both towns.

Before you book

Days and timesMonday, Thursday, Friday and SaturdayDeparts at 09:30Last departure this season: 21 Dec

Book up toStart time

AgesAdult (3 and older) · Infant (under 3): free

GroupUp to 8

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated 2 days ago

Good to know

Low physical effortStroller-friendlyInfant seats availablePublic transport nearbyNot recommended with heart problems

Operated by Tuscan Escapes by Papilio SRL

Is this one for you?Book this if you want to see two of Tuscany's most distinctive towns and the Val d'Orcia landscape without renting a car or planning the route yourself: the small group size and fixed itinerary mean you spend the day looking around instead of navigating.

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Top questions

Can children come?

Yes. Ticket types: Infant (under 3): free.

Is lunch included, and what about wine?

Yes. Lunch is served on a local farm and includes fresh ingredients produced there, along with wine. If you're under 18, you won't be served alcohol.

Do I need to be fit or athletic for this tour?

The tour is suitable for all fitness levels. There is walking through the towns, including some uphill sections in Montepulciano, but the pace is leisurely and you have free time to rest.

What is included in the price?

Transport by air-conditioned minivan, lunch on the farm with wine, a winery tasting in Montepulciano, and a guide for the full day.

Will we visit both Pienza and Montepulciano?

Yes. You spend the late morning in Pienza, have lunch at a farm in the Val d'Orcia, and visit Montepulciano in the afternoon.

What if the weather is bad?

Farm lunch is served on a panoramic terrace weather permitting.

Can the itinerary change?

The itinerary may vary slightly on some days, but the tour keeps a similar overall plan, the same duration, and all the same inclusions.