Private Montalcino and Pienza Tour from Siena: Val d'Orcia

Drive the Val d'Orcia's most photographed route, stopping to taste Pecorino and wine

A private tour from Siena through the Val d'Orcia UNESCO World Heritage landscape to Montalcino and Pienza, with an hour to explore each hilltop town. You taste Pecorino cheese in a traditional Pienza bottega, visit a winery, and enjoy a Tuscan lunch with wine. Hotel pickup and drop-off from Siena are included.

Step-by-step itinerary

Stops and time spent at each

1. Montalcino1h
2. Pienza1h · entry included

Explore Montalcino and Pienza in Tuscany

• Travel from Siena to Montalcino
• Free time to stroll and shop in Montalcino
• Visit Brunello di Montalcino wine cellars
• Travel to Pienza
• Stroll narrow streets of Pienza
• Enjoy cheese tasting in Pienza
• Return to Siena

The experience

Montalcino sits high above the Val d'Orcia, surrounded by the vineyards that produce Brunello di Montalcino. The tour gives you an hour to walk the narrow streets, shop, or simply stand in the town and absorb it: the landscape rolls out below in every direction. From there, the route crosses the valley floor to Pienza, the Renaissance town built to a single architectural vision, where you get another hour to wander and grab an ice cream if you want one.

The cheese tasting happens in a traditional bottega in Pienza, where you taste Pecorino di Pienza, the local sheep's milk cheese. Afterward, the tour takes you to a winery in the Brunello region for a tasting and a look at the cellars. Lunch is Tuscan. The operator does not specify the exact menu, but wine comes with it. Hotel pickup and drop-off from Siena bookend the day, so you do not arrange transport yourself.

The tour runs six hours total and travels as a private group, meaning no strangers on the bus and no fixed departure time. You choose when to start. Your guide speaks English, Spanish or Italian, depending on which you request at booking. Children from age three are welcome.

What’s included

• Hotel pickup and drop-off from Siena.
• one hour of free time in Montalcino.
• one hour of free time in Pienza.
• cheese tasting in a traditional Pienza bottega.
• winery visit with cellar tour and wine tasting.
• Tuscan lunch with wine.
• live guide in English, Spanish or Italian.

Before you book

Days and timesEvery dayDeparts at 09:30

Book up to1d before

AgesAdult (18 and older) · Youth (12 to 17 years) · Child (3 to 11 years) · Under 3: can't be booked

GroupPrivate

Live guideEnglish, Spanish and Italian

Meeting point and pickupHotel pickup is optional; you can also go straight to the meeting point. Ends back at the starting point.You can choose from 20 pickup points.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

Prices and times updated 2 days ago

Good to know

Low physical effortStroller-friendlyInfant seats availablePets welcomePublic transport nearby

Operated by Tuscany Private Tour

Is this one for you?Book this tour if you want to see the Val d'Orcia's most famous stretch without driving yourself or joining a group with strangers. The private format means your guide adjusts the pace to your interests, and hotel pickup eliminates the need to navigate to a meeting point in an unfamiliar town.

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Top questions

What languages is the tour guided in?

Live guide in English, Spanish and Italian.

Can children come?

Yes. Ticket types: Youth (12 to 17 years); Child (3 to 11 years). Children under 3 can't be included in the booking.

What is the Val d'Orcia and why is it on this tour?

The Val d'Orcia is a valley in southern Tuscany, designated a UNESCO World Heritage Site for its landscape of rolling hills, cypress-lined roads and isolated farmhouses. This tour travels through it to reach Montalcino and Pienza, and the route itself (the road stretching between the two towns) is considered one of Italy's most beautiful drives. Most of the day is spent in or crossing this landscape.

How much time do I actually spend in each town?

Montalcino and Pienza each get one hour of free time. That is enough to walk the main streets, take photographs, visit a shop or sit with a coffee, but not enough for a long meal or a museum visit.

Does the tour include lunch, and what kind of food is it?

Yes, a Tuscan lunch with wine is included. The operator does not detail the menu, but it is a traditional regional meal served as part of the day.

Do I need to arrange my own way to the starting point?

No. Hotel or apartment pickup in Siena is included, and you are dropped off at the same place at the end of the day.