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Hike the hills of quintessential Tuscany, explore Montalcino, and discover lesser-known Tuscan villages.

This Tuscany hiking itinerary is filled with rural culture and authentic beauty. Val d’Orcia is the image of Tuscany itself: the landscape, with smooth hills, cypress trees that line its winding roads, lovely farmhouses and hilltop hamlets all correspond, in the mind of many people, to quintessential Tuscany. Even if you haven’t heard of Val d’Orcia before, you’ve certainly seen it. Pictures of the area dominate the covers and pages of many travel magazines that highlight Tuscany.

Val d’Orcia is a valley (Orcia is a river) south of Siena and it will set the stage for our peaceful exploration by foot via easy paths, forest roads, and quiet country roads. Remember that our pace will allow us to enjoy the landscape and the historical sites without any rush.

You start in the countryside on the outskirts of Pienza. You will visit medieval hilltop towns, abbeys, and lonely farmlands. From there, you will explore part of the Brunello production area and visit a winery. We should also mention that this area has been known since Roman times for its thermal springs. We will pay a visit to the quaint village of Bagno Vignoni, famous for its naturally hot water that spurts forth from the earth beneath Monte Amiata (a spent volcano). Olive trees, vineyards, and an abundant use of tuff are all characteristics of the landscape that you will notice during our walks.

Historically, the Etruscans dominated central Italy hundreds of years before the Romans, whom they heavily influenced. However, what we see today is mainly the imprinting of the Middle Ages that (luckily) has been left nearly untouched in modern times. In the Middle Ages, the St. Francis Way (Via Francigena), a pilgrimage route from Canterbury to Rome, crossed this territory and dotted the area with small villages, inns and abbeys where the pilgrims could rest and receive assistance. 

Not sure if you can do it? Contact us to schedule a call about how demanding the hikes are.


  • An iconic wine region: Montalcino-Brunello
  • UNESCO World Heritage Site (Val dOrcia)
  • Villages of Pienza, Montepulciano, San Quirico dOrcia, and Montalcino
  • Stunning hiking along rolling hills covered with vineyards and quaint medieval villages
  • The thermal spa village of Bagno Vignoni
  • Some of the best regional food in Italy
  • A visit with lunch at a Brunello di Montalcino producer
  • Learn about and walk part of the Via Francigena

Ask for custom dates for private groups.


Starting at USD 3,775

Private room (single supplement) USD 695


6 days (5 nights)



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Day by Day

[fa icon="plus"] Day 1

Pienza - 1 hr - Rolling

Your guide will meet you at the Florence airport for a late morning shuttle. You will settle in at your hotel in picturesque Pienza, arguably Val d’Orcia’s most significant town. Pienza is known for Pope Pio II, for pecorino cheese, and for its perfectly-preserved medieval center. Its hilltop location also affords a stunning view of the surrounding valley. We’ll have a lunch filled with the local specialties and check in at our quaint hotel.

Today’s hike covers Petroio and Sant’Anna in Camprena and the countryside in between. While these places might not ring a bell, they have been featured in some important movie blockbusters: The Gladiator had a dreamy scene among wheat fields over these hills, and Sant’Anna in Camprena set the stage for some of the scenes in the English Patient.

Free afternoon to relax and to explore the village. A tour overview with an aperitivo will lead to our first group dinner.

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Montepulciano - Montichiello - 3.5 hrs - Rolling

Our first full day of Tuscan exploration! UNESCO’s description of the Val d’Orcia is the following: “The landscape’s distinctive aesthetics, flat chalk plains out of which rise almost conical hills with fortified settlements on top, inspired many artists. Their images have come to exemplify the beauty of well-managed Renaissance agricultural landscapes.” Today’s hike will touch Montepulciano, medieval Monticchiello, and, finally, Pienza. All of these villages are easy to spot because of their dominant positions, and there will be plenty of photo opportunities! For lunch we’ll take a short detour to an agriturismo that will serve a simple, traditional lunch. Time to enjoy life with a glass of wine in your hand immersed in the idyllic Tuscan countryside! Back in Pienza, we visit the 15th century Papal Palace and cathedral.

[fa icon="plus"] Day 3

San Quirico d'Orcia - 3 hrs - Rolling

We follow paths across open country to the medieval village of San Quirico d’Orcia. Lunch is a picnic in the rose garden in town. San Quirico is not as well-known as Pienza or Montalcino but it’s more authentic and just as charming.

Back at your country stay, enjoy the pool and sunset with a glass of wine. A presentation of Via Francigena will put the last part of the tour into perspective and will frame some of the sites that we visit next.

[fa icon="plus"] Day 4

Bagno Vignoni - 2.5 hrs - Hilly

We walk through farmland and mostly along a ridge to Bagno Vignoni. At the halfway point we stop for a picnic lunch in the small hamlet of Vignoni Alto. Don’t forget to check out the church of San Biagio. The last part of the hike is mostly down among vineyards and sparse oak forests.

As you arrive in Bagno Vignoni, you’ll soon realize why this area has been known since Roman times for its thermal springs. The rest of the afternoon is all about relaxing in the thermal water pool which has a stunning view of the hill country surrounding the village (it’s also possible to book a massage). Dinner at the hotel restaurant.

[fa icon="plus"] Day 5

Montalcino - Sant'Antimo - 4 hrs - Hilly

Our last day starts and ends in Montalcino, the homeland of one of the kings of Italian and Tuscan wine: the Brunello, of course!

One of the best hiking routes in the area is the walk from Montalcino to the Sant’Antimo Abbey through shaded woodland and Brunello vineyards. Sant’Antimo Abbey is a beautiful Romanesque church built in the 12th century which was very important for pilgrims on the Francis Way to Rome. Built in travertine stone, the abbey stands in perfect isolation on a plain among secular olive groves and lovely wheat fields. For lunch we will organize a simple but hearty picnic at the abbey.

In the afternoon we visit a family-run Brunello  winery right in town. Final celebratory dinner at our favorite trattoria in the center of Montalcino.

[fa icon="plus"] Day 6

Transfer to Florence

Departure - Private transfer by Tourissimo from last hotel to the airport (Florence). Ask us about extending your stay in Montalcino or Siena.


What's Included

Upon request and free of charge, you can use our Ferrino Mustang light aluminum alloy walking poles (highly recommended). 

Ferrino walking poles

• One or two professional tour guides throughout the program
• All accommodations in one 3 and two 4-star hotels 
• All breakfasts, all lunches, and all dinners
• Wine and beer with meals, coffee, cappuccino, and gelato stops
• Wine tasting at a Brunello producer
Logistical support during the tour and luggage transfer
• Shuttle at the beginning and at the end of the tour
• All activities mentioned in the day-by-day description
• Airfare
• Pre-tour hotel stays and post-tour hotel stays
• Personal expenses such as laundry and cell phone
• Guide gratuity
• Optional tour extension




Hotel Posta Marcucci Bagno Vignoni


Hotel Dei Capitani Montalcino


More Info

Food and Wine

It's often pointed out that Tuscan cooking has its roots in "cucina povera" - peasant cooking. In truth, though, that can be said of most Italian cuisines. It's true, though, that Tuscan cooking is a simple one. There are no reductions, no fancy sauces, no elaborate creations, no heavy complicated seasoning.

Throughout Tuscany, olive groves and wild herbs are everywhere. Many of the best olive oils produced in Tuscany are reserved for use as a condiment at the table, rather than as an ingredient in cooking in the kitchen. Some of the best Italian reds are produced in Tuscany: Chianti, Brunello, Nobile di Montepulciano, not to mention the super-tuscans.

Val D’Orcia Natural and Cultural Park

The natural features of the valley, together with the cultural identity of the community that has lived there for centuries, make Val d’Orcia a unique area and for that reason it’s been designated a World Heritage site by UNESCO. The municipalities of Val d’Orcia are Castiglione d’Orcia, Montalcino, Pienza, Radicofani, and San Quirico d’Orcia.



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