Southern Tuscany – Lovely Landscapes

Hiking program with guide – 6 days, 7 nights

This hiking vacation takes place in one of the most picturesque areas of Italy: the Orcia Valley which recently has been declared a UNESCO World Heritage Site. You will discover a part of Tuscany which enchants its visitors with unique landscapes, rolling hills with olive groves, cypress avenues, vineyards, ancient abbeys and medieval towns. We recommend visiting this area in springtime when the gorse blooms or in autumn during the grape harvest. Your professional hiking guide will take you on various hiking trails to explore this gorgeous territory. Be prepared to see magical places full of history and to taste delicious picnics and great wines including “the great Tuscans”: Chianti, Brunello di Montalcino and Nobile di Montepulciano. The hotel accommodation is organized in a beautiful country house with delicious Tuscan cuisine in a fantastic location.

Benvenuti in Toscana!

1st day: Arrival at the country house. In the early evening, all participants meet in order to get to know the hiking guide and discuss the travel program of the next few days. A delicious aperitif with local snacks is the perfect way to start this hiking week in Southern Tuscany.

2nd day: The first hike of this trip will lead you through the picturesque Orcia Valley, a UNESCO World Heritage Site. You will explore the historic towns of San Quirico and Bagno Vignoni, the latest being an ancient thermal town where the legendary Medici family and Saint Caterina of Siena sought healing. After the hike, it is very refreshing to dunk your tired feet into the healing water. In Bagno Vignoni, we rest some more for lunch break and several restaurants invite you to taste the delicious Pecorino cheese. Then, we drive to a winery not far away. After a hearty welcome you will be able to enjoy their delicious wines which are produced according to biodynamic principles – very, very tasty!
Hiking route: approx.6.5 km, + 150 / -210 m, approx. 2 hours

The Crete Senesi hillside

3rd day: Today, we will hike through the dramatic landscape of the Crete Senesi hillside – an interesting limestone formation that gives the area a dreamlike appearance. Between the medieval villages of Chiusure and Buonconvento the gorse bushes bloom abundantly in spring. We start the day at the Benedictine Abbey of Monte Oliveto Maggiore, which is famous for its beautiful cloister with an impressive fresco cycle from the 15th century. Do not miss a visit to the monastery shop where the monks sell their handmade cosmetics and herb products. At lunchtime, you will stop in Chiusure for a hearty picnic with cheese and local vegetables. In the afternoon the path leads back to the country house.
Hiking route: approx. 18 km, + 250 / – 400 m, 5 hours of pure walking time

Picturesque Tuscany & Vino Nobile Wines

4th day: This morning we have planned a stroll through Pienza, also called the “ideal city”. The town is named after its most famous citizen: Pope Pius II. After he was appointed Pope, he decided to transform his hometown into the ideal city. After this interesting visit, we start hiking along another charming trail and crossing some of Tuscany’s most picturesque areas. In the idyllic village of Monticchiello we will have lunch in a typical Osteria and taste their homemade Pici (Tuscan pasta). In the afternoon, we will visit one of the best producers of the Vino Nobile di Montepulciano wine.
Hiking route: approx. 6.5 km, + 190 / -210 m, 2 hours of pure walking time

Dolce far niente!

5th day: A day at leisure. You might want to plan an individual trip to Siena or you can go horseback riding in the picturesque landscape around the country house.

6th day: You can’t be in Tuscany without drinking a good glass of Chianti wine. Therefore, our hike today brings us into a completely different landscape: the territory around Siena and Castelnuovo Berardenga has more woodland and the soil conditions are different too. After our daily workout during the hike, we then tour a winery with an important history. The land it stands on once was cultivated by the Etruscans – Tuscany’s first inhabitants – and later an abbey was built there. Today, we find an organic wine farm that produces not only wonderful wines but also fine olive oil and cereals.
Walking distance: approx. 15 km, +/- 250 m, 4 hours of pure walking time.

Harmonious Vineyards

7th day: The day begins in Montalcino, hometown of the famous Brunello wine. After a tour in the village, we start our hike which leads through magnificent vineyards and Mediterranean macchia. We will enjoy breathtaking views over the scenic surroundings. At noon we reach a winery which is managed by an enthusiastic winegrower and his charming wife. The location is marvelous, overlooking the medieval abbey Sant’Antimo in the distance. After a tour through their vineyards and the wine cellar, our hosts will delight us with a tasty lunch and their wines. Before heading back to the country house, you can visit the ancient abbey. A fascinating place, sober, simple, but full of magic, in a picturesque location, framed by ancient olive trees and cypresses.
Hiking route: approx. 7.5 km, + 40 / – 300 m, 2 hours of pure walking time.

Arrivederci e alla prossima!

8th day: departure or extension of your stay.


  • From € 1.279,00 per person in double room

    This price refers to a minimum of 10 participants. Please write us for a tailor made quote and experience!

  • € 275,00 surcharge for the single room


  • 7 nights with breakfast in a double room with bathroom in the Country House Pieve Sprenna with 6 x dinner.
  • Accommodation in rooms or apartments.
  • Hiking guide for all hikes, bus transfers in private buses according to the program.
  • Wine tasting with visits to the Poliziano, San Polino, Pacina wineries. 2 x lunch or picnic, 1 x vintner’s snack at La Magia.


Via Discovolo 252/a
19017 Manarola (SP)


+39 0187 760083

+39 0187 760798


Via Veneto 11
19124 La Spezia


+39 0187 19 87 730

+39 0187 19 87 732


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