Language
English,
Transportation (C)
Train, Bus, walking
Departure from
Montepulciano
Arrival to
Siena
Level of difficultly
2
Comfort Level
3
Accomodation
selected 3* and 4* hotels and agriturismo
Meals
some meals included
Guiding method
Self-guided
Minimum Age
18
Destinations
Siena, Tuscany
Activities
Walking Packages
Trip Tag
Self guided Tour

Highlights

Itinerary

Map

Dates & Costing

Inclusions

Accommodation and Meals

Additional Information

Payment and Cancellation

Experience the heart of Val d’Orcia on this walking journey through Tuscany’s iconic landscapes. Hike through steep valleys, dense forests, clay “badlands,” and past olive groves, fig trees, and vineyards.
Relax in the thermal waters of Bagno Vignoni, explore the Renaissance charm of Pienza, and wander hilltop towns, Romanesque churches, and prestigious wineries. End your days with a toast of Brunello di Montalcino amid unforgettable scenery.

Level of difficulty 2 = Moderate day walks of 3-5 hours per day (excluding breaks) in hilly to mountainous areas using well-maintained, sometimes stony paths.

Comfort level 3 = Good hotels, inns, B&Bs, agriturismo (farmhouses) with en-suite private bathrooms, often well-located and serving good meals.

Highlights

Natural, artistic and cultural treasures of Val d’Orcia, a UNESCO World Heritage Site
Wide-open fields, cypress-lined hills, famous vineyards
Exquisitely preserved Medieval and Renaissance villages
Peaceful country roads, friendly Tuscan locals and delicious regional specialties
Warm friendly locals
Stress-free luggage and routing

Day 1 :

Monetepulciano

Make your way to Montepulciano. Your walking tour of Tuscany begins in the medieval and Renaissance hill town.
Spend the next week soaking up the striking scenery of the rolling Tuscan countryside.

Day 2 :

Walk from Montepulciano to Pienza (13 - 15 km)

Starting from the Church of San Biagio, you will travel down a quiet country lane and suddenly lose yourself in the tranquil beauty.
You will soon reach the tranquil village of Montichiello, where you can enjoy a relaxing lunch or a quick cappuccino on the way to Pienza.
Picturesque Pienza is a UNESCO World Heritage Site with unique Renaissance architecture and is home to delicious Pecorino cheese and truffles.
It is the perfect place to enjoy Tuscan cuisine.

Challenge: 4 hours, 13 – 15 km, 385 m ascent, 505 m descent

Breakfast

Day 3 :

Walk from Pienza to Bagno Vignoni (12 km)

Today, hike through an incredibly perfect landscape of rolling hills, majestic oaks, cypresses, and photogenic villages.
Relax in the thermal springs of Bagno Vignoni and trade the warm Tuscan sun for steamy, soothing waters.

Challenge: 4 hours, 12 km, 195 m ascent, 420 m descent

Breakfast

Day 4 :

Transfer to Castelnuovo dell'Abate, walk to Montalcino (13 km)

Today, you will walk mainly on wide dirt paths.
Once you reach the village of Castelnuovo dell’Abate, take time to enjoy the breathtaking beauty of the Abbey of Sant’Antimo, a former Benedictine monastery dating back to the 8th century.
The first part of the route to Montalcino is very panoramic, offering stunning views of the Val d’Orcia. The last kilometres take you through the forest.
Once you arrive in Montalcino, relax and enjoy a glass of excellent local wine.

Challenge: 4 hours, 13 km, 450 m ascent, 280 m descent

Breakfast

Day 5 :

Walk from Montalcino to Buonconvento (15 -18 km)

A hearty breakfast will prepare you for a long and beautiful day of hiking in the famous Brunello wine region. You will pass through vineyards and olive groves and enter the beautiful Tuscan countryside of Crete Sensi and Buonconvento.

Challenge: 5 hours, 15 -18 km, 316 m ascent, 619 m descent

Breakfast

Day 6 :

Loop walk to Monte Oliveto Maggiore Monastery (14 km)

Your short, undulating day begins with a transfer to the Abbey of Monte Oliveto Maggiore, a striking red-brick monastery set in the rugged Tuscan countryside.
After an early visit to avoid the crowds, you’ll return to Buonconvento on foot.

Challenge: 5 hours, 14 km, 382 m ascent, 460m descent

Breakfast

Day 7 :

Transfer to Monteroni d’Arbia, walk to Arbia & train to Siena (10 km)

A short transfer will take you to Monteroni d’Arbia, from where you will continue on foot to Siena.
You will pass through hills and villages until the unmistakable silhouette of the city appears in the distance.
In Arbia, you will board the train to Siena and spend the night amid the splendid beauty of the city: the great Piazza del Campo, the joyous Cathedral, and the medieval palaces that recall the “trade” of a city that took part in the dangerous wars, in which the “Palio di Siena” also took part.

Challenge: 4 hours, 10 km, 225 m ascent, 185 m descent

Breakfast

Day 8 :

Final day

The trip ends after breakfast unless you have booked a transfer to the station or airport or other services like accommodation elsewhere in Italy or the rest of the world…

Breakfast

Accommodation and varies

Accommodations are carefully selected because of their location, atmosphere and/or unique services.
We choose comfortable hotels, farmhouses and B&Bs where all rooms have private en-suite bathrooms.
You can find below the standard hotels for this trip. If a hotel is fully booked, then we will book a similar one for you and inform you about the alternative booked.
Extra overnight: You can book additional night(s) at any of the accommodations along the way.

Hotel Il Duomo (Montepulciano): in the old town center near the Piazza Grande, is a small, welcoming, family-run hotel situated in an old Renaissance Palazzo. What sets the Duomo apart is the attention we pay to our guests, creating a relaxing and intimate atmosphere for the duration of your stay.

Piccolo Hotel La Valle (Pienza): Walking along the city walls of the town of Pienza in the direction of the Val d’Orcia, there is a building made of stone and brick, Il Piccolo Hotel La Valle. Its strategic position, a stone’s throw from the historic centre and its panoramic garden patio make it an ideal place to have magic and to relax and stay immersed in culture, unspoiled nature, gastronomy & handcrafters. There are numerous activities and experiences that can be enjoyed while spending a vacation in one of the most fascinating areas of Tuscany.

B&B La Locanda del Loggiato (Bagno Vignoni): This isn’t an ordinary bed & breakfast in Val d’Orcia, it isn’t just a ‘place to sleep’, it’s a refuge where charm and romanticism blend with simplicity. The Locanda del Loggiato dates back to 1300, it will take you back in time and allow you to discover the delights of one of the most magical spa villages in Tuscany, Bagno Vignoni.

Albergo Il Giglio (Montalcino): Il Giglio opened at the end of the 19th century as a coach house where travellers could find a place to eat and sleep, and horses could rest after the steep climb to Montalcino.

Agriturismo Pieve a Salti (Buonconvento): The Borgo of Pieve a Salti is nestled in the rolling hills of Siena in a beautiful natural setting rich in history, art, and sacred traditions. Its houses, inside the old village overlooking the surrounding hills, offer hospitality in comfortable rooms with bathrooms or typical apartments of various sizes.

Hotel Chiusarelli (Siena): Hotel Chiusarelli is located right in the historic centre of Siena, a city of art that still nowadays remains rooted in its traditions, among which is the famous Palio. The hotel is set in a neoclassical villa built in 1870. The renovation has added a modern touch keeping however, the original style of the palace, with its magnificent frescoed rooms, makes our guests feel like they are stepping back in time.

Extras on request:

Additional nights before, during or after the walk
Single Room Supplement(s)
Solo Traveller Supplement
Transfer from Arbia train station and transfer to Siena (If clients have booked this optional transfer, they MUST call or send a message to the carrier at least 1 hour before the arrival in Arbia so he can be there to pick them up)
Transfer from Amalfi to Napoli or Salerno airport/station

Technical Information

The walks are along vineyards, uneven footpaths, mule tracks and small gravel roads (strade bianche). The trails through the vineyards can get slippery, muddy and heavy-going when wet or after it has rained. The trails do not always have markings.

Luggage transfer is included in your package; this is normally provided by the accommodation itself or by a local taxi. The allowance is : only 1 piece of luggage of 20kg per person (if they have it really big, they must mention it at the time of booking, additional cost may be required)

A note on the self-guided adventures and Fitness preparation:
Self-guided walking requires individuals to use problem-solving skills, be adaptable and have a keen eye. You should be comfortable reading maps, referring to route notes, and having a good sense of direction (or be willing to work on improving this!) Sometimes route finding, losing your way, finding it again and asking the locals for help is part of the adventure. If you’ve never been on a self-guided trip, you will get the hang of it after the first couple of days, as most of our first-time travellers attest. Please be assured that our written material issued to you for route finding is updated regularly, and we provide a 7-day service hotline in case of any problems. A certain level of the unknown comes with self-guided trips; however, with a systematic approach, potential problems will be averted. The freedom of a self-guided journey is something that, once experienced, is sought repeatedly.
Fitness preparation: The concept behind most of our trips is active holidays; the fitter you are, the more quickly you will adjust and enjoy yourself. We expect participants to take responsibility for their fitness and preparations consistently before departure and INCREASE the regular weekly training schedule in the two months following release. That way, when you start walking, you will feel relaxed, comfortable, and strong, having done more than sufficient preparation for the trip. You will also have more energy to enjoy the views, take photos and explore the sights in your spare time rather than make it to the next hotel. While the day is when the most exciting features of interest will be found, and being fit allows you to optimise every situation you encounter. At a minimum, we recommend 40 minutes of aerobic exercise: running, swimming, biking, hill walking, or gym work two to three times a week for two to six months leading up to your walk. Note that the best training is the activity you will be doing: walking up and downhill and cross-country. Practice this as much as possible. Training should be stepped up as you get closer to departure to an appropriate amount (you don’t want to cause yourself an injury!). Using your gear before departure (boots, day pack, clothing, etc.) gives familiarity and comfort whilst walking. It makes sense to know that all your gear ‘works for you’ BEFORE departure, rather than discovering how things work or fit (or don’t!) on the trip you have invested so much in. Use the philosophy of ‘getting fit to go walking’ rather than ‘going on a walk to get fit’ to avoid problems.