Tuscany: hilltop towns of Val d’Orcia & Siena

€960 per person

Travel through the most iconic cultural landscape in Italy and experience a beautiful explosion of natural and cultural heritage throughout this amazing self-guided walking tour. The Tuscan landscape of the Val d’Orcia will charm you with its vineyards, scenic farmhouses, green forests, and peculiar iconic eroded clay slopes. As you advance through the wonders of the Tuscan countryside, you will discover captivating settlements such as the hot spring hamlet of Bagno Vignoni and the Renaissance city of Pienza. A true cocktail of experiences, this independent hiking itinerary brings you to beautiful palaces, thermal baths, Romanesque churches, and tempting local wineries while walking through beautiful valleys, playful rivers and enchanting forests. Enjoy an exciting trip deep into the pearl of central Italy hopping from one hilltop village to the next.

  • Destination
  • Duration
    8 Days I Level: 2 (of 5)
  • What is included
    Accommodation in 3* hotels and agriturismo incl. breakfast; Luggage transportation; People transfer (on Day 4 (to Castelnuovo), on Day 6 (Buonconvento-Monte Oliveto Maggiore Abbey) and on Day 7 (Buonconvento-Monteroni d'Arbia); Detailed roadbook and map in English (incl. access to GPS tracks); Emergency hotline
  • What is not included
    Drinks and other meals; Other transfers/Public transportation; Possible CITY TAX to be paid in cash on the spot (it varies depending on the city and on the hotel’s category; appr. 1-3 Euro per person per night)
  • Best period
    April, May, June, July, August, September, October
Day 1. Arrival at Montepulciano
Your great green Tuscan adventure begins in the charming hill town of Montepulciano. It is convenient to reach from either Rome, Florence or Pisa by train to Chiusi. From there, catch the local bus or enjoy a comfortable taxi ride to beautiful Montepulciano. Leave some time to explore this delightful Renaissance gem.
*Always let us know in advance if you plan to arrive by your own car in Montepulciano!
Day 2. Montepulciano - Pienza (13-15km, 4hrs, +390m/-500m)
Your first walking day starts from the San Biagio church in Montepulciano where you quickly find yourself on the trail to the quiet village of Montichiello. Take a break and enjoy a local meal or just pause for a cup of nice cappuccino before you get back on the trail to the extraordinary Renaissance town of Pienza. A UNESCO World Heritage site since 1996, the charming old center of Pienza is also a great place to try some delicious local pecorino cheese and truffles.
Day 3. Pienza - Bagno Vignoni (12km, 4hrs, +200m/-420m)
After a healthy breakfast, the self-guided hiking route will take you on a walk through fragrant forests, green hills, and delightful villages. Your destination is the wonderful thermal complex of Bagno Vignoni where you can spend the afternoon pampering yourself.
Day 4. Bagno Vignoni - Sant’Antimo - Montalcino (13km, 4,30hrs, +450m/-280m)
After a relaxing afternoon at the SPA the previous day, you will engage in some healthy exercise. A morning transfer will take you to the medieval village of Castelnuovo dell’Abate, where you will have time to enjoy the enchanting isolated abbey of Sant’Antimo (former Benedictine monastery), offering a wonderful panorama of the pastoral landscapes around. The walking trail towards Montalcino is extremely panoramic, with fabulous views over the Orcia Valley while the last few kilometers you will walk in the shade of the woods. Montalcino is one of the most famous hilltop towns in Tuscany, known worldwide for its exquisite wines.
Day 5. Montalcino - Buonconvento (15-18km, 5hrs, +320m/-620m)
An exciting day of independent walking in the outstanding Brunello wine region awaits you. You will walk pass orderly vineyards and olive groves as a wonderful Tuscan landscape of the Crete Sensi and Buonconvento reveals itself.
Day 6. Loop walk to Monte Oliveto Maggiore Monastery (14km, 4,30hrs, +390m/-460m)
Today’s self-guided hike begins with a transfer to the monastery at Monte Oliveto Maggiore. Take the time to explore the impressive red brick abbey and the amazing Tuscan landscape in its surrounding. You will then walk back to Buonconvento in this fairytale landscape.
Day 7. Monteroni d’Arbia - Arbia; train to Siena (10km, 3,30hrs, +230m/-190m)
The last day of your independent walking tour is dedicated to the wonderful city of Siena and the beautiful surrounding area. You will start the day with a short transfer to Monteroni d’Arbia after breakfast where the trail you will follow begins. Hike through the iconic landscape of rolling hills and harming hamlets until the breathtaking sight of the unique city of Siena reveals itself before your eyes. Once you reach the train station of Arbia hop on the train to Siena and take the time to explore the city for the rest of the day. Make sure you visit the impressive Duomo and the beautiful medieval palaces. Take some pictures for your travel book at the most famous shell-shaped square in Europe - the Piazza del Campo.
*Optional private transfer from Arbia train station to Siena (140 Euros for a group of up to 4 pax; should be requested at the time of booking)
** Some customers prefer to skip this last walk in order to have e full day to explore Siena. Should you wish to do that, please advise your plans already at the time of booking.
Day 8. Departure day
The tour and our services end after breakfast. We highly recommend you book some extra nights in Siena to experience the beautiful city in full. If you choose to continue your travels today, head to Florence by local bus.


960 Euro per person in twin/dbl room
* Triple rooms for odd number of travelers available upon request (contact us for details)
Single room & Solo Traveler supplement
Single room supplement: 290 Euro
Solo traveler supplement: 560 Euro (incl. sgl. room supplement)
Daily departures between the beginning of April and the of October. The route is quite easy, with ups and downs typical of the Tuscany’s rolling hills. The whole itinerary is mostly on paths and gravel roads ("strade bianche"), even if you will find some sections on asphalted road. Florence, Pisa and Rome airports are flown to by both major and low cost international carriers. All three airports can be easily reached by local transport, which is affordable and offers a frequent service.
By Train from the airports to Montepulciano: From Rome: From the two major Rome airports take the bus or train to Rome Termini train station. From Roma Termini train station take the direct train to Chiusi-Chianciano Terme (train ride takes approx. 1,40hrs, ticket costs appr. 10-12 Euros). From Chiusi-Chianciano Terme take the bus to Montepulciano (line FT4 bus ride takes 25 min.) From Florence: Florence train station take the direct train to Chiusi-Chianciano Terme (train ride takes approx. 2,15hrs, ticket costs 14-15 Euros). From Chiusi-Chianciano Terme take the bus to Montepulciano (line FT4 bus ride takes 25 min.) Departure: By Train from Siena to the airports: Check the updated timetables on the website To Pisa Airport: From Siena take the train to Pisa Centrale. Train journey to Pisa takes approx. 1 hour and 45 min., ticket costs 12-13 Euros. From Pisa Centrale you can take a bus, train or taxi to reach Pisa Airport.  To Florence Airport: From Siena take the train to Florence Santa Maria Novella. Train journey to Florence takes approx. 1,30hrs, ticket costs 10-12 Euros. From Florence Santa Maria Novella you can take a bus or taxi to reach Florence Airport.
IMPORTANT: Always let us know if you arrive by car or by public transport because if you come by car we have to change the standard hotel in Montepulciano and go for another hotel that has a parking lot (the latter goes with a small supplement). If you book the optional transfer from Arbia to Siena, you must call or send a message to the carrier about 2 hours before the arrival in Arbia so he can be there to pick you up. Always comply with the pick up times for the transfers as specified in your roadbook.
We use selected 3* and 4* hotels and agriturismo (1x night in Montepulciano; 1x night in Pienza; 1x night in Bagno Vignoni; 1x night in Montalcino; 2x nights in Buonconvento; 1x night in Siena). Some of the accommodations chosen have a swimming pool and internal restaurant. All rooms in the accommodations have en-suite facilities. Throughout the trip, there are plenty of opportunities to taste both the great local food and a wide array of prestigious wines of the region. Breakfasts are included everywhere.
N.B.: In Fattoria Pieve a Salti in Buonconvento you can either stay in the reception area, where the outdoors swimming pool and restaurant are situated (but only few rooms there!) or in the beauty farm area (only 1 km away) where the horse stable and the indoors swimming pool are; we will always mention if you stay in the beauty farm area (if this is the case the inn will arrange a free shuttle to and from the restaurant for dinner).

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