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Tuscany Walking – Upgrade Level

Tuscany Walking – Upgrade Level

From 1270Euro per person

From Montepulciano to Siena

This tours comes from our best-seller “The walking in Tuscany tour” with a different selection of lodging and experiences, that makes the level of the tour upgrade. All the places that you are going to visit are the best level of accommodations and wine and food experiences so that you will bring a piece of Tuscany in your heart forever! 

Check what we have picked for you, in the “Tour Plan” tab below.

Walkthrough the very heart of Tuscany. We will stop in charming hilltop towns with spectacular panoramas, where you can climb feudal towers & see early Renaissance frescoes. Between the towns you will walk through the rolling vineyard hills, where you can stop to taste some of the best wines in the world. Your journey will end in the historic town of Siena, a UNESCO World Heritage Site & home to some of the most remarkable art & architecture from the 13-16th centuries. With its natural parks, centuries of culture, complex wine & perfectly simple cuisine, nothing beats the beauty of Tuscany.


  • Montepulciano & Pienza
  • Sant’Antimo Abbey
  • Walking through Val d’Orcia
  • Monte Oliveto Abbey
  • Stay in Siena


  • Wine tasting in a historical wine cellar in Montepulciano
  • Cheese farm visit in Pienza
  • Brunello wine tour and tasting in Montalcino
  • Cooing class in Bagno Vignoni
  • Taste Siena food tour ( )


We transfer your luggage

Just leave it at the reception desk with your name tag & you will find it at your next accommodation.

We book your hotels

We will book double rooms with private bathrooms in 2- or 3-star hotels, boutique B&Bs, or agritourism estates. You will find the vouchers to each hotel in your welcome package.

We supply detailed route notes & maps

The route notes can be in English, Italian, French, or German. All maps have GPS tracking.

  • Departure
    Montepulciano to Siena
  • Included
    7 NIGHTS ( in 3 Star Accommodation )
    All breakfast ( dinners on demand )
    Emergency number 24/7
    Gps Files Available
    Luggage Transfer
    Road Book & Maps
  • Not Included
    11 NIGHTS ( in 3 Star Accommodation )
    2 Dinners
    5 Dinner package ( On Request )
    5 NIGHTS in 3-4 Stars Accommodation
    6 NIGHTS in 3* / 4* Accommodation
    8 NIGHTS in 3* / 4* Accommodation
    Pilgrim's "Credenziale" ( Stamp book )
    Wine Tasting in Umbria

Day 1 – Chiusi –  Arrival and settling in

Arrival in Chiusi where you are met by our representative who will spend a short time going over the tour with you answering any question you may have. He will then drive you to your hotel in Montepulciano. UPGRADE LODGING: A charming suite in a BB in the city centre UPGRADE EXPERIENCES: A wine tasting in a spectacular wine cellar underground, in the city centre.

Day 2 – Montepulciano – Pienza

From the San Biagio church, the road leads you to Montichiello a nice little village immersed in the “Crete”. Stop there for a nice lunch or just for a cappuccino before continuing to Pienza, a jewel of Renaissance architecture. Walking time: 5 hrs UPGRADE LODGING: A beautiful relais with a stunning view of the city centre UPGRADE EXPERIENCES: A complete tasting of the world-famous Pecorino di Pienza, visit an organic cheese farm and enjoy the incredible landscape of Valdorcia 

Day 3 – Pienza – Bagno Vignoni

The Crete landscape is no doubt one of the most famous in the world: rolling hills in all the shades of brown or green; sturdy brick farmhouses crowning the hilltops and cypress-lined alleys design a perfect scenery that inspired painters since the Middle ages. Walking time: 4,5 hrs UPGRADE LODGING: Upgrade room in the Hotel Le Terme in the main square, enjoy your relaxing SPA after 2 days of walking UPGRADE EXPERIENCES: Cooking lesson and dinner with wine-pairing

Day 4 – Bagno Vignoni – Sant’Antimo

A quite hard day walking along dry river beds in a rather wild environment to reach St Antimo a lovely abbey isolated in the middle of a pastoral landscape w Enjoy the abbey and the evening chants of the monks while spending the night in a nearby agriturismo. In the evening you will reach Montalcino, the capital of Brunello wine; It is a nice medieval town with plenty of shopping possibilities well worth spending some leisurely time. Night in a hotel in Montalcino. Walking time: 5 hrs UPGRADE LODGING: Superior room with a view in Montalcino UPGRADE EXPERIENCES: Wine tour and tasting in a charming boutique Brunello winery

Day 5 – Montalcino – Buonconvento

Montalcino is the country of Brunello one of the most famous wine of this region so you will be walking through vineyards and olive trees. Walking time: 4 hrs UPGRADE LODGING: Superior room in your farm-house and Special Tuscan dinner UPGRADE EXPERIENCES: Wine tour and tasting in a charming boutique Brunello winery

Day 6 – Monte Oliveto – Siena

Start the day with a transfer to Monte Oliveto Maggiore, the construction of a red brick in a rugged landscape. Visit the abbey before the tourist rush hours and start walking back toward your hotel or agriturismo. Pick up your luggage and catch a train to Siena. Possible private transfer to Siena where we have booked a hotel for you. Walking time: 3h 30m UPGRADE LODGING: Deluxe room in a 4-star hotel in the city centre, few hundreds of meters to Piazza del Campo  

Day 7 – Siena

Siena is our last stop. Savour delicious icecream sitting at a Cafe on the hedge of the Piazza del Campo where the famous Palio is run twice in a year. Stroll the small “vicoli” and cobbled streets, admire the purity of the Duomo architecture and taste some of the best Italian wines at the Enoteca Nazionale before leaving to your next destination Walking time: 4 hrs UPGRADE EXPERIENCES: Join our "Taste Siena" food tour, a different way to visit this town, discovering its history, food and traditions.

Day 8 – End our service

See you next year to walk together!!

Accommodation Level

  Day 1 - Montepulciano   Day 2 - Pienza   Day 3 - Bagno Vignoni   Day 4 - Montalcino   Day 5 - Buonconvento   Day 6 - Buonconvento ( second night )   Day 7 - Siena
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