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Hill towns of Tuscany – Highlights

Hill towns of Tuscany – Highlights

From 650Euro per person

From Montepulciano to Buonconvento
Walk through the most famous hills of Tuscany: Val d’Orcia. A UNESCO World Heritage landscape, these rolling vineyards with cypress-lined roads & patchwork fields inspired the notable Renaissance artists of the Sienese School during the 13-15th centuries. As you traverse these very hills, you will stop in the Renaissance jewel of Pienza, another UNESCO World Heritage Site renowned for its Renaissance masterpieces & charming cobblestone streets. Explore many other small medieval towns, often still encircled in defensive walls, where you can stroll the artisan boutiques, climb feudal towers & enjoy the spectacular wine & cuisine of the region.
Your trip will end in the charming hilltop town of Montalcino, known for the eponymous wine. Here you can celebrate the end of your long journey with a wine tasting paired with artisan pecorino cheeses.


> Visit Montepulciano and Pienza
> Sant’Antimo Abbey
> Walking in the Valdorcia
> Bagni Vignoni


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.

  • Destination
  • Departure
    Montepulciano to Buonconvento
  • Included
    5 NIGHTS in 3-4 Stars 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 )
    6 NIGHTS in 3* / 4* Accommodation
    7 NIGHTS ( in 3 Star 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.

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 Renaissence architecture.

Walking time: 5 hrs


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 scenary that inspired painters since the Middleages. Your hotel has SPA facilities

Walking time: 4,5 hrs


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


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


Day 6 – 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


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