Hilltop Towns of Tuscany

Self-guided Tour - 8 Days / 7 Nights

The quintessential Tuscan scenery between Montepulciano and Siena is what dreams are made of. Stay in medieval walled towns and taste the famous vintages of the area – Chianti and the rich red, world renowned Brunello wines.
Follow pleasant trails in the countryside that is a patchwork of vineyards, olive groves, ancient forests and fields of wheat and barley – the wellspring of ingredients for delicious Tuscan meals!

Your Journey

Day 1

Arrive the medieval walled town of Montepulciano with panoramic views over the surrounding countryside. Arrival transfer from Chuisi train station included.

Day 2 Montepulciano – Pienza (15 km)

Walk to UNESCO World Heritage Pienza, a Renaissance jewel.

Day 3 Pienza to Bagno Vignoni (14kms)

Walk classic Tuscan countryside to Bagno Vignoni, famous for its Roman and Renaissance thermal baths.

Day 4 Bagno Vignoni – Sant. Antimo (15 kms)

Discover the charming Benedictine Monastery of Sant Antimo, an example of Romanesque architecture in Tuscany. You may hear the Gregorian chants of the monks who live there. Transfer to the hilltop town of Montalcino, famous for the Brunello wine and dominated by its imposing ‘rocca’ (fort).

Day 5 Montalcino to Buonconvento (18kms)

Walk through Brunello vineyards to enter the ‘Crete’ landscape of Siena. Stay in a lovely agriturismo.

Day 6 Buonconvento to Monte Oliveto Maggiore (13 kms)

Transfer to the monastery at Monte Oliveto Maggiore, an impressive abbey built of red brick then walk back to Buonconvento. Afternoon transfer to Siena.

Day 7 Siena

Enjoy a walking tour of one of Europe’s best preserved medieval cities including the main square, Il Campo, scene of the annual Palio horserace.

Day 8

Arrangements end.


Moderate walking on farm tracks and quiet roads with some hilly terrain.


Breakfast daily.

Price 2020

Please note pricing is in Euros.

2020 (Twin Share):  €1110

Single Supplement from €145.


Start any day 01 April - 24 October.


The above is a short synopsis of this tour. This email address is being protected from spambots. You need JavaScript enabled to view it. for a more detailed itinerary and trip notes.

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A Walker’s World has been offering walking holidays in Europe and around the world since 1991.

  • Our experienced team can advise and coordinate your travel arrangements to your personal requirements.