Walking in Tuscany

€ 1150 (from) / Per person

Walking in Tuscany

From Montepulciano to Siena
Walk through 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.

  • 7 Days
  • Age 15+
  • Tuscany


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

Accommodation level

Day 1 – Montepulciano 

Day 2 – Pienza 

Day 3 – Bagno Vignoni 

Day 4 – Montalcino 

Day 5 – Buonconvento 

Day 6 – Buonconvento  

Day 7 – Siena 

How does it work

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 3- or 4-star hotels, boutique B&Bs, or agritourism estates. You will find the vouchers to each hotel in your welcome package.

We supply GPS files.

In order to be more eco-friendly, we will provide a GPX reader application with a user-friendly interface, allowing for easy and real-time navigation

Departure: Montepulciano
Destination: Siena
  • 7 nights (in 3/4 stars accommodation)
  • All breakfast (dinners on demand)
  • Emergency number 24/7
  • Gps files 
  • Luggage transfer
  • Dinners
  • Tips
  • Wine tasting

Tour Plan



Day 1: Arrival and settling in

Arrival in Montepulciano 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.


Walking time 5 h

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 4.5 h

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 Middleages. Your hotel has SPA facilities


Walking time 5 h

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 4 h

Day 5: Montalcino - Buonconvento

Montalcino is the country of Brunello one of the most famous wines of this region so you will be walking through vineyards and olive trees. Overnight in a beautiful agriturismo near Buonconvento.


Walking time 3.30 h

Day 6: Monte Oliveto Loop

Start the day with a transfer to Monte Oliveto Maggiore, a red bricks construction in a rugged landscape. Visit the abbey before the tourist rush hours and start walking back toward your agriturismo.


Walking time 4 h

Day 7: Siena

Siena is our last stop. Savour a delicious ice-cream 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


Day 8: End our service

See you next year to walk together!!

Photo Gallery