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Walking in Tuscany

Walking in Tuscany

From 870Euro per person

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.


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


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.

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 – Monte Oliveto – Siena

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 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


Day 7 – Siena

Siena is our last stop. Savour a 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


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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