Hill Towns of Tuscany Map and Itinerary

DAY 1: Arrive Starting Point: Montepulciano

We recommend flying to Rome, Florence or Pisa and then catch the train to Chiusi (Train 1h30, 2h30 and 1h50 respectively).From Chuisi you can take a local bus or taxi the short distance to Montepulciano (20mins)

Overnight: B&B l'Agnolo
Located in the heart of Montepulciano. This once grand home is now a beautiful small and comfortable Bed and Breakfast, still displaying the ornate high fresco ceilings and wonderful surroundings. Expect a warm welcome during your stay in this unique bed and breakfast. 

DAY 2: Montepulciano to Pienza: 9.5 miles

Starting from the San Biagio church you follow a quiet dirt road to the charming village of Montichiello where you can pause for a relaxed lunch or perhaps just a quick cappuccino before continuing to Pienza. Pienza is a UNESCO World Heritage site because of it’s unique renaissance architecture and town planning. Additionally it is well known for the production of pecorino cheese and truffles.

Overnight: Hotel Pienza San Gregorio
Hotel Residence Pienza San Gregorio offers a tranquil retreat just meters away from the ancient walled town. Large comfortable rooms, a lovely restaurant serving traditional Tuscan food and an outdoor swimming pool combine to make this a favourite stop. 

DAY 3: Pienza to Bagno Vignoni: 9.5 miles

Today you wander through a beautiful region of rolling hills, oak woods, cypress trees and pretty villages. The thermal baths complex at Bagno Vignoni is the perfect location to spend the afternoon relaxing.

Overnight: Albergo Le Terme
Depending on availability you will stay at Albergo Le Terme, which is in the centre of town and is surrounded by steam from the thermal springs or a lovely agriturismo 2 km outside town on the trail.

DAY 4: Bagno Vignoni to Sant’Antimo: 8 miles

A hard but enjoyable day following dry riverbeds through a fairly wild environment brings you to St Antimo, an isolated abbey situated in a pastoral landscape. After exploring the abbey we will transfer you to the Medieval town of Montalacino.

Overnight: Hotel Dei Capitano - Montalcino
Hotel Dei Capitani is fantastically positioned in the centre of the Medieval town, offering wonderful panormaic views over the Tuscan landscape, from the beautifully designed swimming pool and terrac. You will experience warm Tuscan hospitality, in this charming Hotel.;

DAY 5: Montalcino to Buonconvento: 14 miles

A fairly tough day walking in the famous Brunello wine region. You will pass tthrough vineyards and olive groves, then finally entering the beautiful Tuscan Landscape of the "Crete" and Buonconvento, where you will stay in a lovely agriturismo.

Overnight: Fattoria Pieve a salti -Buonconvento
For the next two nights you will stay at a traditional Tuscan agriturismo (country hotel), with a fabulous outdoor swimming pool, spa and various other activities on offer. The restaurant is ecxcellent,  rustic in style and serving delicious food home grown on the estate.

DAY 6: Buonconvento to Monte Oliveto Maggiore/Siena: 7.5 miles

A short day which is full of ups and downs. You start with a transfer to the Monastery at Monte Oliveto Maggiore, an impressive abbey built of red brick and set in the rugged Tuscan landscape and after an early visit which avoids the crowds you walk back to Buonconvento, perhaps stopping for a freshly made panini.

Overnight: Fattoria Pieve a salti - Buonconvento

 DAY 7: Buonconvento to Siena: 10 miles

Today you will start with a short transfer from Pieve a Salti to Grancia di Cuna to start the walk to Siena. Walking through a landscape of rolling hills and small hamlets until you are rewarded with the view of Siena in the distance. Enter the town through Porto Romana, one of the medieval gates and walk thought the city to reach your hotel. Overnight: Siena. .

Overnight: Hotel Chiusarelli, Siena.
After exploring Siena you will find the comfortable three star Hotel Chiusrelli with it’s views over the old city the perfect base. 

DAY 8: Onward Travel From Siena

You can catch the train to the airport or perhaps your next destination in Italy.

Recommendations

Additional Nights

Many of our clients choose to add extra nights along the walk to sample more of the wonderful walking and attractions available in Tuscany. If you choose to extend your holiday we would recommend spending extra nights in Pienza, Montalcino or Siena.

Fewer Nights

If you wish to reduce the number of nights we can tailor your trip to your requirements.

Extensions

Why not extend your time in Italy with a few nights in Florence, Rome or even Venice? We offer several short city extensions and would be happy to tailor one to your needs.

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