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Walking Tour in Tuscany - Montalcino to Montepulciano
(6 days / 5 nights - $1,990 AUD per person or $1,690 AUD with 'No Dinners' Option)
Wine and Cooking Option
(3 days / 2 nights - $1,200 AUD per person)
Sant'Antimo, Tuscany

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This walking tour in Tuscany can be personalised to meet your interests and travel dates. This walk is family friendly walk: while not ‘easy' this Grade 1 walk follows well-marked paths and is suitable for fit children 10 years and above.
Starting with a private transfer from either Siena or Chiusi railway station (on the Rome/Florence line) to the charming medieval town of Montalcino, this walking tour in Tuscany crosses the Orcia River Valley in southern Tuscany, passing through some of the most beautiful country in central Italy, before arriving in Montepulciano, ‘pearl of the Renaissance'. It is an area as famous for its rolling hills, wheat fields dotted with red brick farmhouses, stands of deep green cypress pines and endless views as it is famous for its wines and food.
The medieval road that bisects the valleys was for several centuries the principal way linking Papal Rome with northern Europe, carrying pilgrims, traders, Crusader armies, emperors and popes. It was the scene of bitter fighting between Siena and their great rivals in Florence for several centuries and is lined with castles, monasteries and villages that date from this period. Most of the paths and thoroughfares that you follow also date from the era.
The walk also takes you to some of the cultural treasures of southern Tuscany: a beautifully restored pilgrim town with a large pedestrian centre; a magnificent papal town and the Renaissance architecture of Montepulciano.
"I'm back from my holiday and back at work! My walk from Montalcino to Montepulciano was marvellous and, given the opportunity, I'd do it again tomorrow! I've certainly told friends what a great time I had and would recommend it to anyone."
BN, 2008

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What's included in this walk? |
- Five nights accommodation
- all breakfasts and dinners
- lunch recommendations
- reading lists and historical and cultural notes
- maps and detailed walking instructions
- daily transfers of baggage between hotels
- pick up at either Siena or Chiusi (on the Rome/Florence rail line) and drop-off at the end back in Chiusi
- 24 hour backup from local manager
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How hard are the walks? |
Grade 1 Walk - Good paths, straightforward orientation, most walks 10 to 12 kms, no long climbs.
The country is beautiful and varied, the longest walk is 12 kms, although there are some hills they aren't too challenging. The paths generally follow gravel roads and all the walks are clearly marked.
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What's the accommodation like? |
Accommodation is in comfortable, family-run hotels. Costings are calculated on two people sharing a double room. All rooms have en suite bathrooms.


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Tour Cost: |
AUD $1,990 per person (single supplement for a double room for single use $350)
(approx US $1,780, SS $230 - subject to daily exchange rates)
Tuscany 1 'No Dinners' Option
AUD $1,690 per person
(approx US $1,500 - subject to daily exchange rates)
Montalcino Wine and Cookng Option
AUD $1,200 per person
(approx US $980 - subject to daily exchange rates) |

 Tour Snapshots: (click the image for a larger version)


Montalcino, Tuscany

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Flower Markets, Montalcino

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Tuscany Road

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Romanesque carving

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Fortress, Montalcino

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Festival, Montalcino

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Street scene

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Convent, Day 3

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You will be picked up at either Siena or Chiusi and taken to Montalcino, a perfectly preserved walled hilltop town, famous for both its views and its red wine, Brunello di Montalcino. Included in your notes is a short walk around the outside of the town's walls. |
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The first walk takes you down through forests to a Romanesque abbey isolated in fields of wheat and vineyards, which is one of the most beautiful in Tuscany. Your accommodation for the night is in very comfortable apartment (with a home-cooked dinner) in the small village that overlooks the abbey.
(12 kms, 2.5 hrs) |
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Today you climb up through vineyards and olive groves, to a beautifully retored medieval pilgrim town, a key point on the road to Rome, which is now a peaceful agricultural town and one of the most charming in the area. Despite its pedestrian centre, two beautiful Romansque churches and several beautiful gardens, which still remains relatively unvisited.
(12 kms, 3 hrs). |
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Today you follow parts of the medieval road down into the bare, rolling hills of the Val d'Orcia, with sweeping views across the valley to the forests and peaks of Mount Amiata before a short climb up to your base for the evening. This enchanting little town was the birth place of one of the more important 15th century popes, who had the modest village raised and then rebuilt in his honour, creating one of the gems of southern Tuscany, a fine example early Renaissance architecture. .
(12 kms, 4 hrs) |
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The last walk takes you through forests to Montepulciano. On the way you pass a tiny fortified village, perfect for lunch. Perched on a hill between the Orcia and Chianina valleys, Montepulciano was an ally of Florence in their relentless war against Siena, and was amply rewarded and has an extraordinary architectural heritage from this period.
(13 kms, 4 hrs). |
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After breakfast, you'll be dropped off at Chiusi, on the main Rome/Florence railway line. |

Contact Us
For more information on this tour or to make a booking, please get in touch with us.

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