Tuscany 1 itinerary
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.
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)
Today you climb up through vineyards and olive groves, to a beautifully restored 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).
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 razed and then rebuilt in his honour, creating one of the gems of southern Tuscany, a fine example early Renaissance architecture. .
(12 kms, 4 hrs)
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).
After breakfast at 9.00 you'll be transfered to nearby Chiusi on the main Rome/Florence railway line.
Tuscany 1 Wine and Cooking Option Itinerary
This option is planned to precede the Tuscany 1 walk but can also be booked as a stand alone activity.
Morning: Pick up from Chiusi or Siena and transfer for a guided visit to the ‘monastery of the moon’, a magnificent 14th century monastery with famous frescos followed by a wine tasting in the monastery’s medieval cellars. Lunch: Lunch will be at a small family vineyard near Montalcino. Afternoon: visit to another excellent producer of Brunello di Montalcino, one of Italy’s great wines, and a visit to a local honey producer. Evening: Your accommodation is in a very good family-run 3 star hotel in the heart of Montalcino. The evening is free.
Morning: Cooking lesson: you will be driven to a nearby farm, where you’ll be taken through five courses (including home made pasta) by a local cook, with your English guide translating. Lunch: Lunch will be your morning’s work, accompanied by local wines. Afternoon: After lunch (around 2.30pm) you’ll have a number of options, that can be decided at the time, including: visit to a cheese maker; an easy walk through forest to a neighbouring town; and/or a visit to a local thermal springs that have been used since Etruscan times. Evening: the evening is free in lovely Montalcino.
Morning: This morning you can either start the first day of your Tuscany 1 itinerary or finish your visit and be transferred to either Siena or Chiusi.
Inclusions of wine / cooking option:
- two nights accommodation
- breakfast and two lunches
- private English-speaking guide and private vehicle throughout your visit
- 3 three wine tasting/vineyard visits
- transfer to and from Siena/Chiusi (on the main Rome-Florence train line)
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This 6 day walk can be personalised to meet your interests and dates.
- Five nights accommodation
- all breakfasts
- 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
$1840 b&b or $2100 with dinners included
Single supplement: $650
Montalcino Wine and Cooking Option - $990 per person
5% discount when 4 people or more book and deposit together.
"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."
– Bridget N, Tuscany 1 walkView all Testimonials ›
2. Central Italy: Tuscany 1, from Montalcino to Montepulciano FAQs
Find out a little more about the 2. Central Italy: Tuscany 1, from Montalcino to Montepulciano tour by reading some of our most frequently asked questions.View all FAQs ›