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Walking Tour in Tuscany - San Gimignano to Siena
(5 days/4 nights - $1,990 AUD per person)
Siena view

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This walking tour in Tuscany can be personalised to meet your interests and travel dates.
Starting with a transfer in a private vehicle from Florence to San Gimignano, this walking tour in Tuscany passes through the heart of medieval Tuscany, starting in the marvelous towered town of San Gimignano and finishing at the dynamic regional capital, Siena. On the way you will visit a town strategically perched above the Elsa River which grew rich during the Middle Ages on its wool and glass industries (both of which are still thriving today), and an eerie fortress-village, which was the Sienese stronghold guarding their northern border against the implacable Florentine enemies and was written about in Dante's Inferno.
The route follows the contours of the Elsa River valley, (the Val d'Elsa), taking you through a range of landscapes. Leaving San Gimignano by the gates, the walk passes through the vineyards and olive groves that surround the town. It follows small streams along winding valleys entering your base for the night via Antonio da Sangallo's impressive 16th century bastions, recently restored.
The next day's walk takes you across the open wheat fields, across the Elsa River and through woods to a medieval fortress village (a ring of imposing walls containing a handful of houses), where you'll stay in a very comfortable four star hotel. The final day's walk goes crosses a mountainous district, skirting through thick oak and birch forests, and climbing up to the walled city of Siena, 'the most perfectly preserved medieval city in Europe'.
"A short note to say our walking trip in Tuscany was fantastic. A big thank you. Words cannot convey how outstanding the accommodation was, the food, the people and the walks.... We are still excited and can't stop taking about the beauty of the vineyards, the landscape, the wild flowers, the tranquillity of the place - the whole experience was breathtaking."
HG, 2009

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What's included in this walk? |
- four nights accommodation
- all breakfasts and dinners
- recommendations for lunch
- reading lists and historical and cultural notes
- maps and detailed walking instructions
- daily transfers of baggage between hotels
- pick-up from Florence railway station or Florence airport and transfer to San Gimignano on Day 1
- 24 hour backup from local manager
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How hard are the walks? |
Grade 2 Walk - Good paths, straightforward orientation, several walks longer than 15 kms, no long climbs.
This generally follows well marked, gravel roads, over undulating land without any steep climbs, however, a couple of the walks are quite long.

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What's the accommodation like? |
ccommodation is in comfortable, family-run three-star and four-star hotels. Costings are calculated on two people sharing a double room. All rooms have an en suite bathroom.


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Tour Cost: |
AUD $1,990 per person (single supplement for a double room for single use $350)
(approx US $1,790, SS $300 - subject to daily exchange rates)
AUD $1,770 per person (No Dinners Option)
(approx US $1,590 - subject to daily exchange rates) |

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


Hilltop village

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Arcades, Tuscany

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Chingiale, Tuscany

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Olive groves

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Palazzo Pubblico, Siena

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Piazza del Campo, Siena.

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A private vehicle will pick you up from Florence and take you to your hotel in San Gimgnano, a walled medieval town, famous for its towers, which grew rich as a trading town on the most important route to Rome in the Middle Ages and which retains most of its treasures from this era. In the afternoon there is a short loop walk through the celebrated Vernaccia vineyards with wonderful views over San Gimignano's famous skyline before returning to San Gimignano.
(8 kms, 2 hrs) |
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Today's walk takes you to another well-preserved medieval town that prospered trading on the Via Francigena. The walk leaves San Gimignano via vineyards and olive groves before following a narrow, forested valley. It passes through a landscape that has changed little since the Middle Ages.
(13 kms, four hrs) |
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The walk this morning picks up the original route of the Via Francigena, crossing undulating farmlands and passing hamlets, castles and a fine Romanesque abbey before arriving at the tiny walled gem, a restored castle, a ring of high walls enclosing a precious collection of houses, gardens and palazzi, which made such a deep impression on Dante.
(18 kms, 4 hrs) |
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The walk today takes you from this sleepy village to Siena, the dynamic capital of southern Tuscany, through forests and the sparsely populated range of hills that once protected Siena's northern frontier from their mortal enemies in Florence. Siena is a fascinating city that maintains much of the aspect and atmosphere of its heyday in the 14th and 15th centuries. A city rich in art and history, grown up around the Campo, its famous scalloped-shaped central piazza, Siena is a wonderful place to explore or simply while away time, sipping an aperitivo and watching the colourful life pass by.
(14 kms, 5 hrs) |
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Breakfast at your hotel. Siena is connected by rail and bus to Florence, from where you can continue your holiday. |
Contact Us
For more information on this tour or to make a booking, please get in touch with us.

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