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Walking Tour in Tuscany (5 days/4 nights - $1750 AUD per person) San Gimignano to Siena

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 Colle Val d'Elsa, which grew rich during the Middle Ages on its wool and glass industries (both of which are still thriving today), and the eerie fortress-village of Monteriggioni, the Sienese stronghold that made a powerful impression on Florentine Dante.
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 to Colle Val d'Elsa, entering the beautiful upper town via Antonio da Sangallo's impressive 16th century bastions, currently being restored.
The next day's walk takes you across the open fields that surround Colle, over the Elsa River and through woods to Monteriggioni, 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'.

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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? |
Accommodation 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 $1,750 per person (single supplement for a double room for single use $250)
(approx US $ 1575, SS $180 - 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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| Tuscany Walking Tour 3 Itinerary |
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A private vehicle will pick you up from either Florence airport or Florence railway station (Santa Maria Novella) 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. It 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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Todays walk takes you to Colle Val d'Elsa, another well-preserved medieval town that prospered trading on the Via Francigena. The walk leaves San Gimignano via vineyards and olive groves and a narrow, forested valley to Colle, passing through a landscape that has changed little since the Middle Ages.(13 kms, four hrs) |
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The walk 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 of Monteriggioni, which made such a deep impression on Dante. (18 kms, 4 hrs) |
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A walk that takes you from sleepy Monteriggione to Siena, the dynamic capital of southern Tuscany, through the forests, a 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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