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The Hill-Top Towns of Tuscany

8 days/7 nights

Self Guided Walking Tour
Guide Price €1,495 per person (based on 2 adults sharing)

Discover Tuscany’s rich culture and timeless countryside, stay in hill-top towns, including atmospheric San Gimignano, and savour the famous wines and beauty of the Chianti hills, while walking self-guided from one hotel to the next while your luggage is transported.  

Highlights:
  • Intriguing Etruscan Volterra and fortified medieval San Gimignano
  • Explore hill- top villages and idyllic churches
  • A journey that embraces relaxed adventuring
  • Sample local vintage wines from San Gimignano
  • Enjoy the superb sights of Siena
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Itinerary

Day 1  Volterra  
Arrive in Volterra at any time.    

Day 2  Volterra  
Enjoy a short introductory walk to explore the soft rolling hills south of the town, by first following the route of an old rack-railway, before heading uphill across an evocative landscape that offers a striking profile of hill-top Volterra as you ascend gradually back to the town. Afterwards, spend some time exploring splendid Volterra.  

Day 3  Volterra to San Gimignano  
After a short transfer, you follow pleasant tracks and strade bianche across a couple of small valleys, through woodland and agricultural land as well as the village of San Donato. You pass numerous isolated farmsteads, once occupied by families of share-croppers, and enjoy fine views across gently rolling hills to your destination, San Gimignano.  

Day 4  San Gimignano  
For a good introduction to medieval San Gimignano, stroll around the town walls and look down on the charming streets lined with ancient houses and palaces. For those wishing to walk a little further, take a circular route in the glorious countryside, which provides fantastic views towards the town's imposing towers.  

Day 5  San Gimignano to Colle Val d'Elsa  
This beautiful walk takes you through much softer, archetypal Tuscan landscapes of olive groves and vineyards and across the small River Foci to the historic upper part of Colle Val d'Elsa, a fascinating town surrounded by ramparts.  

Day 6  Colle Val d'Elsa to Siena  
After a transfer to the fortified hamlet of Monteriggioni, you walk along a section of the Via Francigena, the ancient pilgrims' route between Canterbury and Rome, to arrive in Siena.  

Days 7-8   Siena  
Today is devoted to sightseeing. The centre of Sienese life is the delightful Campo, a piazza bordered on one side by the Palazzo Pubblico, which houses some splendid frescoes, including Lorenzetti's Effects of Good and Bad Government, and is topped by the Mangia Tower, which offers a superb panorama of the city. The cathedral is also well worth a visit (among its masterpieces are works by Jacopo della Quercia and Donatello), as are the Museo dell'Opera del Duomo and the Pinacoteca. Your self guided walking tour ends on day 8, depart at any time.  

Departs: Frequent departures, Apr – Jun & Aug - Nov  

Price & Inclusions

Guide Price €1,495 per person (based on 2 adults sharing)

Inclusions
  • 7 nights hotel accommodation
  • Luggage transfers between overnight stays
  • 7 breakfasts & 3 dinners
Not Included
  • International flights
New offers every day!

We negotiate new offers daily from discounted flights, tours and vehicle hire to free upgrades, added value and unique inclusions. Please call for our latest offers.

The tour itinerary, inclusions and departures are based on travel from 01/10/2024 to 31/12/2025. Guide prices are based on twn/dbl share, are subject to availability and may vary by departure date. For travel outside of these dates, the itinerary and inclusions may vary to that shown above - please ask for details.
Offers are subject to availability and restrictions may apply.

Flights

As we can offer you such a flexible choice of flights, we don't include international airfares with our tour prices. The price you pay will be determined by the time of year you travel, your departure airport, airline and availability.

Your Trailfinders Travel Consultant will be able to find the best flights to suit you and your choice of tour. Contact us for our latest flight offers or take a look at our flights pages for a general idea of prices.

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