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The Hill-Top Towns of Tuscany

Landscapes immortalised by artists

Holiday information
Nights: 7
Grade: 1-2
Terrain: tracks and strade bianche (unmade roads) across gently rolling hills of vineyards, olive groves and woodland
Hotels: three 3-star hotels; one 4-star hotel
Meals: breakfast each day, dinner on 2 nights
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Extend your stay

If you are flying via Pisa, why not stop over at one of our hotels (please call for details); or experience Florence, Italy's greatest art city, with two nights at the superior 3-star Il Guelfo Bianco.
Alternatively, you can combine either version of this holiday with our Tuscan Heartland walk to make a superb fortnight-long holiday.
  • self-guided hotel-to-hotel walking, luggage transported
  • discover Tuscany’s rich culture and timeless countryside
  • the famous wines and beauty of the Chianti hills
  • stay in atmospheric San Gimignano


Nestling between the great art cities of Florence, Siena and Pisa, the Chianti hills are as famed for their beauty as for their dark red wines. Hill-top villages crown the rolling landscapes, and idyllic churches are dotted along the quiet paths. An extraordinary sense of history pervades the region, from Siena’s wide Campo to the Etruscan town of Volterra.

We emerged into open country, with fresh, luminous greens and yellows, geometric vines, silvery olives and Tuscany's quintessential punctuation marks - the cypress trees.
     
Mail on Sunday

This walk takes you from Volterra through the Chianti vineyards and San Gimignano to the Sienese hills and magnificent Siena itself. The joy of the holiday is to feel the timelessness of the Tuscan countryside, and to discover the landscapes immortalised in the works of some of the world’s greatest artists.
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