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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 & one 4-star hotel
Meals: 2 dinners, 7 breakfasts
Extend your stay
This combines well with our Essence of Tuscany walk to make a superb fortnight-long holiday.
Starting point:

Hotel San Lino in Volterra for your first two nights.

Day 1

Your first day is free to explore splendid Volterra. This atmospheric town boasts substantial Etruscan and Roman remains, as well as several museums and an art gallery. Stroll along Via Ricciarelli, where there are some fine tower houses, and visit one of the workshops where they still work alabaster. Take time, too, to admire the views of the volcanic hills surrounding the town from the ancient ramparts. Alternatively, we suggest a short introdcutory walk to explore the soft rolling hills south of town, by first following the old rack-railway that ran from Saline to Volterra from 1912-1958, before heading uphill across an evocative landscape that offers a striking profile of hilltop Volterra as you ascend gradually back to town. (9km, 3hrs)

Day 2

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, which boasts a lovely church. You pass numerous isolated poderi (farmsteads), once occupied by families of share-croppers who grew wheat, olives and grapes, and enjoy fine views across gently rolling hills to your destination, San Gimignano, where you have two nights at the Hotel Bel Soggiorno. (13km, 3.5hrs)

Day 3

Spend your day discovering medieval San Gimignano, strolling along its charming streets lined with ancient houses and palaces. Only thirteen of the town's seventy towers remain today. On clear days it is well worth climbing the tallest of these, the tower belonging to the Palazzo del Popolo (pay locally), for splendid views of the area. For a longer walk, we recommend striking out into the countryside for a glorious circular route, which provides fantastic views over the town's imposing towers and is dedicated to the Vernaccia wines. (17km, 4hrs)

Day 4

A beautiful walk that takes you through much softer, archetypal Tuscan landscapes of olive groves and vineyards and across the small River Foci to Colle Val d'Elsa. You arrive via the upper town, then descend the ramparts to the lower part. Take time to explore this fascinating town before dinner. Your hotel for the night is the Vecchia Cartiera. (13km, 4hrs)

Day 5

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 for your final two nights at the Hotel Garden. (16km, 5hrs) 

Day 6

Your last day is again devoted to sightseeing. The delightful Campo is the centre of Sienese life, 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.

Stay over in Florence or Pisa

If you are flying via Pisa, why not stop over at one of our hotels; or experience Florence, Italy’s greatest art city, with two nights at the superior 3-star Il Guelfo Bianco. 

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 Grade 1-2 Walk
Local Map
 Walking Chart
Walking Chart:The Hill-Top Towns of Tuscany This is an approximation only. If comparing holidays, please note the scale of the chart as this can differ.
Upgrade option:
Our 8-night deluxe version is that little bit more special. With 2 nights in Colle Val d'Elsa, you can enjoy a circular walk while staying in a 4 star hotel, plus upgrading in Siena, too.