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The Hill-Top Towns of Tuscany

A stroll through history

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. 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.

Nights: 7 (8 if you opt for the Deluxe Option which includes superior hotels in Colle Val d'Elsa, where you spend two nights, and Siena)
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 3 nights
Climate: average temperatures of this warm, sunny region range from 15°C in May to 22°C in July and August.

Volterra

San Gimignano

Near Volterra

Colle Val d'Elsa

Old house in Colle Val d'Elsa

Siena's Campo

Starting point: Hotel San Lino (3*), Volterra. Located in the western part of the town, this hotel is a good base from which to explore Volterra. There is a good-sized outdoor pool in which to relax at the end of the day. Take your pick of the local restaurants using our recommendations as a guide (pay locally).

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.

Accommodation: Hotel San Lino, as above.

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. (13km, 3.5hrs)

Accommodation: Hotel Bel Soggiorno (3*), San Gimignano. The Gigli family have owned this favourite hotel for several generations, and have created a friendly, welcoming atmosphere. Centrally located within the town, the hotel nevertheless offers some fine views across the vineyards below the town, some of the best of which are enjoyed by the acclaimed restaurant (closed Wednesdays), which draws a loyal local following. We book a panoramic bedroom for you when available.

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 surrounding countryside. If you prefer another walk, we suggest a gentle ridge walk to the north and east of the town that offers uninterrupted views of the glorious countryside and San Gimignano's towers. (10km, 3hrs)

Accommodation: Hotel Bel Soggiorno, as above.

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. (13km, 4hrs)

Accommodation: Vecchia Cartiera (3*), Colle Val d'Elsa. A comfortable hotel built on the site of an old paper mill. There is a spacious lounge in which to relax. Take your pick of the local restaurants using our recommendations as a guide (pay locally).
Upgrade option: Relais della Rovere (4*), Colle Val d'Elsa. Located on the outskirts, this elegant hotel has been converted from a former cardinal's residence and is a stylish blend of ancient and modern, with individually decorated bedrooms. Prices for our upgrade option include 2 nights here (bed and breakfast), so that you can make the most of the shaded gardens. Alternatively, you could enjoy a walk from the town which starts with a bus ride to a fortified village (pay locally) then returns to Colle Val d'Elsa along part of the trail followed by pilgrims travelling to Rome from France. (13.5km, 5hrs)

Day 5: a long but fine walk which, after a short transfer, leads along ancient stone paths through the mysterious woodland of Monte Maggio, criss-crossed by mule tracks. You descend to the hamlet and chapel of Funghaia, and from here cross farmland to the outskirts of Siena. (18km, 6.5hrs)

Accommodation: Hotel Garden (4*), Siena. Created from the former summer home of an aristocratic family, the Hotel Garden stands on a hill to the north-west of the old town within its own attractive, shady gardens (complete with outdoor pool) and is surrounded by vineyards and olive groves. We include dinner here on your first night. The centre of Siena is walkable from here but you may prefer to take a bus (pay locally).
Upgrade option: Palazzo Ravizza (4*), Siena. This Renaissance mansion makes a wonderful base for exploration of Siena, located as it is in a quiet square just a few minutes' walk from the historic centre. The interior retains many grand original features, while outside the flower-filled gardens look out on to the countryside.

Day 6: your last day is again devoted to sightseeing. The delightful Campo is the centre of Sienese life, a plaza 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.

Accommodation: Hotel Garden, as above.

Walking chart: the chart gives the distance and an approximation of the ascents and descents involved each day. If comparing holidays, please note the scale of each chart as this can differ.

Recommendations for extra nights: the Hotel Garden is a good choice to give you extra time to discover beautiful Siena.

Extensions: If you are flying via Pisa, experience Florence, Italy's greates art city, with 2 nights at the superior 3* hotel Il Guelfo Bianco.

Other information: if you would like to see the brochure page, you can download this (and the pages for any other holidays you are interested in) by using our brochure creation system.

Similar holidays: A Stroll through History (grade 1-2), From the Tuscan Hills to the Sea (grade 1-2), The Tuscan Heartland (grade 2), Sunflowers & Abbeys (grade 1-2), From the Tarn to the Aveyron (grade 1-2), Villages of the Dordogne (grade 1-2), Paths to Rocamadour (grade 1-2)

Prices & travel 2008:

Recommended destination airports: Pisa
Latest flight arrival time: flexible if purchasing direct taxi transfer from Pisa
Earliest flight departure time: 1200
*Connecting travel: taxi from Pisa & rail back (out 1h15/home 2h55) £45pp;
Extra nights can be booked at any hotel
Start: any day
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