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.

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. Breakfast only is included leaving you free to take your pick of the many local restaurants(pay locally).

Day 1: On your first day 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 much-loved 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, which draws a loyal local following and where dinner is included, except Wednesday, when you are free to dine elsewhere.

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, 2h30m)

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, 3h30m)

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 or enjoy a panoramic circular walk. (13.5km, 3h45m)

Day 5: after a taxi 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. (16km, 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 an outdoor pool) and with views to the surrounding vineyards and olive groves in the near nistance. We include superior rooms. 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 (upgrade to a superior room from £20pp/n).

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.

Accommodation: Hotel Garden, as above.

The walking holiday is Grade 1-2. Generally easy walking with some ascents/descents and occasional longer days upto 18km.