Detailed Day Wise Itinerary

• Day : 1  Join trip Pisa airport

  Joining the trip in Pisa today, we drive to our hotel in Castellina in Chianti, a country town with Etruscan and Roman origins. Castellina lies at an altitude of around 580m in the heart of the Chianti Hills, an area famous for its wine.

• Day : 2  Chianti country

  After breakfast we drive close to the town of Volpaia, near to Radda in Chianti. Our walk heads out from the small chapel of Santa Maria Novella and slowly climbs through vineyards and along marked trails up into the hills of Chianti to the picture perfect village of Volpaia. We then follow local village paths and old drovers' roads, cutting through the vineyards and fields of the villa of Castelvecchi. Finally, we descend back to Santa Maria Novella for a well-earned rest in the olive groves of the church and our picnic lunch. A short bus ride takes us to Radda for some time to explore and look around and perhaps have a gelato. On our way back to Castellina we will stop at the Rocca della Macie wine estate for a tour and tasting of the famous Chianti Classico. Today's seven kilometre walk is expected to take around four hours with a total ascent and descent of 150 metres.

• Day : 3  San Gimignano

  This morning we drive towards San Gimignano before setting off on foot along part of the Via Francigena (an ancient pilgrimage route running all the way from Canterbury to Rome) along a wide gravel track past vineyards and rural houses. The thirteen medieval towers of San Gimignano are often in sight in the near distance. San Gimignano is a beautifully preserved example of a classic Tuscan medieval town. It prospered during the 12th and 13th centuries, until a combination of local aristocratic rivalry and the arrival of the Black death devastated trade. We will have some free time to explore the town, have a relaxing lunch in one of many cafes and perhaps walk up to the Torre Grossa, or visit the Duomo. After lunch we plan to visit the Sovestro winery for a tasting of some of the local San Gimignano white wine. We then continue to Monteriggioni, a beautifully preserved fortified hill-top village, where we can walk around the walls before driving back to Castellina later this afternoon. Today's gently undulating ten kilometre walk is expected to take around three-and-a-half hours.

• Day : 4  Visit medieval Siena

  Our final destination today is Pienza in southern Tuscany, but we will stop for most of the day in the fabulous medieval city of Siena where our time is free to explore the market and other sights. With its magnificent Gothic architecture, Siena was once a rival to Florence in power and trade, the city controlled the trade routes between France and Rome, as well as the southern Tuscan wool industry. Today it stands as a classic Italian city, with its magnificent central square, Il Campo, and the awe inspiring grandeur of the Duomo overlooking the Via di Citta. The city centre is traffic-free, making it ideal to wander around on foot, soaking up the many intriguing sights. The focal point is the Piazza del Campo, a semi-circular area surrounded by ancient buildings, and overlooked by a 100 metre bell tower, the Torre del Mangia. The Piazza is also used for a horse race twice a year - the famous Palio, when horses and their riders hurtle dangerously around the square to the delight of the crowds. Pienza, our base for the next three nights, is a classic hill-top town and jewel of Renaissance architecture that UNESCO declared a World Heritage Site in 1996.

• Day : 5  Montepulciano via Montichiello

  Our walk today heads downhill from Pienza on typical 'strade bianche', the white gravel roads of Tuscany. We head towards the village of Montichiello, a lovely medieval walled village where we will have a well earned break and admire one of the most famous cypress tree avenues in the whole of Tuscany (and the one on most of the postcards!) Retracing our steps a little way downhill, we pick up our trail heading past vineyards, enjoying some enchanting views across the surrounding countryside as we make our way towards the temple of San Biagio on the hillside below the town of Montepulciano. Founded by Antonio Sangallo the Elder in the 16th century, this glorious church was, at the time, the largest outside of Rome and is considered by many to be one of the finest Renaissance buildings in Italy. Continuing up the hill into the town, we head via the Piazza Grande, Montepulciano's flamboyant main square. Perched on a 605 m high limestone ridge and encircled by Renaissance-era walls and fortifications, Montepulciano is a major producer of food and drink; renowned for its pork, cheese, 'pici' pasta, lentils, and honey and not least its wine. Connoisseurs consider its Vino Nobile among Italy's best. Before heading back to Pienza by local bus, we will have time to explore some of the underground cellars of Montepulciano with the option of enjoying a wine tasting. Today's 12 kilometre walk is expected to take around four-and-a-half hours with a total ascent of 350 metres.

• Day : 6  Hike in the Val D'Orcia to hill-top Montalcino

  Today we drive from Pienza to San Quirico along a panoramic road where some of the scenes from the film 'Gladiator' were filmed. San Quirico D'Orcia is a beautiful town that lies along the Via Francigena pilgrimage route and we will have some time here, before we set out on our walk. Descending from the town we cross the Asso river and follow undulating trails with wide open views of the classic Val D'Orcia. Vineyards surround us and the towers of Siena are visible on the Horizon. Our final destination is the hill-top town of Montalcino located at just over 500m. We have some free time to explore and the chance to enjoy a wine tasting of the famous Brunello di Montalcino wine. Today's 12 kilometre walk is expected to take around five hours with a total ascent of 450 metres.

• Day : 7  Florence; orientation walk

  Leaving the rolling hills of southern Tuscany behind we head for our final destination of the holiday, the fabulous city of Florence. The spiritual home of the Renaissance, Florence is considered by many to be one of the most beautiful cities in Italy. On arrival our leader will take us out on an orientation walk with the rest of the day left free to explore further. Highlights include the Ponte Vecchio, the oldest and most famous bridge in Florence and the only one that was not demolished during the German retreat of 1944 and the Cathedral of Santa Maria del Fiore with its giant dome that dominates the city skyline. Early evening is the perfect time to walk up to the Piazzale Michaelangelo for a great view over the city.

• Day : 8  Trip ends in Florence

  The trip ends this morning after breakfast in Florence. If you are flying from Pisa Airport today,