Tuscany Walking and Wine

Our tour starts today in Pisa. Famous for its leaning tower and Campo del Miracoli, the Tuscan city is awash with sites that remain a testament to a time when Pisa was one of the Mediterranean's major maritime powers.

Our tour leader plans to meet everyone at the hotel for a welcome meeting today at 6.30pm and for those that wish, there is the chance to go out for dinner afterwards. If you miss the meeting, our tour leader will inform you of any essential information as soon as you catch up.

Airport transfers are not included on this tour but Pisa Airport is close to the centre of town, so getting to our hotel is easy. We recommend using the Pisa Mover - an automated shuttle train that departs from the airport to Pisa Central Station approximately every 10 minutes and takes just five minutes. Tickets cost €5. It's a 10-minute walk from Pisa Central Station to our hotel. If you'd prefer to take a taxi, there's a rank outside the terminal building. From the airport to our hotel, it should cost around €15-20.

We won't be climbing Pisa's leaning tower on our tour so if it's on your bucket list, or you'd like to explore Pisa in more depth, we recommend arriving earlier in the day or booking an additional night in the city pre-tour. Pisa is a compact city and is easy to navigate on foot.

This morning, we'll drive towards San Gimignano, parking our bus in the rolling countryside outside of the town. We'll set off on a hike along part of the Via Francigena cycle trail, (the Via Francigena is an ancient pilgrimage route running all the way from Canterbury to Rome), along a wide gravel 'white' track typical of the region, past vineyards and rural houses. The 14 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 hilltop 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'll have some free time to explore the town, have a relaxing lunch in one of the many cafes and perhaps walk up to the Torre Grossa, the tallest of the town's towers or visit the Duomo.

In the early afternoon, we'll head back on foot to the bus. It's a short drive to the first wine tasting of the holiday at the nearby Sovestro winery. The Failli family produce both the local San Gimignano Vernaccia white wine as well as Chianti reds. We then continue to our base for the next 2 nights, Castellina in Chianti, a country town with Etruscan and Roman origins. Castellina lies at an altitude of around 580m/1902ft in the heart of the Chianti Hills, an area famous for its wine.

Today's leisurely-grade 10 kilometre/6.2 mile walk is expected to take around three-and-a-half hours with a total ascent and descent during the course of the walk of 365 metres/1,197 feet.

We'll head out from our hotel after breakfast this morning, on an undulating route that takes us through the countryside south of Castellina past vineyards, fields and olive groves. Much of the trail is on 'strade bianchi', the rural backroads that wind their way across the countryside of Tuscany and Umbria, formed from white compacted limestone gravel. Our destination is the beautiful Castello La Leccia winery which produces organically cultivated Chianti Classico wines. We'll enjoy a tasting of Chianti wines and a light lunch of local cheeses and cold cuts.

We'll drive back to our hotel in the afternoon and the rest of the day is left free. You can explore the charming village of Castellina; the centre is just a few minutes walk from the hotel. Sit back and observe local life while enjoying an espresso or aperitivo at a pavement cafe, or maybe indulge your sweet tooth with a gelato. Our historic hotel has a lovely garden with a swimming pool (open in season), a great place to relax and read a book.

Today's moderate-grade 14-kilometre/8.7-mile walk is expected to take around four hours with a total ascent and descent during the course of the walk of 420 metres/1,378 feet.

Our final destination today is Pienza in southern Tuscany, but we'll stop for most of the day in the fabulous medieval city of Siena where our time is free to explore the Wednesday 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/328-foot 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 hilltop town and jewel of Renaissance architecture that UNESCO declared a World Heritage Site in 1996.

Our walk today makes a panoramic loop through the stunning countryside around Pienza and is known locally as the 'Gladiator hike' as scenes from that movie were filmed here. Along the route, we'll pass by the iconic Vitaleta chapel, a tiny, secluded building perched on a hill framed by cypress trees.

Pienza is known for its pecorino cheese and in the afternoon there's the option to enjoy a cheese tasting at the Armellini family's cheese shop in the town. Pecorino is produced from sheep of Sardinian stock, many farmers having relocated here from Sardinia in the 20th century.

Today's 10-kilometre/6.2-mile leisurely-grade walk is expected to take around three hours with a total descent and ascent of 350 metres/1,148 feet.

Today we'll drive from Pienza to San Quirico D'Orcia a beautiful town that lies along the Via Francigena pilgrimage route. We'll have time for a look around 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. We'll enjoy a picnic lunch along the trail.

Our final destination is the hilltop town of Montalcino located at just over 500 metres/1,640 feet above sea level. We have some free time to explore and the chance to enjoy a wine tasting of the famous Brunello di Montalcino wine.

Today's 13-kilometre/8-mile moderate-grade walk is expected to take around five hours with a total ascent of 523 metres/1,715 feet and descent of 383 metres/1,256 feet.

Leaving the rolling hills of southern Tuscany behind, we'll 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 tour 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 (outside only) 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 of the city.

The trip ends after breakfast this morning at our hotel in Florence.

There are no activities planned for today, so you're free to depart at any time. If you're departing later in the day, luggage storage facilities are available at our hotel.

If you'd like an airport transfer today, you'll need to depart from either Pisa Galileo Galilei International Airport (PSA) or Florence Peretola Airport (FLR). The transfer is provided by train or tram, our hotel is within a short walking distance from Florence Centrale Railway Station. If departing from Pisa Airport our tour leader will provide you with tickets for the train direct from Florence Centrale Railway Station to Pisa Centrale Station and then on to the airport on the Pisa Mover rail shuttle. The total journey time is around 90 minutes. If you're departing from Florence Airport you will be given a ticket for the T2 tram which runs direct from Florence Centrale Railway Station, a journey of around 20 minutes.