The Cradle of the Renaissance, Florence is a city of fine art, fashion and exceptional architecture. Many of Florence’s sights need little introduction. Stroll across the medieval Ponte Vecchio bridge and head to the world-famous Uffizi art gallery where the masterpieces of Leonardo da Vinci and Raphael hang. Visit the Galleria dell’Accademia to see Michelangelo’s statue of David and walk through cobbled streets to Piazza del Duomo to marvel at the exquisite designs of Brunelleschi.

Accommodation: Hotel David
Located on the southern side the River Arno, the hotel is set in a 19th-century building only a couple of minutes’ walk from the Arno River. Classically furnished rooms have a free mini-bar and breakfast is well known for its selection of homemade pastries. The historic centre is a 5-minute bus journey, or you can enjoy a 20-minute riverside walk to Ponte Vecchio and cross into the splendour of Florence.

Transfer deep into the Chianti Winelands to begin your walk on a forested trail to the fortified village of Volpaia, home of the revered Volpaia red wine (a must to sample while you are here). Steeped in winemaking tradition, the town has been producing wine since the late 12th century. Beyond Volpaia, the trail follows typical ‘white roads’ lined with cypress trees as you ascend to the hilltop church of Santa Maria Novella (which has retained its original Romanesque structure). The trail rolls on through vineyards to the hilltop town of Radda in Chianti, one of the most celebrated wine towns of the Chianti region.

Walk: 13.5km
Ascent: 500m
Descent: 660m
Meals included: Breakfast
Accommodation: Hotel Palazzo San Niccolo

An elegant 4* hotel in Radda’s the Ciacci and Palagi. Within the building is a peaceful courtyard where you can relax with a glass of local Chianti or head into the garden to soak up the Tuscan sun. Rooms have been classically designed, in keeping with the history of the building. Before you leave this hotel, do take time to visit the small sitting room with an incredibly well-preserved fresco that is said to be a symbol of unity between the 2 families.

A gentle start begins with a descent southwards to your destination today, Gaiole in Chianti. Walk through wooded valleys, vineyards and olive groves. Enjoy rambling through picture-postcard Tuscan landscapes, passing through the hamlets of San Giusto in Salcio and Adine. Descend into the sleepy streets of Gaiole in Chianti where you will spend the next two nights and have the opportunity to learn more of the Chianti wine production and signature Tuscan dishes of Gaiole in Chianti.

Walk: 12km
Ascent: 350m
Descent: 500m
Meals included: Breakfast
Accommodation: Cavarchino

A restored farmhouse on the outskirts of Gaiole, Cavarchino is a charming family-run bed and breakfast. On arrival, you can relax in the gardens or take a dip in the pool before strolling into the Gaiole centre for dinner. Your host, Irene is always happy to help out with any questions or assistance you might need whilst in Gaiole.

Walk through the medieval streets of Gaiole and into the rich Tuscan countryside as the route climbs to Castello di San Donato in Perano, a cluster of well-preserved 10th-century houses. Continue on through woodland trails which will see you arrive at the hamlet of Badia a Coltibuono. For over 1000 years the Coltibuono farm has been producing wines, olive oils and has been a great spot for lunch before walking to the hilltop village of Montegrossi. A gentle but straightforward ramble descends back to the tranquillity of Gaiole and your hotel.

Walk: 19.5km or 15km
Ascent: 660m or 400m
Descent: 600m or 250m
Meals included: Breakfast
Accommodation: Cavarchino

Follow trails across a rolling landscape of olive groves and vineyards of Castelle di Meteo where since 1256 much of the land has been dedicated to producing this prestigious wine. Onwards from Castelle, much of the land is cloaked in oak woods and you might be lucky enough to spot an elusive deer en-route. Arriving into Lecchi Chainti, little has changed in this delightful town since the 12th century. From Lecchi, a private transfer will take you onwards to Siena and a visit to Piazza del Campo, one of the largest medieval squares in the world.

Walk: 11km
Ascent: 350m
Descent: 300m
Meals included: Breakfast
Accommodation: Hotel Chiusarelli

Spend the night in a typical neoclassical villa dating back to the 1870s. Located in the historical centre, several years ago the hotel was refurbished to a traditional Sienese house, complete with large, beautiful preserved frescos. A charming and fitting end to your walking trip.

Transfer by private transport to Buonconvento. Wander along its historical centre, Via Soccini. Continue walking through the iconic Sienese landscapes, along trails and the strade bianche (white roads) lined with the towering and elegant cypress trees and through the Brunello vineyards that grow Sangiovese grapes for world-class wine. The day ends with a climb up to the 14th-century hill town of Montalcino, nestled amongst the hills of the Val d’Orcia.

Walk: 18.5km
Ascent: 540m
Descent: 3170m
Meals included: Breakfast
Accommodation: Hotel dei Capitani

Dating back to the middle ages, Hotel dei Capitani is believed to have been used as a refuge for Sienese people fleeing the Florentine army. The hotel pool boasts splendid views across Val d’Orcia and Val d’Arbia, which can also be viewed from your room. All rooms have a typical Tuscan decor.

South of Montalcino, an easy-going route, rolls through classic Tuscan landscapes. Just before reaching the delightful town of Castelnuovo dell’Abate, take time to visit the Romanesque Abbey of Sant’Antimo, dating back to the 8th century. The monks at the abbey still meet seven times a day, so you may be fortunate to hear the medieval Gregorian chants. Above the abbey, the village of Castelnuovo is a superb stop for lunch. Later in the afternoon, a private transfer will take you on to the Roman spa town of Bagno Vignoni.

Walk: 12km
Ascent: 280m
Descent: 470m
Meals included: Breakfast
Accommodation: La Locanda Loggiato

Sisters Barbara and Sabrina have been welcoming guests to Bagno Vignoni for almost 20 years. Their 14th-century property has been lovingly restored with all en-suite rooms featuring terracotta flooring and traditional wooden beams. A place of relaxation, not all bedrooms have wi-fi (but it is available in communal areas). La Locanda is the perfect environment to relax in after a visit to the thermal baths just a few minutes away in the main piazza.

Begin the day with a rewarding stretch of uphill to Vignoni Alto, complete with its own fortress tower. Onto San Quirico d’Orcia, the route gently descends through rich agricultural lands. Located on the Via Francigena pilgrim route, in medieval times the beautifully preserved San Quirico d’Orcia was of significant strategic importance, linking Europe with Rome. Do make time to explore the town and enjoy lunch in one of the many rustic restaurants. Continuing onto the hilltop town of Pienza be sure to try the local Pecorino cheese made from sheep’s milk.

Walk: 19.5km or 15km
Ascent: 660m or 400m
Descent: 600m or 250m
Meals included: Breakfast
Accommodation: Hotel La Valle

Within a couple of minutes of Pienza’s historic centre, the hotel occupies a typical Tuscany stone building. Complete with a roof garden, panoramic breakfast room, bar and en-suite rooms, you can enjoy breakfast on the terrace with views that stretch out over golden wheat fields and vineyards.

Set across a rolling hilltop, the elegant town of Montepulciano boasts one of Tuscany’s oldest wine producers; Vino Nobile. Walk via the hamlet of Monticchiello through a patchwork of rolling fields as the trail climbs up to Montepulciano. Explore the labyrinth of cobbled streets, lined with elegant Renaissance palaces, former homes of nobility and hidden piazzas. At the heart of the town is the Piazza Grande, a wonderful setting to taste the rich variety of Montepulciano wines. In the evening it’s worth strolling out to the edge of the old town to see the sunset over the Val d’Orcia.

Walk: 15km
Ascent: 550m
Descent: 450m
Meals included: Breakfast
Accommodation: Hotel II Rondo

Located outside the lively town centre, the family-run Hotel II Rondo is tucked away in a peaceful corner of Montepulciano. After a day of walking and exploring, relax in the impeccably maintained gardens. In keeping with the period of the building, rooms have been decorated to an 18th-century style.

From Montepulciano the nearby train station, Chiusi Chianciano Terme has regular connections through to Florence, Pisa and Siena. You may also have time to further explore the streets of Montepulciano or relax in the garden of your hotel.

Meals included: Breakfast