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.

Meals included: None
Accommodation: Hotel David
Located on the southern side of 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.

Begin with a private transfer to the wine town of Greve in Chianti where its charming piazza is the starting point for today’s walk. Leaving the town on foot, climb to the hilltop hamlet of Montefioralle. Once a significant stronghold during the 13th-century Sienese-Florentine conflict, take time to explore the cavern of streets or enjoy lunch in one of the rustic restaurants. Return to Greve along a typical white gravel road, known locally as ‘Strade Bianche’. Tonight you will dine at your family-run hotel.

Walk: 9km
Ascent: 350m
Descent: 350m
Meals included: Breakfast
Accommodation: Albergo Chianti
Owned by the Buys family of the Le Maurcy wine cellar, this 3* hotel is located just off the main piazza. Simple, comfortable en-suite rooms provide a good night’s sleep and the hotel restaurant is a favourite with locals and tourists alike. If you arrive in good time you can take a dip in the hotel pool or take advantage of the bar and terrace area.

After a short taxi transfer deep into the Chianti Winelands 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 Guisto 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 Chainti.

Walk: 12km
Ascent: 350m
Descent: 500m
Meals included: Breakfast
Accommodation: Cavarichino
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 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 s 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 to 15km
Ascent: 660m or 400m
Descent: 600m or 250m
Meals included: Breakfast
Accommodation: Cavarichino

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 in Lecchi in Chianti, 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
Round off your week with a 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.

Depending on your onward travel arrangements, we’d suggest an early morning stroll around the streets of Siena and Piazza del Campo before the buzz of the crowds descend into the streets.

Meals included: Breakfast