Arrive in Florence and instantly begin to take in the vibrant atmosphere of the Renaissance. Plan to get there early in the day to enjoy a mind-boggling 3.5-hour city walk to magnificent squares and the well-loved River Arno, a cultural circuit which -fittingly- starts and ends at Piazza della Signoria.

Zoom uphill on a 25-minute city bus ride to the village of Settignano, where your walk commences. And not just any walk, this one has you gazing out over lines of cypress trees, grey-green olive groves and Renaissance villas, while the whole city of Florence spreads out at your feet. Stroll through charming Fiesole and tour its intriguing Etruscan ruins, Roman amphitheatre and Franciscan monastery.

Challenge: 3/6 hours, 8/16 km, 345/565m ascent, 225/565m descent

Take your luggage and jump on a local bus or book a private transfer to Greve in Chianti, a rustic market village and the capital of this renowned wine-producing region. Check in at your hotel, just briefly, and head over to Le Cantine di Greve where you can sample over 50 different Chianti wines. Take advantage of the remaining daylight hours and amble through gorgeous scenery on your choice of two routes.

Walk A: Greve in Chianti loop via Uzzano
Hike north from Greve’s pretty main square and meld with the picture-perfect Chianti Classico landscape. Stroll past Villa Calcinaia through seemingly endless vineyards of local ‘aziende agricole’, the famous farms where prestigious Chianti wines are produced.

Walk B: Greve loop via Montefioralle
Explore wonderful woodlands with wild vegetation, elegant villas, verdant vineyards and olive groves. Trundle along past age-old abandoned farms, mysterious ruins and stately manors as you make your artistic way to the panoramic hamlet of Montefioralle.

Challenge: 2.5/3.5 hours, 11.4/10 km, 425/360m ascent, 450/355m descent

Set off on a circuit from Panzano, walking nearby hills and quintessential Chianti scenes in a dreamy landscape where forests alternate with vineyards and ancient Roman farmsteads.

Challenge: 4 hours, 11.7 km, 385m ascent, 385m descent

A short transfer takes you up to the highest of the Chianti hills, Monte San Michele. Hiking from Badiaccia, you make your way downhill through a forested valley inhabited by centuries-old chestnut trees. The stunning medieval hamlet of Volpaia awaits, nearly hidden amongst castles and vineyards. Pause at a fine ‘enoteca’ wine shop to tickle your tastebuds with a glass of red then press onward to reach Radda in Chianti.

Challenge: 5/3 hours, 14/12 km, 505m ascent, 670m descent

What a perfect plan! A quiet, relaxing day to bask in the Tuscan sun and go for a scenic walk through Radda’s old town centre. Wind along narrow lanes and wander up to Santa Maria Novella, with its simple facades and ornate interior. Linger among vineyard-covered slopes just outside town and treat yourself to a glass of Chianti Gallo Nero, THE local work of art.

Challenge: 5 hours, 15.8 km, 585m ascent, 585m descent

Grab your luggage and jump on a local bus or get in the taxi for a pre-arranged private transfer to marvellous Siena, famous for its ‘Palio’ horse race, held every two years in the most beautiful of shell-shaped squares, la Piazza del Campo. Of course the Duomo, too, is a must-see architectural treasure along with an array of imposing medieval palaces. History comes alive here, as you meander down narrow lanes in this fantastically preserved Italian gem.

Your self-guided walking holiday comes to an end after breakfast. Extra nights can be booked in Siena to allow time to explore the old city centre, exquisite museums, sumptuous galleries and infinite churches. A city which is perhaps best understood from above, with views from the tip top of the bell tower.