Here we whisk you away on three scenic drives in Tuscany. Take it slowly, pack the camera, and meander your way through stunning panoramas and picture perfect views. And believe us, you’ll take a lot of pictures.

For best results start early in the morning to enjoy the magical light. Late afternoon is good too, so be prepared catch a view of the sun slipping behind the cypress trees. And if you’re travelling in the Summer months, these times make sense as you’ll avoid the hottest hours of the day.

scenic drives in tuscany
Image by Linda A. from Pixabay

The Chiantigiana. Endless vineyards and ancient castles

The SR222 ‘Chiantigiana road’ winds south from Florence to Siena. It’s probably the most famous of all scenic drives in Tuscany. And definitely one of the best ways to sample the beauty of Tuscany’s countryside. At the end of a day’s driving, you can taste some of the wonderful wines produced in the region. But for now let’s keep our eyes on the road.

Peaceful scenery is your companion on the drive from Greve in Chianti, the gateway to the Chianti area, to Panzano. The show carries on along the way to Castellina in Chianti, where the winding road embraces perfectly combed vineyards and silvery olive groves. Here we are at the heart of the Chianti Classico area, where wine and olive oil have been devoutly produced for hundreds of years. Ancient castles and beautifully restored farmhouses dot the countryside, often converted into agriturismi that offer accommodation and wine tasting.

BOOK YOUR CHIANTI CLASSICO E-BIKE TOUR => Explore the Chianti hills, visit a Medieval castle, taste some delicious wine!

=>8 Inspiring Places in Tuscany that’ll Spark your Imagination!

chianti italy

From Castellina take the SR429 to Radda in Chianti, the most scenic of all Chianti towns. Then go back to Panzano via the SP2bis, a lovely road that spirals through more vineyard and ancient woods.

Detour: visit the small Medieval hamlet of Montefioralle (4 km. above Greve in Chianti) for pure picturesque.

1 day:  Florence-Radda in Chianti (roundtrip: 100 km.)

Planning: For a more detailed version of this itinerary, check out our Chianti road trip.

=> Planning a trip to Tuscany’s wine region? Check out the best places to go in the Chianti.

Val d’Orcia. One of the top scenic drives in Tuscany

The Val d’Orcia is an area south of Siena, famous for its classic landscapes that have graced many a postcard. It’s an iconic side of Tuscany that has been seen all around the world. As countryside goes, it’s probably the most idyllic scenery you can imagine, and one of the highlights of the region.

Soft rolling hills, wheat fields that turn bright green in Spring and an intense yellow in Summer, and the occasional cypress tree, make the view just perfect. So perfect it is a UNESCO protected panorama. If you can tear yourself away from the view, carry on to the next stage.


From Siena take the SR2 to Buonconvento and the sleepy town of San Quirico d’Orcia with its splendid early Romanesque church . From there turn left onto the SP146 to Pienza and Montepulciano, arguably the most attractive towns of the Val d’Orcia. This is where the real spectacle begins.

A relaxed drive along the SP146 rewards you with some of the most spectacular views over the Val d’Orcia countryside. Take it easy, and stop when you can for a photo call. Things get quite special around sunset, as the trees cast shadows over the landscape and the setting sun turns the valleys deep shades of ochre and pink.

Useful tips to Plan your road trip to Tuscany.

val d'orcia
Vitaleta Chapel – Image by alefolsom from Pixabay

Not to miss: On the SS146, halfway between San Quirico and Pienza, you’ll spot the Vitaleta Chapel on your right, a small church flanked by cypresses crowing the hill. This must be the most photographed spots in all of Tuscany.

Detour: visit tiny Monticchiello (a few kilometres south of Pienza on the SP88) for more awe-inspiring views and a pretty stone square.

1 day – Siena-Montepulciano (roundtrip 140 km.)

=> For the perfect day in the Val d’Orcia, check out our driving itineray in Val d’Orcia.

Central Tuscany. A taste of classic Tuscany in a day

This itinerary is perhaps not as spectacular as the ones above, but it gives a perfect introduction to central Tuscany and includes some of the most scenic towns in the region. You’ll get a taste of the Chianti, see San Gimignano and the area of the ‘balze’ cliffs near Volterra.

scenic drives in tuscany
Volterra – Image by alefolsom from Pixabay

The drive starts in the heart of the Chianti region. From Radda take the SR429 to Castellina in Chianti and savour the landscape of vineyards and verdant woods that characterise this area. Then bear on past the less attractive area of Poggibonsi, and carry on along the SP1 to San Gimignano. This is the epitome of the Tuscan hilltop town, with its Medieval towers still intact. One of the region’s top destinations of all time.

From San Gimignano follow the SP1-SP62 and then head south onto the SP15 to Volterra. This town has a fascinating Etruscan past and amazing views over the surrounding countryside. It’s one of the most charming small towns in Tuscany. The area around Volterra is characterised by the ‘balze‘, steep clay hills that create a unique and otherworldly panorama.

1 day – Radda in Chianti-San Gimignano-Volterra (90 kilometres)

day trip from florence to siena
San Gimignano – Image by Makalu from Pixabay

It’s not hard to find scenic drives in Tuscany, as the region is blessed with gorgeous natural landscape. They have been kept unspoiled thanks to strict regulations that prevent building so that the area maintains the charm Tuscany is famous for. Driving around the countryside, the woodland, and the southern coastal areas is a very rewarding way to explore this enchanting part of the world.

If you’re planning a trip to Tuscany, here are some suggestions for itineraries that you might find useful. Don’t forget to check our 20 favourite things to do in this wonderful region.

And remember, no trip to Tuscany would be complete without visiting some charming small towns and picturesque villages that are off-the-beaten-track.

More ideas for your driving trips?

Check out our driving itinerary to discover the highlights of the Maremma, in southern Tuscany, including the scenic ‘tufa towns’, the Medieval walled village of Capalbio and the Mount Argentario.

Explore a less travelled part of Tuscany with our 2 Day Road trip to the magical land of the Casentino.

Discover the Less Travelled Part of Chianti, central Tuscany, with out itinerary.

Buon viaggio! 🙂