Three Scenic Drives in Tuscany I Never Rush
A guide to some of the most beautiful scenic drives in Tuscany — from Chianti to the Val d’Orcia.*
Some of my favourite moments in Tuscany have happened on the road.
After more than twenty years of driving the highways, back roads, and tiny vineyard lanes of this region, I’ve learned that some of the most memorable experiences aren’t always in the towns themselves — they’re in the countryside between them.
If you enjoy a Tuscany road trip, these drives are among the ones I return to again and again. They’re perfect when you’re staying at a villa in Tuscany and want to explore slowly, stopping whenever the landscape invites you to.
Here are three of my favourites.
1. The Chiantigiana Road (SR222) - Florence to Siena
The SR222 — known as the Chiantigiana — is one of the most classic drives in Tuscany.
This road winds through the heart of the Chianti Classico wine region between Florence and Siena. Vineyards roll across the hillsides, cypress trees line the ridges, and small stone villages appear along the way.
It’s not a drive to rush.
Stop for coffee in Greve, wander through Panzano, or pause in Radda in Chianti for a glass of wine and a view over the hills.
Map link:
This is one of those scenic drives in Tuscany where the journey itself becomes the experience.
If you’re looking at private villas in Chianti this is one of the reasons I always say location matters so much.
2. Monticchiello to Pienza/ Val d’Orcia
The road between Monticchiello and Pienza may be one of the most photographed drives in all of Tuscany.
The Val d’Orcia landscape unfolds here in soft, sweeping hills, winding roads, and iconic viewpoints that feel almost cinematic.
Along the way you’ll pass the famous Cappella della Madonna di Vitaleta, a tiny chapel framed by cypress trees that has become one of the most recognizable scenes in the Tuscan countryside.
Many travellers stop here for photographs — and for good reason.
Map links:
Cappella della Madonna di Vitaleta
This short drive is a perfect example of why driving in Tuscany can be such a joy.
For anyone considering villas in the Val d’Orcia ( one example) this is one of the loveliest areas to base yourself.
The Crete Senesi Roads near Asciano
Just southeast of Siena lies a very different landscape known as the Crete Senesi.
Instead of vineyards, you’ll find rolling clay hills that change colour with the light and the seasons. The scenery here feels almost abstract — long horizons, winding roads, and solitary farmhouses sitting on distant ridges.
For photographers, this area is extraordinary.
For drivers, it’s simply peaceful.
Starting from the small town of Asciano, you can wander through the countryside with no particular destination — which is often the best way to experience this part of Tuscany.
A worthwhile stop along the way is the Abbazia di Monte Oliveto Maggiore, a striking Benedictine monastery set among the clay hills. The approach alone is beautiful, and the quiet cloisters and frescoed corridors make it a fascinating place to explore.
Map links:
Abbazia di Monte Oliveto Maggiore
Why Driving Is One of the Best Ways to Experience Tuscany
Many visitors focus on Tuscany’s famous villages — and they are wonderful.
But some of the most beautiful moments happen while driving through Tuscany’s countryside, moving slowly from one hill town to another.
When my clients stay in a villa in Tuscany, I always encourage them to allow time for these kinds of drives.
Stop for a photograph.
Pull over for a view.
Follow a road simply because it looks interesting.
Often those are the moments people remember most.
Scenic Drives in Tuscany – A Few Practical Tips
If you’re planning a Tuscany road trip, a little preparation makes the experience even more enjoyable.
Many of the most beautiful scenic roads in Tuscany are narrow country lanes winding through vineyards and farmland. Drive slowly and allow time for spontaneous stops — some of the best views appear unexpectedly around a bend in the road.
Morning and late afternoon are also the best times for exploring. The light is softer, the roads are quieter, and the Tuscan countryside reveals its colours beautifully.
These are the kinds of small details that make driving in Tuscany such a memorable part of a trip.
Planning a Villa Stay in Tuscany?
One of the great pleasures of a Tuscany road trip is discovering the countryside at your own pace.
Choosing the right base makes all the difference. With the right villa location, many of the most beautiful scenic drives in Tuscany — including Chianti, Val d’Orcia, and the Crete Senesi — are easy half-day outings.
If you're considering a villa in Chianti or the Val d’Orcia and aren’t sure which area would suit you best, feel free to get in touch. After more than twenty years exploring and driving in Tuscany, I’m always happy to share what I’ve learned.
You’ll also find more Tuscany travel notes, village guides, and villa ideas on ClassicVacationRental.com
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