You’ve decided on Tuscany. You’ve booked your flights. Now comes the hardest part: where exactly should you stay?
For many of our guests, the final decision comes down to a battle between the two most famous regions: the wine-rich hills of Chianti in the north, and the golden, rolling landscapes of the Val d'Orcia in the south.
Both are undeniably beautiful. Both offer incredible food. But the experience of renting a villa in each is completely different.
To help you choose the perfect base for your holiday, we’ve broken down the differences in landscape, logistics, and "vibe."
At a Glance: The Quick Comparison
| Feature | Chianti | Val d'Orcia |
|---|---|---|
| Best For... | First-timers, wine lovers, & those wanting easy access to Florence. | Photographers, honeymooners, & "Slow Travel" seekers. |
| The Landscape | Green, wooded, steeper hills, endless vineyards, and castles. | Open, golden wheat fields, clay hills (Crete Senesi), and cypress avenues. |
| Drive to Florence | Short (30–50 mins). | Long (1 hr 45 mins – 2 hrs). |
| Vibe | Busy, sophisticated, "market town" energy. | Quiet, ethereal, romantic, distinctively rural. |
| Key Towns | Greve, Radda, Castellina, Gaiole. | Pienza, Montalcino, Montepulciano. |
Chianti: The Heart of the Action
Chianti (specifically Chianti Classico) is the area stretching between Florence and Siena. It is arguably the most famous wine region in the world.
Why choose a villa in Chianti?
- Location, Location, Location: If you want to visit Florence multiple times for dinner or museums, Chianti is your best bet. You can easily drive to the outskirts of the city in 40 minutes, or catch a bus from towns like Greve.
- The "Green" Landscape: Chianti is lush. The hills are steeper and often covered in thick oak forests (great for shading your villa pool!) broken up by geometric rows of vineyards.
- Active Energy: Because it is closer to the cities, the towns here—like Radda and Greve—bustle with life year-round. You are never far from a world-class restaurant, a wine tasting tour, or a busy Saturday market.
The Trade-off: It is more populous. In high season (July/August), the roads can be busier, and you are less likely to find "total isolation" compared to the south.
Our Advice: Choose Chianti if this is your first trip to Tuscany and you want to "do it all"—museums, cities, and wine.
Val d'Orcia: The Postcard Dream
Drive about an hour south of Siena, and the world changes. The forests disappear, replaced by vast, open rolling hills that turn emerald green in spring and golden yellow in summer. This is the Val d'Orcia (a UNESCO World Heritage site).
Why choose a villa in Val d'Orcia?
- The Views: This is the Tuscany you see on postcards. The famous "winding road lined with cypress trees" is here. If you are a photographer or just want to sit by the pool staring at a view that stretches for 30 miles, this is it.
- Renowned Hill Towns: The towns here—Pienza, Montalcino, Montepulciano—are architectural jewels perched high on hilltops. They feel more medieval and slightly slower-paced than their northern cousins.
- Thermal Spas: This area is rich in natural hot springs. Towns like Bagno Vignoni offer incredible thermal waters perfect for relaxing after a day of sightseeing.
The Trade-off: It is remote. A day trip to Florence is a long haul (2 hours each way). You need to be comfortable driving, as amenities are more spread out.
Our Advice: Choose Val d'Orcia if you’ve been to Tuscany before, or if you want a purely relaxing, romantic escape where the goal is to slow down, drink Brunello wine, and watch the sunset.
The Verdict
Still undecided? Think of it this way:
- Rent in Chianti if: You want to wake up, have a quick swim, drive into Florence for lunch, and be back at your villa for a wine tasting by 5:00 PM.
- Rent in Val d'Orcia if: You want to wake up, spend 2 hours lingering over coffee watching the mist clear off the hills, visit a local cheese farm, and not see a traffic light for a week.
Need help deciding? Our team visits every villa personally. We know which house has the best sunset view in Pienza and which has the quickest shortcut into Florence.
Contact us for a personal recommendation or Search all Villas in Tuscany
Author: Dan Wrightson
Dan Wrightson grew up in Tuscany, Italy and has been writing about, sketching and exploring Tuscany and Italy since 1983.
1st Jan 2026 30th Nov 2025