Experience Tuscany: Bask in Stunning Scenery

One of Tuscany’s calling cards is its scenery:  Sumptuous, extravagantly green, undulating farm fields that look like a painting. Hillsides grooved with twisty rural roads, lined with pointy cypress trees. Stately churches, humble chapels, rustic farmhouses, and circles of trees perched just so in resplendent tableaus.

There are a handful of places I’ve been that I describe as “mind-bending” — places with a unique, otherworldly quality: Norway’s Lofoten Islands. Australia’s Uluru. Slovenia’s Julian Alps. The Oregon Coast. And, of course, the Heart of Tuscany.

“Heart of Tuscany” is my nickname for the corridor connecting the hill towns of Montepulciano, Pienza, and Montalcino, plus a few little side-trips within about a 30-minute drive of that spine. Italians know this area as the Val d’Orcia.

It’s not just the landscape. Beauty is in the DNA of Tuscans. One Siena native recently told me that Tuscans consider themselves the inheritors and stewards of a centuries-long legacy of beauty. Every tree that’s planted, every farmhouse that’s restored, every road that’s re-routed — it’s all carefully considered not only on practical or economic merits, but also on aesthetics. If Tuscans sometimes come on a little strong preaching the glories of their land…well, that’s why.

A few years back, drunk on all this wondrous scenery, I decided to scour the Val d’Orcia to compile a “greatest hits” list of calendar-worthy Tuscan tableaus. I got suggestions from several Tuscan friends, who nominated their picks. And I came up with this rundown for our Rick Steves Florence & Tuscany guidebook (where you’ll find all the details):

Cypress-Lined Driveways

You’ll find dozens upon dozens of these in your Tuscan travels. But two classics are the perfectly twisty road near La Foce gardens (pictured above), and the one cresting a hill adjacent to Monticchiello.

Circle of Cypresses (Rondò)

This ring of cypress trees stands dramatically alone on a gently sloping hillside of brilliant-green-in-springtime crops, alongside a highway just west of San Quirico d’Orcia. Planted as a shelter for shepherds caught out in the elements, today it’s one of Tuscany’s top photo ops.

Chapel with Trees

The super-scenic road between San Quirico d’Orcia and Pienza (SP-146) has several fine viewpoints, but the best-known is the tidy little Cappella della Madonna di Vitaleta on a ridge, flanked by pudgy cypress trees.

Farmhouse with Trees

On the same road, just outside of Pienza, is a classic “farmhouse with trees” scene.

Farmhouse with Twisty Driveway

From anywhere along Pienza’s panoramic terrace, just gaze off to the south. In the foreground, you’ll see a perfect little farmhouse with a meandering driveway (made famous as the home of Russell Crowe in Gladiator).

Honorable Mention

The list goes on and on. Just to round out our scenic little loop through the Val d’Orcia, here’s a little more “honorable mention” eye candy:

The view down from Montepulciano’s summit, with the Church of San Biagio

A driveway off of road SP-146, near Cappella della Madonna di Vitaleta

Sant’Antimo Abbey, outside of Montalcino

Tuscan Street Scenes

And, if you’ve never thought of town streets as “scenery,” Tuscany might just change your mind:


Back-streets Pisa

Lucca again


Lucca yet again

What’s your favorite Tuscan tableau?

Heading to Tuscany? I share a dozen of my favorite Tuscan experiences here.

Our new Best of Tuscany in 12 Days Tour — which begins in 2020 — incorporates many vivid experiences in Italy’s heartland…including drives through sumptuous scenery like what I’ve described here.

Or, to do it on your own, you’ll find all of the details you need in our Rick Steves Florence & Tuscany guidebook.

4 Replies to “Experience Tuscany: Bask in Stunning Scenery”

  1. We stayed in Gaiole in Chianti and enjoyed every view from our B&B. The best views, though, were from the back of one of the shops in Monticiano. After a heavy storm, the owner invited us to enjoy the view of the valley from a balcony in the back of his store. It was breathtaking.

    1. Susan, I had a similar experience in Montalcino earlier this summer! Many of those nondescript shops along the main drag look out over stunning Tuscan vistas. What a memory!

  2. This article comes to me at a most perfect time! My daughter will be studying this fall in Sansepolcro and my husband and I will be visiting…of course! This is likely a silly question, but I’ll ask anyway…I’m assuming that having a car to travel throughout some of Tuscany is the best way to do so? Thank you for all you do to fuel my wanderlust!

    1. Hi Lisa! Yes, I love having a car in Tuscany–particularly for all that glorious countryside. The only caution is to keep a very careful eye out for “ZTL” zones. This stands for “zona trafico limitato”–areas (usually in historic town centers) where traffic is limited to locals only. These are always marked by a “ZTL” sign and a red circle. If you get careless and drive past one of these signs, you could be on the receiving end of a big ticket. (In bigger cities, this can be controlled by cameras, so a ticket is a sure thing.) As long as you are careful to avoid ZTL zones–park outside of those areas and walk in–a car is wonderful here. (One more tip: Some hotels have permission to let their guests park inside ZTL zones, and others can tell you the best place to park to avoid ZTL zones, so I always ask my hotel ahead of time what they recommend.) Happy travels!

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