The timeless landscapes of Tuscany need no introduction and only four wheels (or two, if you’ve overdone the cheese, pasta and wine) to appreciate fully. Between Florence and Sienna, iconic postcards come to life in Val d’Orcia, a particularly stunning area with cypress-dotted hills and fortified villages producing some of the country’s greatest wines. Here’s an itinerary you can do in a day from Florence, though you’re likely going to want to stretch that over at least two or better three days to fit in more stops.
Pienza – the pearl of the Renaissance
Built from the ground up as a model Renaissance town in the 15th century, Pienza is a feast for the eyes. Enter via Porta al Murello into what was once considered the “ideal city” for a rewarding stroll.
Medieval alleys lead to hilltop views and a whole lot of house envy. The best thing is, this town is so small, you can explore every nooks and crannies without fear of getting lost. The center is always roughly a 3-minute walk away.
Take Via Gozzante which hugs the southern side of the hilltop town.
It’s a never-ending panoramic vista over the lush countryside.
What was once the city patrol path is now one of the most scenic and romantic belvedere.
Splendid architecture
The panoramic walk will bring you right between the cathedral and the palace, the two most famous buildings in Pienza.
Standing on Piazza Pio II, the heart of the city, in front of the white Cattedrale dell’Assunta deserves a pause. Admire the classical lines, marble columns, imposing palazzo next door… and realize this was all built within three years.
Combined with the enchanting urban layout and the soft, creamy glow of the travertine façades – it’s no surprise this entire town was declared a UNESCO World Heritage Site.
Say cheese
Do not leave Pienza without tasting what the town is most proud of – its barrel-aged pecorino.
Made from sheep’s milk and matured for at least 90 days in oak barrels often passed down from nearby wineries, Pienza’s famed pecorino is not to be confused with its namesakes from Rome or Sardinia. This is an intense, flavorful hard sheep cheese that comes in a dizzying array of flavors. Tasting various interpretations should be part of every visit to the city.
Make sure you’ve taken every possible turn and many snapshots of this impossibly photogenic town before getting back into your car – you’ll want to remember this tiny utopian village with as much details as possible.
Movie set
In between medieval hamlets, scene-stealing landscapes unfold all around with some that may appear very familiar. The iconic gently rolling hills of Val d’Orcia have been featured in many movies. One particular chapel, the Capella di Vitaleta, is one of the most recognizable sights and a favorite stop of photographers. You might recognize it from Ridley Scott’s Gladiator (2000).
You can also stop nearby to see another famous background of the movie, the home in Maximus’s visions which is a private farmhouse.
The Cypress Circle (San Quirico d’Orcia) is a small cluster of trees arranged in a ring and might just be the most iconic cypress trees location in Tuscany. You can park by the road and walk up to them for your photoshoot.
More photos of cypress trees await on the road up to the farm stay Poggio Covili.
Standing in the middle of this long avenue lined with tall cypress trees is simply striking.
Unsurprisingly, golden hour is the best time to be here (and sunrise might be a close second). The light changes constantly and the entire landscape takes on a soft, golden glow as if freshly painted by the best impressionist.
Baccoleno – THE postcard moment
Save the best for last and time your visit to the most famous viewpoint in all of Tuscany for sunset – Agriturismo Baccoleno.
It simply cannot get more Tuscan classic than the S-curve road lined with cypress trees leading to an estate.
Many people come here at sunset to witness one of the most photogenic places on earth. Even if you’ve seen the photo many times as is surely the case, the light and the wild grasses dancing with the wind bring that extra dose of enchantment to an already superlative panorama. Snap a few photos for your desktop wallpaper and sit down to enjoy the sun dipping straight in front of you – what a breathtaking spectacle.
That’s all we’ve covered in a short day but there is plenty more if you have time, especially if you’re into wine. Nearby you’ll find Montepulciano and Montalcino who produces some of Tuscany’s most prized wines, including Brunello di Montalcino and Vino Nobile di Montepulciano.
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