Tuscany is the definition of picturesque. Cobbled streets dotted with flowers. Inspiring views. Quaint streets. Stone houses. And a profusion of terracotta details. Places that are alive with history and romance.

From postcard-perfect Pienza and Montichiello, to mysterious Filetto in northern Tuscany and the ruined San Galgano Abbey there are no shortage of idyllic spots that make for the perfect rural escape. Here we go in search of the most picturesque spots of them all.

Romantic Tuscany

Via dell’Amore, Pienza

Are these the most picturesque places in Tuscany?

MONTEFIORALLE

Perched on a hill above Greve in Chianti, Montefioralle is tiny. So tiny it takes fifteen minute to see it all. But when it comes to appreciating this picturesque corner of Tuscany, it’s another story all together. You could spend hours taking pictures of the arches, stone streets and the hidden corners where vases and flowery windows seem to create quaint little paintings. Here the light seems to caress the stone and the surrounding views only add to the all-round loveliness.  As a bonus, Montefioralle is immersed in vineyards that produce one of Tuscany’s most precious products: the Chianti wine. So, lovely views and a glass of Chianti red, not a bad combination.

picturesque tuscany

Montefioralle

SAN GIMIGNANO

San Gimignano probably doesn’t need any introduction. Arguably the most famous of all Tuscan small towns, it is known for its fourteen tower-houses and its authentic Medieval air. Every corner of San Gimignano looks like it’s posing for a photograph. Some say it’s too touristy. Others swear eternal love to its picturesque squares, the stone well and crenellated towers. All in all – plenty of charm, but with frescoes, art museums, artisan shops, it’s more than just a pretty face.

Top things to do in San Gimignano during your visit.

picturesque tuscany

San Gimignano, Piazza della Cisterna

MONTICCHIELLO

Here’s another master of the picturesque. Monticchiello is a small village near Pienza with a delightful name that sounds too sweet to be true. An ensemble of honey coloured stone edifices gathered around the main square. The displays of flower-filled vases outside the doors and stone staircases are straight out of a fairy tale. From the moment you walk through the ancient gate inside the Medieval walls that embrace the village, you’ll find yourself immersed in visual delights. There’s a little church to visit too, if you can ever stop taking photos.

best places to visit in tuscany in 2018

Monticchiello in the Val d’Orcia

PIENZA

Not far from Monticchiello is the ‘queen’ of Tuscan picturesque small towns, Pienza. For us no visit to the region isn’t complete without a visit here. As Tuscany’s “ideal city”, it’s golden edifices were built according to a master plan by Renaissance architects, employed by Pope Pio II. The idea? To make his hometown visually perfect. Beautiful designed it may be, but the Val d’Orcia landscape that surrounds it and complete the visual spectacle. Unsurprisingly, it’s a UNESCO Heritage Site.

picturesque tuscany

Pienza

An itinerary in Val d’Orcia, the most scenic part of Tuscany.

day trips from siena

Pienza

MONTEMERANO

Heading to the Maremma, in southern Tuscany, we find plenty more small towns that are going to melt your heart. And the village of Montemerano must be at the top of the list. With an ultra-photogenic square and a maze of stone streets, it’s a great place to unwind and immerse yourself in a peacefully quiet atmosphere, where rustic prettiness rules. If you’re in luck, there’ll some colourful laundry hanging from a window or a cat in front of an old door.

Picturesque tuscany

Montemerano, in the Maremma region

SORANO

You could say the Sorano adds a bit of ‘drama’ to the picturesque ideal. Perched – or better said, clinging – to an outcrop of tufa rock, you can’t really tell where the houses begin and the hill stops. With a green chasm beneath it, and a profusion of terracotta roofs and narrow passageways, it doesn’t get more atmospheric than this. Plus, there’s an ancient fortress, a majestic gate, and a bunch of very interesting Medieval buildings.

Sorano is one of the three “tufa towns” of Tuscany, that deserve a visit. For their quaintness as much as for their historic heritage that dates back to the Etruscan.

picturesque tuscany

Sorano

FILETTO LUNIGIANA

Here we travel to the northernmost point of Tuscany, the Lunigiana. If you want to discover another side of Tuscany we advise you to leave the crowds behind and head north. You’ll find a land of castles, thick woods and mountains. Here you’ll find Filetto. Many consider this the prettiest of all the villages in this region. It has conserved its Medieval town plan, with pretty stone arches, towers and defensive walls. Nearby you can visit the Malgrate Castle for filled with atmospheric views and charm.

picturesque tuscany

The hamlet of Filetto, Lunigiana

SAN GALGANO ABBEY

Romantic painters would have loved the ruins of San Galgano Abbey. The romance of this place is beyond question. At least we think so, and that is why San Galgano is our number one picturesque spot in Tuscany.  We absolutely love this ancient Cistercian abbey surrounded by green in the Sienese countryside.

picturesque tuscany

The roof is long gone, and the empty windows frame the blue of the Tuscan sky. You can still imagine the nave, the impressive size of the abbey that was once part of a wealthy and powerful monastery. Today it’s a photographer’s paradise. And many people fly here from all over the world to get married.

san galgano

Getting married in San Galgano