Cypress alleys, patchwork fields and crumbling castellos. Everyone can picture Tuscany, but it’s not always easy to capture the immensity of the endless waves of green you see with the naked eye, or the timeless quality of ancient stone streets. Here are the prettiest places to visit in Tuscany and take pictures according to photographer Mary Quincy.

This little chapel doesn’t have a bad side. Framed between two rows of cypress trees and surrounded by typical Tuscan countryside, it looks particularly wonderful at sunrise and sunset.

San Quirico d’Orcia

If there’s one scenic drive in Italy you need to do it’s the road between Pienza and San Quirico d’Orcia. You’ll want to stop every two seconds along the six miles of magical landscapes. Even if you drive it hundreds of times, you’ll discover new viewpoints along the way – including this one.

Landscapes of Val d’Orcia

The rolling hills of the Val d’Orcia are absolutely what you would expect. After seeing these perfect landscapes in films such as Gladiator or The English Patient, you would think you might be disappointed in real life, but not so.

San Quirico d'Orcia, Podere Belvedere

This view of the Podere Belvedere farmhouse is very much loved by tourists, but be mindful and respectful, because this shot is taken from a field surrounded by private properties. It looks especially magical when the farmhouse is encircled by fog.

View of Ponte Vecchio and city from Piazzale Michelangelo

If you want to capture a complete view of Florence, the Piazzale Michelangelo is the perfect spot to photograph the city and its most famous bridge. Of course it can get quite crowded, so it’s always best to come early in the morning – but be ready to climb a few stairs to get there.

Cathedral of Santa Maria del Fiore

The architecture of Florence is unique, and every detail seems to blend perfectly if you zoom from certain angles. We are used to seeing the Cathedral of Santa Maria del Fiore in its entirety but if you stand far away enough and you own a good zoom lens, you can focus on certain parts of the building, which creates a slightly different photograph.

Cathedral of Santa Maria del Fiore from Piazza di San Giovanni

This cathedral has been photographed many times, and even early in the morning you’ll see people trying to capture it. If you don’t own a wide-angle lens, find an angle that you like and wait until someone strides by: it will show the actual scale of this incredible monument.

View of buildings by the river from Ponte Santa Trinita

When morning light appears and hits the buildings, head to any bridge in Florence to capture the reflection of the different city colours in the river. This shot was taken on the St Trinity Bridge, which is also a great spot for capturing the Ponte Vecchio.

SAN GIMIGNANO

San Gimignano doors

Doors often say a lot about a town. And most of the doors in San Gimignano are worth capturing – taking you back to medieval times. This one makes me wonder how many people have entered and exited through it.

View from San Gimignano bell tower

San Gimignano is known for its 13 sky-high towers, which are as impressive in real life as they are on film. Even if climbing up the tallest of them might not be easy, your efforts will be rewarded by an incredible view of the town from above, and of the surrounding landscapes and valleys.

View from via don Minzoni, San Gimignano

As with most towns, the best viewpoints are outside the centre. Just a 10-minute walk away from the entrance to the town, you’ll find yourself in a more residential area, which gives the best panoramic sights of this beauty on a hill.

Via Palestro at sunset

San Gimignano is a medieval town that transports you back to another time. As soon as you enter the gate, you’ll be in a walled settlement filled with little alleys, stone houses and impressive views of the valley from every corner.

SIENA

View from Torre del Mangia

There are many viewpoints in Siena but this one really stands out. From the Torre del Mangia you can admire the entire city – the rooftops as well as wide-angle cityscape shots.

Santuario di Santa Caterina

The entrance of the Santuario di Santa Caterina is a great spot for a photo because the arches and columns create the perfect frame and invite you in to see more.

Via Santa Caterina

Siena is a hilltop town and you need to be prepared to climb to get where you want to go. But as the city is built this way, it creates different layers when you photograph it and it adds a different sense of perspective. The steep streets will offer many viewpoints and photography opportunities.

Via Diacceto

There is nothing more charming than little Italian shops and trattorias. And Siena has so many pretty façades you’ll want to stop to photograph each one. Add to that a colourful Vespa or a bicycle and you’ve got yourself a very Italian postcard photo.

Piazza San Giovanni

Every detail around Siena Cathedral is a photogenic gem. As it tends to be a crowded place during the day, in order to capture the sides of the cathedral it’s best to get up early. There’s nothing better than to feel like you’re the only one exploring a city.

Duomo di Siena

Piazza del Duomo will surprise you with its architectural details. In complete contrast with the warm colours of most of the houses and buildings in Siena (yellow and orange), the façade of the Duomo di Siena is made of black and white polychrome marble. You can see some colours as well, but the beauty of each detail is definitely eye-opening.

Torre del Mangia from the ground

Whether it’s staircases or modern architecture, you’ll find an original way to capture a city when you look up. If you’re standing in the middle of this square at the bottom of the Tower of Mangia, looking up will create the perfect perspective shot.

View from Torre del Mangia

If you feel adventurous, climb the 400 steps leading to the top of the Tower of Mangia and this 360-degree view will be worth all your efforts. Standing at the top of this symbol of the city, you’ll get to capture rooftops, churches and even people walking on the Piazza del Campo, who will look so tiny you’ll feel like you’re at the top of the city.

View from via Camporegio

One of the best viewpoints from which to catch the sunrise in Siena is via Camporegio. Houses are layered one on top of another, and as soon as the sun comes out you’ll want to sit on one of the benches and marvel at this typical Tuscan landscape.

PIENZA AND SAN QUIRICO

Piazza Martiri della Liberta, Pienza

Every corner of Pienza is a photographer’s dream – from the beautiful streets to the cute exteriors and the amazing views. This shop displayed its products in such a delightful way it was impossible not to capture it.

Corso il Rossellino, Pienza

The streets of Pienza are so charming that you might not even look up and see this brick bell tower right in the centre, but if you’re entering the town on Corso il Rossellino, it will definitely catch your eye.

Via Dante Alighieri, San Quirico d’Orcia

San Quirico d’Orcia is a fortified town from the 11th century and no cars are able to drive in the centre, which makes Via Dante Alighieri (the main street of the town) so agreeable to walk around.

Bottega di Ines, via Dante Alighieri, San Quirico

Bottega means small store, and from the outside this charming shop looks more like a wine bar or restaurant. Well, the Bottega di Ines does both. It sells traditional products and serves big plates of cheese or charcuterie and wine to enjoy on the outside terrace. San Quirico is a little Tuscan town that makes you want to do just that: take a break between all these photo stops and enjoy a peaceful and delicious moment outside.