Tuscany Photo Spots

With rolling hills, lines of cypress trees, stunning villas, and vibrant sunsets — Tuscany is one of the most picturesque places in all of Italy. Located three hours north of Rome, there is so much to explore in this abundant region. And that includes food! Rich olive oil, delicious wines, gourmet cheeses, fragrant truffles — these are just a few of the amazing Italian treats you’ll enjoy in the Tuscan countryside. Between the delicious cuisine, the gorgeous landscapes, and the medieval architecture, Tuscany is a sensory delight. Naturally, that means there are countless photo opportunities to take advantage of. Read on to discover the best places to take photos in Tuscany. 📸

Photo: Emma in Tuscany for Flytographer. Andres and partner capture memories on a custom route in Tuscany with an engagement photoshoot with Flytographer.

1. Chianti Region

The Chianti region is one of the most beautiful and well-known areas in Tuscany. Chianti offers a unique landscape; it’s an especially mountainous area with rolling green hills covered in rows of vineyards and olive tree groves. The stunning landscape is dotted with stone villas and countryside homes. These picturesque scenes stretch as far as the eye can see, as the region sprawls between Florence and Siena — nearly 100 kilometers! 

And let’s not forget the wine. 🍷Known for its distinctive red blend of Sangiovese grapes, Chianti wine is as essential to Italian cuisine as olive oil, fresh tomatoes, and balsamic vinegar. If you’re looking for a classic Tuscan wine tasting experience, Chianti is a fabulous region to explore.

Photo: Emma in Tuscany for Flytographer. Karen and family capture memories of their trip at Villa l’ Olmo del Chianti in Tuscany on a family photoshoot with Flytographer.

2. Pienza

Located in the Val d’Orcia, Pienza is a charming and tiny village well worth a visit. Known as the ‘ideal city of the Renaissance,’ Pienza was built with the idea of a utopian city in mind.

As you wander through the village, this inspiration is evident! Everything from the town’s position atop a hill to the construction of charming stone buildings captures the ideals of classical times. 

To explore all Pienza has to offer, start with a stroll around the borders of the town to take in the panoramic views of Val d’Orcia. From there, wander through the narrow streets to enjoy the stone architecture and local shops, including locally made pecorino cheese — the city’s specialty! 🧀 Make your way to the historic city centre where the iconic Il Duomo di Pienza stands.

Just 15 minutes away, you’ll find the quaint town of San Quirico d’Orcia. On your journey from Pienza to San Quirico d’Orcia, you’ll come across breathtaking scenes that are perfect photography locations. About halfway, you’ll spot a cluster of cypress trees on otherwise sparse rolling hills — these are the most photographed trees in all of Tuscany! 🌲

The area is also home to the Chapel of the Madonna di Vitaleta, a UNESCO World Heritage site dedicated to the Virgin Mary. The tiny, secluded chapel is bordered by rows of cypress trees, making for a unique photo opportunity. 📸

Photo: Emma in Tuscany for Flytographer. David and family capture memories of their trip at Pienza in Tuscany on a family photoshoot with Flytographer.

3. Siena

Known as the prettiest and best-preserved medieval town in Tuscany, Siena is a must-see! At the heart of the city, you’ll find the central square, Piazza del Campo. Known for the Palio — a horse race that occurs every summer — many travellers visit this location for the event. 🏇But, with its grand open square surrounded by classic medieval architecture, it is worth a visit any time of year! 

The city has many hilly, narrow streets that open up to inviting squares and majestic cathedrals, including Basilica di San Domenico. You’ll also enjoy views of the city’s many landmarks from the top of the hills.

For a unique Tuscan experience, consider visiting a farmhouse that offers agriturismo — the practice of welcoming guests for food and relaxation. 🍝 There are fabulous accommodation options — like Poggio Covili or Baccoleno — that specifically offer this experience. Indulging in locally-crafted Italian foods while taking in the Tuscan landscape? It doesn’t get better than that!

Photo: Emma in Tuscany for Flytographer. Wendy and family captures memories of their trip at Siena in Tuscany on a family photoshoot with Flytographer.

4. Florence

Located right in the heart of Tuscany, Florence will captivate you the moment you arrive. 💖Florence is a hub of cultural significance. Home to renowned landmarks including the Cathedral of Santa Maria del Fiore — also known as the Duomo, historical sites like Ponte Vecchio, and the world-class Uffizi Gallery, there is so much to explore in this fabulous city.

As the city is quite walkable, it is best explored on foot! Consider taking a walking tour to learn the rich history of the city and the best spots for a bite. Wander through the leather market for fine Florentine goods then pop by the modern Mercado Centrale for a lunch experience you won’t soon forget.

Start at the Piazza del Duomo for a lovely afternoon walk with plentiful photo opportunities. The cathedral is a show-stopping masterpiece with intricate and colourful patterns adorning the entire facade. 😍This, paired with its impressive size, makes for an instantly recognizable landmark — and an absolutely gorgeous backdrop for photos.

From there, head to the Arno River for a view of Ponte Vecchio, a medieval bridge lined with shops on either side. Take some time to stroll around the medieval backstreets for boutique shopping. Be sure to indulge in gelato while you’re at it! 🍨

Continue toward Piazzale Michelangelo, where you’ll find a replica of Michelangelo’s David as well as a panoramic view of Florence’s skyline. This is a fabulous place to watch the sunset — and a picture-perfect place to capture your Florence memories. 🌅

💡Travel tip: Well-connected by train, Florence is a great home base for day trips to cities like Arezzo, Pisa, and Siena, so consider staying here and venturing out as you please.

Photo: Ellie in Tuscany for Flytographer. Tamara and partner capture memories of their honeymoon at Duomo & Ponte Vecchio on a couples photoshoot with Flytographer.

5. Arezzo

For those looking to follow the path less-travelled, Arezzo is the place! The city offers all the usual Tuscan charm with fewer crowds. Located just an hour train ride from Florence, Arezzo is an ideal destination for a day trip. 

Known for its art and shopping scenes, there is so much to explore in this town. The narrow streets are lined with fabulous clothing and jewellery boutiques, antique shops, and lively eateries with fresh products from the nearby Valdichiana and Casentino Valleys. 

As you wander through the streets, you’ll see a mix of both medieval and gothic architecture. Visit the picturesque Piazza Grande for a great view of varying architectural types. Perhaps the best photo spot in all of Arezzo! 📸

Photo: Emma in Tuscany for Flytographer. Amie and family capture memories of their trip at The Villa in Arezzo, Tuscany on a family photoshoot with Flytographer.

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6. Palazzo Pretorio

Located in the city of Prato, the Palazzo Pretorio is a historic building that is now home to the Civic Museum of Prato. Once operating as a city hall in medieval times, it now houses elaborate frescos and other classical art pieces. 🖼️

Situated on the corner of Piazza del Comune, its height and architecture immediately catch your eye. With the vast open space of the square and a stunning water fountain out front, this is a seriously Instagrammable locationand one of the best places to take photos in Tuscany!

Photo: Emma in Tuscany for Flytographer. Beaven and family capture memories of their trip at a custom route in Tuscany on a family photoshoot with Flytographer.

7. Cortona

The quaint town of Cortona offers a little bit of everything — jaw-dropping views of the Tuscan countryside, a rich history, and a delicious food scene. Dating back to Etruscan times, the village houses many interesting places to visit, including the Etruscan Academy Museum which showcases various archaeological artifacts.

The city is enclosed by stone walls and sits on the top of a hill about 600 meters, or 1968 feet, high. This position over the valley offers a clear view of the surrounding valley all the way to glittering Lake Trasimeno. Wander along the path that follows the city walls to enjoy a lovely view of the surrounding countryside.

Stroll through the main streets of the village to discover locally handmade items and boutique shops. Enjoy traditional Tuscan cuisine at one of many lively eateries throughout the town — fabulous wines are made in the area, so be sure to indulge in a glass if you enjoy vino! 🍇

Photo: Emma in Tuscany for Flytographer. Celesta and family capture memories of their trip at San Gimignano in Tuscany on a family photoshoot with Flytographer.

8. San Gimignano

San Gimignano is a walled town located between Florence and Siena. As a UNESCO World Heritage Site, this hilltop town has well-preserved medieval architecture, including its famous five towers, and impressive views of the surrounding Tuscan countryside. These traits make it a beautiful place to take photos in Tuscany. 🏰

Visitors can stroll through the narrow cobblestone streets lined with shops and restaurants. There are fabulous wine shops in the village which offer tastings of locally-made products, including truffle honey and the region’s very own white wine, the Vernaccia di San Gimignano.

Photo: Emma in Tuscany for Flytographer. Celesta and family capture memories of their trip at San Gimignano in Tuscany on a family photoshoot with Flytographer.

9. Montepulciano

Located in southern Tuscany, Montepulciano is a medieval town home to Renaissance palaces, ancient churches, and charming squares. The lovely village also boasts panoramic views of Val d’Orcia and Val di Chiana, two of Tuscany’s prettiest valleys.

A leisurely walk through Montepulciano is the best way to explore the landmarks and stunning views of the surrounding Tuscan countryside. Start your journey at Piazza Grande. Grab a cappuccino at one of the cafes and enjoy the scenic architecture surrounding the square. ☕ From there, take your time to explore the family-owned shops surrounding the square. Wander toward Il Corso, Montepulciano’s picturesque main street, home to more fabulous shops and eateries.

Photo: Emma in Tuscany for Flytographer. Margo and partner celebrate their anniversary at Montepulciano in Tuscany with a couples photoshoot with Flytographer.

10. Capannelle

Capannelle is an iconic winery located in the Chianti region of Tuscany. When you think of a Tuscan winery, elegant stone villas and lush green acreages likely come to mind. And Capannelle fits this description making it one of the best places to take photos in Tuscany! 

Housed in a classic Italian villa, the winery offers a fabulous wine-tasting experience. The exquisite tasting room house a 16th-century long table where visitors can enjoy a selection of food and wine pairings. 🍾

The estate itself sprawls over nearly 90 acres of land, mostly covered with Sangiovese vineyards. But the most striking area is the gardens surrounding the building — lush greenery, ornate fountains, vibrant flowers, and eye-catching pergolas all come together in one swoon-worthy scene. A magical moment to capture! 💫

Photo: Sonya in Tuscany for Flytographer. Katie and partner celebrate their anniversary at Capannelle in Tuscany on a couples photoshoot with Flytographer.

Capturing memories in Tuscany

Rich in history, gourmet foods, and natural beauty, Tuscany is a dreamy destination and truly one-of-a-kind. From rustic farmhouses to medieval towns to sprawling vineyards, the Tuscan countryside is full of beautiful places. Connect with a local photographer to capture your memories on your trip to Tuscany. ✨