Imagine standing atop a rustic Tuscan hill, where every direction you gaze offers a stunning panorama that seems straight out of a painting. Tuscany’s hilltop towns provide some of the most breathtaking views in Italy, each offering a unique vantage point over rolling vineyards, ancient olive groves, and charming medieval architecture. For unparalleled vistas, visit San Gimignano, known for its iconic medieval towers that provide a bird’s-eye view of the surrounding countryside.
You’ll also want to explore Volterra, where the views are as rich in history as the town. The elevated position offers sweeping views stretching the horizon, blending the natural landscape with historical richness. Monteriggioni, with its intact medieval walls, serves as a perfect spot for panoramic photos, capturing the quintessential beauty of the Tuscan countryside.
Whether you’re an avid photographer or simply a lover of nature and history, these hilltop towns offer abundant opportunities to capture the essence of Tuscany. As you wander through the cobblestone streets and fortified walls, every corner becomes a new photo opportunity, making your journey an unforgettable visual feast.
Top Hilltop Towns in Tuscany
1. Montepulciano
Montepulciano is a gem in Tuscany, known for its enchanting hilltop location and stunning views. As you stroll through the streets of this medieval town, you’re greeted with breathtaking vistas of the Tuscan countryside.
For some of the best photo opportunities, head to the main square. The panoramic view here, with the historic Renaissance palaces and churches backdrop, is unforgettable.
Another must-visit spot is the Piazza Grande. This elegant square offers a picturesque setting and attracts fans of the “Twilight” movies. The grandeur of the Cathedral of Santa Maria Assunta adds to its charm.
Don’t miss the chance to explore the underground wine cellars. These hidden gems provide a unique experience and impressive views of the rolling hills.
List of top viewpoints:
- Piazza Grande
- Main Square
- Underground Wine Cellars
Bring your camera and capture the essence of Montepulciano, from its historic buildings to the expansive landscapes that stretch beyond the horizon.
2. Montalcino
Nestled on a hill in Tuscany, Montalcino charms with its medieval allure and stunning vistas. The town, known for its fantastic wines, offers a picturesque escape.
One of the best viewpoints in Montalcino is at the old fortress Rocca di Montalcino. From here, you’ll enjoy panoramic views of the Val d’Orcia, which is covered in vineyards and olive groves. This spot is perfect for capturing the beauty of the Tuscan countryside.
The Piazza del Popolo is another gem in Montalcino. The historic square, surrounded by charming cafes and shops, provides a great spot for people-watching and soaking up the local atmosphere. The surrounding buildings offer a beautiful backdrop for your photos.
Don’t miss the chance to explore the narrow, winding streets that lead to unexpected viewpoints. The Torre del Palazzo dei Priori offers an elevated perspective, giving you a bird’ s-eye view of the town’s ancient rooftops framed by lush green hills.
Wine lovers’ experience wouldn’t be complete without visiting the surrounding vineyards. Many provide not only excellent wine tastings but also breathtaking views. Castello Banfi is a notable vineyard offering guided tours where you can photograph the scenic landscapes.
As you wander through Montalcino, every corner reveals a new, enchanting view. Ensure your camera is handy because beauty awaits at every turn in this Tuscan hilltop town.
3. Volterra
In the heart of Tuscany, Volterra is a captivating hilltop town with an Etruscan heritage. This ancient town offers an evocative atmosphere and panoramic views that will leave you in awe.
For breathtaking viewpoints, head to the Rocca di Volterra. From this fortress, you will see sweeping vistas of the surrounding countryside. This is a perfect spot for photos, especially during sunset.
The Piazza dei Priori, one of the oldest squares in Tuscany, offers a stunning look at medieval architecture. Capture the historic Palazzo dei Priori and its neighboring buildings, making it a must-stop for your camera.
Don’t miss the Volterra Duomo. Its facade and ornate interior provide endless photo opportunities. The ceilings of the side chapels and the Baptistery are particularly beautiful.
A short walk to the Parco Archeologico Enrico Fiumi will reward you with incredible views over the town’s rooftops and the valleys beyond. This park combines green spaces with historical ruins, creating a unique picture backdrop.
For a taste of local life, explore the Via dei Sarti. This narrow street, lined with artisan shops and cafes, is ideal for candid shots.
Take in its ancient walls and charming stone buildings as you amble through Volterra’s winding streets. Every corner reveals a new perspective. Its blend of history an
4. San Gimignano
San Gimignano is often called the “Manhattan of the Middle Ages,” thanks to its impressive skyline of medieval towers.
Walking through its narrow streets, you will feel transported back in time. One of the best viewpoints in San Gimignano is from the Torre Grossa.
Climb the 218 steps to the top, and you will be rewarded with a breathtaking panoramic view that stretches over the rolling hills and vineyards below. Make sure to bring your camera to capture this unforgettable scene.
The Piazza della Cisterna offers another excellent photo opportunity. Surrounded by rustic buildings and capped by its iconic well in the center, this square is picturesque and full of history.
The tower-studded skyline provides a stunning backdrop for your photos. As you stroll, don’t miss the chance to explore the Collegiata di San Gimignano. The church offers historical insights and lovely views from its vantage point.
In addition, the town is known for its Vernaccia di San Gimignano, a unique white wine. You can enjoy a glass while soaking in the incredible vistas around you. Each corner of San Gimignano offers another postcard-worthy photo opportunity.
Take your time to meander through its charming lanes and discover hidden gems and scenic spots, ensuring you don’t miss any of the beauty this town has to offer. Whether you are a history enthusiast or simply love stunning landscapes, San Gimignano will leave a lasting impression on your heart.
5. Cortona
Cortona, a charming Medieval hilltop town in Tuscany, offers breathtaking views over the Val di Chiana. Thanks to its picturesque streets and stunning scenic spots, this town has kept its authentic charm despite its rising popularity.
Piazza Garibaldi, also known as Belvedere di Cortona, is one of the must-visit spots. From here, you can enjoy panoramic views that will leave you in awe.
You’ll encounter more beautiful outlooks as you wander through Cortona’s narrow, hilly streets. Each turn provides a new perspective of the surrounding Tuscan landscape, making it a photographer’s dream.
Walk up to Piazza della Repubblica for a blend of architectural beauty and scenic vistas. The historic buildings frame the views perfectly, giving you a sense of returning in time.
Another excellent viewpoint is the fortress of Girifalco. This fortress offers extensive views over the town and the countryside, which is ideal for capturing the essence of Cortona in your photos.
Don’t miss a visit to the Basilica of Santa Margherita, located at one of the highest points in Cortona. The views from here are awe-inspiring, allowing you to see the rolling hills and valleys stretch out endlessly.
Every step in Cortona leads to a new, stunning viewpoint, making it an unforgettable destination for lovers of scenic beauty and history.
6. Pienza
Pienza, a gem of Tuscany, offers views that are nothing short of breathtaking. This medieval hilltop town, recognized as a UNESCO World Heritage site, invites you to wander its charming streets and absorb the picturesque landscapes.
Begin your exploration at the Porta al Ciglio. This spot, near the parking lot, provides stunning vistas of the Val d’Orcia. The rolling hills and expansive fields create perfect photo opportunities, especially during sunrise or sunset.
Stroll along the main street, Corso il Rossellino, lined with quaint shops and galleries. As you walk, each corner offers a new angle of the Tuscan countryside. Don’t miss the panoramic views from the town walls, where the horizon stretches endlessly.
Lastly, visit Palazzo Piccolomini’s garden. Here, manicured lawns frame sensational views of the valley below.
The intimate setting is ideal for capturing the romance of Tuscany and creating lasting memories with your camera. Pienza’s charm and scenic vistas make it a must-visit destination for any traveler.
7. Certaldo
Certaldo Alto, perched on a hill, offers sweeping views of the Val d’Elsa. Take the cable cart from the modern part of town up to Certaldo Alto. It’s an easy and scenic ride.
Boccaccio’s House, located centrally, offers a glimpse into historical architecture and expansive views from its windows.
Stroll through Via Boccaccio. The cobblestone streets and medieval walls provide the perfect backdrop for your photos.
Don’t miss the Town Hall. Its tower offers one of the best viewpoints where you can capture the panoramic beauty of Tuscany.
For a unique viewpoint, check out the Belvedere. This balcony-like spot allows you to view the rolling hills and vineyards that characterize the region.
Charming cafes and restaurants in every corner of Certaldo offer delicious food and stunning vistas. Whether wandering through quiet streets or admiring the landscape, Certaldo has chances to snap stunning photos and soak in breathtaking views.
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Certaldo is easily accessible. Take the FI-PI-LI road from Florence or Pisa, exit at Empoli Ovest, follow signs for Certaldo, or exit Poggibonsi from the Siena direction. Each corner of Certaldo invites you to pause and take in the historical beauty and endless Tuscan horizons.
8. Massa Marittima
Nestled in the Maremma region of southern Tuscany, Massa Marittima is a charming medieval hill town with much to offer.
The Romanesque Cathedral of San Cerbone, located centrally, is a must-see. Its magnificent facade provides great photo opportunities from the piazza.
For sweeping vistas, head to the Torre del Candeliere. Climbing the tower rewards you with breathtaking town and surrounding countryside views.
Wander through the historic streets to soak up the medieval atmosphere and discover quaint shops and cafes. Look out for the Public Fountain, another spot perfect for photos.
Don’t miss visiting the Museo Archeologico to delve into local history. The museum setting provides a scenic backdrop for capturing the town’s essence.
Massa Marittima’s elevated position allows for panoramic views at almost every turn. As you explore, you’ll find multiple viewpoints ideal for capturing the beauty of Tuscany.
9. Anghiari
Anghiari, a picturesque hilltop town in eastern Tuscany, will captivate you with its medieval charm and stunning views. Nestled in the Arezzo province, this stone city sits atop a hill, only 5 km from the Umbria region.
When you visit Anghiari, make sure to explore the historical center. The narrow, winding streets and ancient stone buildings provide countless photo opportunities. The town’s location offers panoramic views of the Tiber Valley below, making it an ideal spot for landscape photography.
One of the best viewpoints in Anghiari is from the Church of Santa Maria delle Grazie. The lookout spot provides sweeping vistas of the surrounding countryside, especially during sunset. The blend of colors is mesmerizing.
Another must-see is the Piazza Baldaccio, where you can soak in the medieval atmosphere and capture the town’s essence. The piazza offers a fantastic backdrop of historical architecture that will make your photos stand out.
Don’t miss the Craftshops of Anghiari. These quaint shops add character to the town and offer unique items perfect for capturing the local craftsmanship. It’s a great place to take close-up local arts and crafts shots.
Lastly, consider a short walk to the ancient walls and gates of the town. These formidable structures offer historical insight and picturesque perspectives of Anghiari’s landscape. Your visit will be richly rewarding and visually stunning.
10. Radicofani
Radicofani is a charming hilltop village in Val d’Orcia, Southern Tuscany. Perched high on a volcanic cliff, this medieval town offers some of the most stunning panoramic views imaginable.
Best Viewpoints
- The Fortress of Radicofani: Built in the 10th century, this imposing structure provides a vantage point over the entire Val d’Orcia. Make sure to visit the tower for 360-degree views.
- The village center: Take a stroll through the narrow streets. The views from the piazza are spectacular, especially at sunset.
- Surrounding hills: Explore the trails around the village for unique photo opportunities. The rolling hills and cypress trees create perfect Tuscan scenery.
Photo Opportunities
- The Fortress at Sunrise: Capture the early morning light as it illuminates the ancient stone walls.
- Via Francigena: Discover this historic pilgrimage route cutting through the town. It makes for an excellent backdrop for photos.
- Panoramic Vistas: The sweeping valleys and distant mountains make incredible photos everywhere you turn.
Radicofani isn’t just about the views. While you’re here, immerse yourself in the local culture. Stop by small cafes and enjoy some Tuscan cuisine. Each corner of this village holds a history waiting to be explored and photographed.
