Medieval tower houses in the Historic Centre of San Gimignano, UNESCO World Heritage Site, San Gimignano, Tuscany

Florence's Postcard-Perfect Villages: 10 Scenic Spots to Explore

What are the Prettiest Towns near Florence?

With their rolling hills, rich artistic heritage, and scenic landscapes, the most beautiful towns near Florence are simply gorgeous. Exploring these pretty towns offers a blend of history, architecture, and authentic Tuscan charm, ideal for curious travelers and those seeking hidden gems beyond the city.

From medieval hilltop villages to enchanting countryside escapes, you’ll find a mix of cultural wonders, local flavors, and striking photo opportunities. Whether you’re looking for sweeping views, vibrant markets, or peaceful strolls, these destinations invite you to slow down, savor authentic Italian life, and create lasting memories just a short trip from Florence.

1. Marradi

A pretty town famous for local chestnuts

Marradi Renaissance architecture of Basilica di San Lorenzo against clear sky on sunny day, Florence, Italy.

Good for: Photo, History


If you love nature and history, Marradi is a superb choice. Located along the River Lamone and surrounded by wooded mountains, Marradi offers a relaxed pace and plenty of opportunities for hiking. The town’s highlights include the elegant Teatro degli Animosi and the Renaissance-style town hall, with the ancient Badia di Santa Reparata monastery just outside town.

While exploring, try the local Marron Buono chestnuts, especially during the lively October festival. Take a stroll to the Romanesque Church of San Lorenzo or enjoy a ride on the steam train that arrives during festival season. For a peaceful break, pick one of the well-marked hiking trails.

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Marradi

2. San Godenzo

An amazing combo of nature and art

San Godenzo Exterior view of the facade of abbey of San Gaudenzio in San Godenzo. Built in the 11th century in Romanesque style, is one of the milestone of the Dante's Way.

Good for: Photo, History


San Godenzo is a quiet village with a rich history, nestled at the foot of Mount Falterona. The Benedictine abbey from the 11th century is a must-see, featuring stunning Romanesque architecture and beautiful artworks. Art lovers will appreciate the wooden statue of Saint Sebastian and the crypt containing the urn of San Godenzo.

Outdoor enthusiasts can explore the green valley and nearby Castagno d’Andrea, birthplace of Renaissance painter Andrea del Castagno. For a unique experience, hike the scenic trails around the municipal territory and enjoy the tranquil surroundings. Don’t leave without trying the delicious local honey.

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San Godenzo

3. Barberino Val d’Elsa

Where rustic Tuscan flavors shine

Barberino Val d’Elsa Appiano, Florence.

Good for: Photo, History, Food


Barberino Val d’Elsa is a fortified village known for its Etruscan roots and medieval charm. Situated almost halfway between Florence and Siena, it’s ideal for both history buffs and foodies. With medieval walls, ancient burial grounds, and Renaissance touches, you get a real sense of Tuscany’s past as you wander through the village.

Stop by local restaurants for classic Tuscan fare like handmade pasta and wild boar stew. Explore artisan shops tucked under porticoes and don’t miss the panoramic views from the village walls. Take a guided walking tour to learn about the area’s Etruscan history.

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Barberino Val d’Elsa

4. Anghiari

Steep streets teeming with tales of epic battles

Anghiari, in the Province of Arezzo, Tuscany, Italy.

Good for: Photo, History, Couples


Anghiari, located in the province of Arezzo, is famous for its dramatic medieval streets and its historic battle. Stroll through the town’s winding lanes and discover charming stone houses and small piazzas that evoke centuries of history.

Climb up to one of the panoramic viewpoints for breathtaking views over the valley. Sample local specialties at family-run trattorias or visit the Anghiari Museum to learn more about the legendary battle. Take one of their fascinating guided tours that really bring the town’s history to life.

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Anghiari

5. San Gimignano

Home to a towering skyline and sweeping countryside views

Tuscan medieval town old street in San Gimignano, Tuscany, Italy.

Good for: Photo, History


San Gimignano is a striking hilltop town southwest of Florence, instantly recognizable by its medieval towers. This well-preserved village is often called the “Medieval Manhattan” and offers sweeping views of the Tuscan countryside. History buffs and photographers will love exploring the stone streets and vibrant piazzas.

Visit the town’s gelaterias for award-winning ice cream and browse shops selling saffron and local wine. Climb the Torre Grossa for panoramic photos or relax in the main square with a glass of Vernaccia. For a smooth trip, take the bus from Florence, but check schedules ahead because transfers are required in Poggibonsi.

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San Gimignano

6. Greve in Chianti

A day trip into Chianti wine country

Medieval Montefioralle in the Florentine Chianti region in the municipality of Greve in Chianti.

Good for: Photo, Couples, Food


Greve in Chianti is often called the gateway to the Chianti region, making it a top pick for wine lovers and foodies. The town’s triangular Piazza Matteotti is surrounded by porticoes filled with artisan shops and cafes. Greve is also a great base for exploring vineyards and local olive groves. If you’re traveling by bus, Greve is easily reached from Florence in about an hour.

Sample Pecorino cheese or taste the famous Chianti Classico at wine bars around the square. Visit the Saturday market to pick up fresh produce and handmade goods for a top-tier picnic.

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Greve in Chianti

7. Montaione

Famed member of the National Truffle City Association

Tuscany, Montaione, the chapels of San Vivaldo, also known as Little Jerusalem, contain sculptures depicting the life of Jesus, from the Della Robbia school.

Good for: Photo, History, Unusual


Montaione offers stunning landscapes and a charming historic center perched high above river valleys. This tranquil village is famous for its natural springs and the San Vivaldo complex, where chapels and churches recreate Jerusalem’s holy sites. Travelers seeking peaceful scenery and cultural exploration flock to its storied streets.

Enjoy local specialties like truffle dishes and regional wine in cozy cafes before taking a guided tour of San Vivaldo’s chapels. if you visit in spring, hike the nearby trails and marvel at the wildflowers in the surrounding countryside. Alternatively, come in October for the famed Tartufesta and learn about all things truffle.

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Montaione

8. Passignano

For lakefront sunsets accompanied by live music

View of Passignano sul Trasimeno, Lake Trasimeno, Perugia, Umbria, Italy.

Good for: Photo, History


Passignano sits on the northern shore of Lake Trasimeno, offering picturesque views and a laid-back vibe. The village’s medieval Rocca dominates the skyline, and you can climb the 98-foot tower for panoramic vistas of the lake and its islands. It’s a wonderful spot for photographers and nature lovers.

Enjoy fresh lake fish at waterfront restaurants or take a boat trip to Maggiore or Polvese Island. Visit during the summer for lively jazz and blues festivals where you can listen to soulful live music late into the night.

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Passignano

9. Monteriggioni

A pretty town of fairy-tale towers

Monteriggioni medieval walled hilltop town.

Good for: Photo, History


Monteriggioni is one of Tuscany’s best-preserved medieval villages, known for its circular walls and 14 impressive towers. This compact town is easy to explore and offers a peaceful atmosphere, making it great for a quick visit or a day trip combined with Siena or San Gimignano. If you’re driving, Monteriggioni is accessible in about an hour from Florence.

Sample local wines at small enotecas or shop for handmade leather goods in the village boutiques. Walk the ramparts for fantastic views, join a local history tour to learn about the village’s defenses, and snap photos of the towers against the blue sky.

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Monteriggioni

10. Fiesole

A secluded hilltop village

View of Roman Amphitheater in Fiesole.

Good for: Photo, Couples, Food


Fiesole sits high above Florence and is famous for its breathtaking views of the city and the Arno Valley. This hilltop town is packed with history, from Roman ruins to an Etruscan museum and beautiful gardens. It’s an ideal half-day trip and easily reached by bus in just 20 minutes.

Stroll through the archaeological area to see the Roman amphitheater and temple, or relax in the lush gardens. Indulge in Tuscan pastries at local cafes or browse the small art galleries for a one-of-a-kind souvenir. Check out the antiques market on the first Sunday of the month if you’re looking for something truly special.

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Fiesole

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