Tuscany is a dream destination for anyone who loves rolling hills, medieval villages, and breathtaking landscapes. Its combination of art, culture, and nature makes it one of the most picturesque regions in Italy. From Florence’s historic streets to the rustic charm of the Chianti countryside, driving through Tuscany is more than just travel—it’s an experience that will linger in your memory.

Whether you’re planning a short road trip or a long journey, these 15 scenic drives offer unforgettable views, hidden gems, and activities you truly need to see. Based on my overall experience, these routes will help you explore Tuscany in a way that goes beyond the usual tourist spots. Let me take you on a journey you’ll genuinely enjoy.

1. Florence to Fiesole: Art, Hills, and Sunset Views

Starting your Tuscan road trip in Florence? A short drive to Fiesole is perfect for combining city life with nature. Just a 20-minute drive from central Florence, the hilltop town of Fiesole offers panoramic views of the city, ancient Roman ruins, and charming streets to wander.

Things to do along the route:

  • Stop at Piazzale Michelangelo for iconic sunset views.
  • Explore the Roman amphitheater and Etruscan ruins in Fiesole.
  • Enjoy a local coffee or gelato in a small café overlooking Florence.

This route is short but rich with history and stunning vistas, making it ideal for the first day of your Tuscan adventure.

2. Florence to Chianti: Rolling Hills and Wine Tastings

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The drive from Florence to the Chianti region is one of Tuscany’s most famous routes. As you leave the city, vineyards, olive groves, and cypress-lined roads create a postcard-perfect landscape.

Must-see stops:

  • Greve in Chianti: Famous for its wine and local markets.
  • Castellina and Radda: Explore medieval streets and quaint shops.
  • Wine estates: Taste Chianti Classico and tour historic cellars.

From my own personal experience, stopping at small wineries off the main roads gives the most authentic taste of Tuscan wine culture.

3. Siena to San Gimignano: Medieval Towns and Panoramic Views

This drive takes you through some of Tuscany’s most famous medieval towns. The route winds through vineyards and rolling hills, with the towers of San Gimignano visible from miles away.

Highlights:

  • Siena’s Piazza del Campo: Iconic for its shell-shaped square and historic buildings.
  • Monteriggioni: A small walled village perfect for a short walk.
  • San Gimignano: Known as the “Town of Fine Towers,” ideal for tasting local gelato.

This route offers a perfect mix of history, food, and scenery. Don’t rush—stop frequently to soak in the views.

4. Val d’Orcia Drive: Iconic Rolling Hills

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Val d’Orcia is the quintessential Tuscany landscape: gentle hills, golden fields, and cypress trees lining narrow roads. Driving here feels like traveling through a painting.

Must-see places along the drive:

  • Pienza: Famous for pecorino cheese and Renaissance architecture.
  • Montalcino: Home of Brunello wine and charming medieval streets.
  • Bagno Vignoni: A unique village with a thermal water pool in the main square.

From my overall experience, the magic of Val d’Orcia is in the small detours. Even a tiny side road can lead to a postcard-perfect hilltop view.

5. Florence to Lucca: Art, History, and Enchanting Streets

Heading west from Florence, Lucca offers a blend of medieval charm and lush countryside. Its city walls are perfect for walking or cycling, and the drive itself features scenic landscapes and quaint villages.

Highlights:

  • Lucca’s city walls: Walk or bike around the Renaissance-era walls.
  • Torre Guinigi: Climb this tower for stunning views of the city.
  • Nearby villages: Stop at small towns for local pastries and coffee.

The journey to Lucca is as enjoyable as the destination, with endless opportunities to pause and enjoy the scenery.

6. Pisa and the Countryside Beyond: More Than the Leaning Tower

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Most people drive to Pisa only for the Leaning Tower, but the surrounding Tuscan countryside is equally breathtaking. Small roads take you past olive groves, vineyards, and rivers.

Highlights:

  • Pisa’s Piazza dei Miracoli: Iconic sights including the tower and cathedral.
  • Volterra: A medieval town with Etruscan history and stone streets.
  • Coastal detours: Drive toward the Tuscan coast for beaches and cliffs.

This route shows that Tuscany’s beauty isn’t just inland—it extends to the sea.

7. Florence to Arezzo: Art, History, and Lesser-Known Gems

Arezzo is often overlooked by travelers, but its streets, squares, and art make it a worthy drive from Florence. Along the way, rolling hills and peaceful villages provide endless photo opportunities.

Highlights:

  • Piazza Grande in Arezzo: Stunning medieval square with historic buildings.
  • Cortona detour: Famous for its hilltop views and Tuscan charm.
  • Antique markets: If visiting on the first Sunday of the month, enjoy a vibrant local market.

Driving here gives you a sense of authentic Tuscany, away from crowded tourist paths.

8. Florence to Volterra: Etruscan Heritage and Hillside Views

Volterra is a walled hilltop town with Etruscan history and alabaster crafts. The winding roads to Volterra offer endless landscapes that are worth every minute.

Highlights:

  • Etruscan museum and ruins: Step back in history.
  • Alabaster workshops: See local artisans at work.
  • Hilltop viewpoints: Capture sweeping views of the Tuscan valleys.

From my own personal experience, arriving in Volterra in the late afternoon gives the best light for photos and a serene atmosphere.

9. Florence to Cortona: Sunsets and Hidden Villages

The drive to Cortona is filled with charming villages, olive groves, and vineyard-lined roads. Cortona itself is a hilltop town made famous by literature and films.

Highlights:

  • Walk the ancient streets and discover artisan shops.
  • Enjoy sunset from Piazza della Repubblica for panoramic views.
  • Explore surrounding villages for authentic Tuscan cuisine.

Cortona is perfect for those who love combining scenery with history and local culture.

10. Chianti to Montepulciano: Wine Roads and Picturesque Hills

This route is ideal for wine lovers. Montepulciano, perched on a hill, is famous for Vino Nobile wine. The drive through Chianti’s countryside features vineyards, olive groves, and charming towns.

Highlights:

  • Wine tasting at local estates.
  • Explore Montepulciano’s medieval streets.
  • Stop at small roadside cafés for a break with views.

The mix of gastronomy and landscape makes this drive unforgettable.

11. Florence to Prato: Hidden Gems and Historic Sites

A short drive northwest of Florence, Prato offers historic streets, castles, and less crowded scenery.

Highlights:

  • Castello dell’Imperatore: Medieval fortress with rich history.
  • Textile museum: Learn about Prato’s famous textile heritage.
  • Surrounding hills: Explore tiny villages and scenic viewpoints.

This route gives a quieter, more local perspective of Tuscany.

12. Lucca to Garfagnana: Mountain Roads and Natural Beauty

If you love mountain scenery, the drive from Lucca to Garfagnana is a must. Forested valleys, winding roads, and mountain views make it a refreshing change from rolling hills.

Highlights:

  • Barga: A charming town with panoramic views.
  • Castiglione di Garfagnana: Explore small medieval streets.
  • Hiking opportunities: Numerous trails for nature lovers.

From my own personal experience, the winding roads here are perfect for travelers who enjoy combining driving with outdoor adventures.

13. Florence to Mugello: Nature, Villages, and Serenity

Heading north of Florence, Mugello is a hidden gem known for serene landscapes and historic villas.

Highlights:

  • Visit Villa Medicea del Trebbio: A Medici-era villa surrounded by greenery.
  • Explore local villages and cafes.
  • Scenic countryside drives with fewer crowds.

This route is ideal if you want peace and authentic Tuscan charm without heavy tourist traffic.

14. Siena to Monte Amiata: Mountains and Medieval Towns

Monte Amiata, a dormant volcano, offers a unique landscape in southern Tuscany. The drive from Siena takes you through forests, hills, and historic villages.

Highlights:

  • Abbadia San Salvatore: Explore this medieval town.
  • Monte Amiata viewpoints: Panoramic views of valleys and peaks.
  • Seasonal experiences: Snow in winter or lush green landscapes in summer.

This route combines natural beauty with history, offering a less conventional Tuscan experience.

15. Florence to the Tuscan Coast: From Hills to Sea

For those who want variety, the drive from Florence to the Tuscan coast is a journey from city streets to rolling hills and finally the Mediterranean Sea.

Highlights:

  • Explore coastal towns like Livorno or Viareggio.
  • Enjoy fresh seafood with a view.
  • Stop at countryside villages along the way for scenic breaks.

This route gives the perfect balance of inland beauty and coastal charm, showing Tuscany’s diversity.

Final Thoughts

Tuscany offers a variety of scenic drives that cater to every traveler’s taste. From rolling hills to medieval towns, vineyards, and coastal views, each route has something unique to offer. Based on my overall experience, taking your time and exploring side roads will reveal hidden gems that make these drives truly unforgettable.

Whether you’re chasing sunsets, tasting local wine, or wandering through historic streets, these 15 drives will help you experience Tuscany in a way that goes beyond the guidebooks. Prepare your playlist, grab your camera, and enjoy every moment of the Tuscan adventure.