Roadtrip through Italy: Explore hidden gems in Tuscany!

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Our journey begins in Florence and spans four unforgettable days. Let our recommendations inspire you as you explore some of the most scenic roads in Tuscany.

If you're still looking for the perfect car to complete your adventure, take a look at our fleet. Alongside budget-friendly options, our lineup features an incredible selection of sports cars and convertibles, including the new Porsche 911, Audi R8, Aston Martin Vantage, and Ferrari Roma.

Table of Contents

Our Tuscany Road Trip Begins: Getting to Florence

How you get to Florence is entirely up to you. You can drive your own car or rent one of our premium vehicles directly from one of our rental stations – just be sure to allow at least one day each for the journey there and back. Alternatively, you can take a convenient flight, check into your hotel, and we’ll deliver your car straight to your accommodation in Florence.

The road trip itself covers approximately 550 kilometers, excluding travel to and from Florence. As of October 2024, the drive to Florence without breaks takes about 7 hours, depending on traffic. That’s why we recommend a stopover between Bolzano and Verona.

Along our route, we’ll visit Siena, San Casciano dei Bagni, and Castelfiorentino – and, of course, we won’t take the direct route. Instead, we’ve planned a journey packed with winding roads and breathtaking landscapes.

Italian Road Trip: 4 Days of Thrilling Curves – Starting in Florence

We wake up in one of Italy’s most beautiful cities: Florence. This historic gem is just waiting to be explored. We find ourselves in the heart of a cultural hotspot, surrounded by world-famous landmarks, paintings, and museums that tell stories of times long past.

But the real adventure begins once we leave the city. Our journey takes us to one of the most stunning roads in Tuscany: the Chiantigiana (SR222). To make it easier for you to find, we’ve linked the route for you here. This winding road snakes through the heart of Chianti, a region known for its breathtaking vineyards and lush cypress groves. We drive through this incredible landscape, breathing in the fresh Tuscan air and reveling in the sense of freedom these seemingly endless roads provide.

First Stop: Greve in Chianti. Once home to the Etruscans and Romans, this charming town is more than just a historical site – it’s the gateway to a world of culinary delights and a paradise for food lovers. Continuing through the rolling hills, we experience how the road constantly changes, revealing new vistas and surprises at every turn.

In Castellina, we stop for a delicious Tuscan lunch at a rustic countryside estate nestled among the hills. Afterward, we head to Radda (SR429), where we admire the vast landscape from its ancient city walls. Of course, a stop at Castello di Brolio on the SP484 is a must – the views are simply breathtaking.

By the afternoon, we reach Siena via the SP408, where the charming old town with its narrow streets and stunning piazzas awaits us. As evening falls, Siena comes to life, and we take our time to soak in the unique atmosphere of this Tuscan treasure.

If you’re still looking for a hotel, we recommend Hotel Certosa Di Maggiano. Not only does it offer free private parking, but this 700-year-old former monastery allows guests to stay in converted monk’s quarters. Plus, it’s just 2 km from Siena’s famous Piazza del Campo.

Tuscany Road Trip: From Siena to San Casciano dei Bagni

After a restful night in the Siena area, today’s journey takes us to the Val d'Orcia, a region that enchants visitors with its rolling hills and picturesque villages. We start the day with a healthy breakfast and set off a little earlier to have the roads all to ourselves. Here’s the route for you.

The first stop on our route is Pienza. Following the SP12, SP60, SP14, and SP71, we reach Pienza, a UNESCO World Heritage Site that feels like a step back in time. We admire the architecture, wander through the narrow streets, and take in the stunning views of the countryside. Next, we head to Montalcino, near the majestic Monte Amiata, an extinct volcano with natural hot springs.

Following the SP12, SP60, SP14, and SP71, we reach Pienza, a UNESCO World Heritage Site that feels like a step back in time. We admire the architecture, wander through the narrow streets, and take in the stunning views of the countryside.

Next, we head to Montalcino, near the majestic Monte Amiata, an extinct volcano with natural hot springs.

Next Stop: Castelfiorentino – Road Trip Through Northern Italy

Can’t get enough of Tuscany’s scenic roads? Keep going and chase the perfect curve – whether you follow our planned route or take a few unexpected detours, you might stumble upon a hidden cypress grove or a charming winery where you can pick up a bottle as a souvenir. To make navigation easy, we’ve linked the standard route.

We continue along the SP321, passing through La Valletta, Bagnolo, and Arcidosso. Then, we follow the Strada Provinciale Cipressino to Paganico, take the SP48, which connects to the SP157, and merge onto the SP73bis. Once we reach Frosine, we turn onto the SP541. No matter how challenging the drive has been, it’s worth it! The stunning Belmond Castello di Casole invites us to pause for a delightful lunch. This exclusive retreat provides an unforgettable backdrop for photos – just call ahead to avoid accidentally crashing a wedding!

Once we’re ready to hit the road again, we follow the SP541 north. In Colle di Val d’Elsa, we turn west onto the SP36 before merging onto the Strada Provinciale 1, Via San Gimignano. Here, we let the engine roar and soak in the breathtaking scenery as our tires glide over winding roads – no wonder this region is part of the legendary Mille Miglia rally! Our next stop, San Gimignano, is another UNESCO World Heritage Site. We take time to unwind with a glass of wine and enjoy the incredible atmosphere.

Continuing on the SP95 toward Castelfiorentino, we have one last chance to explore Certaldo, a charming town worth a quick detour. Tonight, we check into Le Case Di Camin Bianco, a dreamy Tuscan retreat. Whether we watch the sunset from the outdoor pool or sip a drink on the terrace, we end the evening with a delicious dinner, followed by a well-earned night’s rest.

Back to Florence: The Final Stages of the Sports Car Experience

Before diving back into the vibrant buzz of Florence, we have one last stretch of asphalt ahead of us, winding through the breathtaking Tuscan landscape (you can check the exact route on Google Maps). As the road calls us once more, we follow it north via the SP16. Our first stop is Vinci, the birthplace of the great polymath Leonardo da Vinci, before continuing to Pistoia.

When we finally reach Florence via the A11, the city still has plenty to offer. If you have the energy, you might even want to visit "The Mall," an impressive shopping center. The four must-see sights in Florence are the Florence Cathedral, the Uffizi Gallery, the Ponte Vecchio, and the Galleria dell’Accademia. The cathedral’s stunning dome dominates the city skyline and offers breathtaking views. At the Uffizi, you can admire Renaissance masterpieces, while the Ponte Vecchio, with its charming goldsmith shops, exudes a unique charm. And, of course, Michelangelo’s famous "David" in the Galleria dell’Accademia is an unforgettable highlight.

The Journey Home: Time to Head Back!

Just like at the start of your trip, you’re completely free to choose how you return home. If you’re traveling in your own car, this is obvious, but even with one of our rentals, you remain flexible.

Depending on your arrangement, you can simply leave the car at your hotel and fly home – our rental agents will pick it up in Florence. Of course, you’re also welcome to drive it back to one of our rental hubs in Munich, Frankfurt, Stuttgart, or even Hamburg or Berlin.

We hope you enjoyed our road trip guide – maybe it even inspired you to try the route yourself! If you're still looking for the perfect car, check out our fleet. We offer high-quality convertibles at fair prices, including the BMW 4 Series, the timelessly beautiful Porsche 911, nimble sports cars like the Alpine A110, and the powerful Audi R8.

For the ultimate Italian experience, the Ferrari Roma is your perfect match.