Tuscany road trip stage 1 Chianti and San Gimignano guide

Embarking on a road trip through Tuscany is a dream for many travelers, and the Chianti region is undoubtedly one of its crown jewels. Imagine rolling hills adorned with vineyards, charming medieval villages, and culinary delights waiting at every turn. In this guide, we will explore the enchanting landscapes and hidden gems of Chianti, offering you insights to make the most of your journey.

From Florence to the picturesque San Gimignano, this journey is a feast for the senses. Buckle up as we dive into the heart of Chianti, where every corner reveals a new wonder, and every moment is an opportunity to connect with the beauty of nature and history.

7 must-see attractions in Chianti

As we set out from Florence, the question on our minds was: how do we navigate out of the bustling city? The thought of getting lost or accidentally driving into the Arno made us chuckle nervously. However, once we hopped into our Fiat Punto, the adventure truly began.

Our first stop was none other than Piazzale Michelangelo, where we paused to take in the breathtaking panoramic view of Florence. With a final wave to the city, we hit the road, ready to explore the wonders that lay ahead.

1. Via Chiantigiana

One of the most scenic routes in the region is the Via Chiantigiana (SR22). This road winds gracefully through lush vineyards and picturesque landscapes, offering a true taste of what Tuscany has to offer. As we drove, we found ourselves enchanted by the sights: charming farmhouses, fields bursting with flowers, and the occasional stunning vista that made us stop and capture the moment.

Traveling along the Via Chiantigiana is an essential experience, as it allows you to appreciate the essence of Chianti beyond just its famous wines. Each bend in the road reveals a new postcard-worthy scene, and as we passed fellow travelers, we couldn't help but share the excitement of discovering this beautiful region.

2. Greve in Chianti

A short drive brought us to the heart of Chianti: Greve in Chianti. This quaint town is perfect for strolling through its historic streets, visiting the Church of Santa Croce, and exploring the Wine Museum. Although it's the largest town in the Chianti region, with around 14,000 residents, it maintains a charming, small-town atmosphere.

3. Montefioralle

Next, we ventured to the ancient village of Montefioralle, one of the most picturesque spots in Chianti. Known for its medieval castle, Montefioralle transports visitors back in time with its cobblestone streets and rustic charm. As we wandered through the village, we snapped countless photos, captivated by the beauty surrounding us.

Reaching Montefioralle required navigating a narrow, winding road, but the journey was worth it. The village's authenticity and the stunning views of the countryside are a testament to Chianti's enchanting allure.

4. Panzano in Chianti

Our next stop was Panzano in Chianti, historically significant and home to a beautiful castle that offers sweeping views of the landscape. We couldn't resist the opportunity to taste the local cuisine, especially at the famous Antica Macelleria Cecchini, where they serve the renowned fiorentina steak while reciting verses from Dante’s Divine Comedy.

5. Radda in Chianti

Continuing our journey, we explored Radda in Chianti, another delightful medieval town. Its well-preserved walls and charming streets invite leisurely exploration, giving visitors a glimpse into the region's rich history.

6. Castellina in Chianti

Feeling a bit peckish, we made a stop at Castellina in Chianti, a lovely town perched on a hill with Etruscan origins. Here, we savored delicious pappardelle with wild boar ragu and a savory beef stew. The combination of flavors was a true highlight of our trip. This culinary stop reinforced the idea that one of the best ways to explore Chianti is through its food.

7. San Gimignano

After a satisfying meal, we set our sights on the crown jewel of our Chianti adventure: San Gimignano, often referred to as the "Manhattan of the medieval times" due to its iconic towers. This enchanting town captured our hearts from the moment we arrived, with its tranquil rural vibes and stunning architecture.

The town is renowned for its 14 towers, remnants of a time when noble families competed for prestige. Once, there were as many as 72 towers, each symbolizing power and wealth. Today, the town exudes charm, especially at dusk, when the crowds disperse and the streets fill with a serene ambiance. We stayed overnight, soaking in the magic of San Gimignano as the sun set, creating a perfect backdrop for our first day in Tuscany.

Exploring the Chianti region: essential tips

To make the most of your journey through Chianti, consider the following tips:

• Best time to visit: Spring and fall offer pleasant weather and fewer crowds.
• Plan your route: Know which towns you want to visit to maximize your time.
• Stay flexible: Allow time for spontaneous stops along the way.
• Tasting local wines: Don't miss the chance to sample Chianti's renowned wines.

Map of the Chianti route

Here’s a simple map of our route through the Chianti region, highlighting the major stops along the way:

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Dining options in Chianti

While exploring Chianti, culinary experiences are a must. We enjoyed a delightful meal at the Chianti Bar in Castellina, where we savored traditional Tuscan dishes. However, for a more authentic experience, consider dining at an agriturismo in the area, where you can enjoy home-cooked meals made from local ingredients.

In San Gimignano, be sure to try the gelato from gelateria Dondoli, known for some of the best gelato in the world. A cone with two flavors and a dollop of whipped cream is a refreshing treat after a long day of exploring!

Accommodations in San Gimignano

For those looking to stay overnight, we recommend Fattoria Guicciardini, located in the historic center. The ambiance and proximity to major attractions make it an excellent choice for travelers.

As we conclude our first chapter in Chianti, we are left with memories of breathtaking views, delicious food, and the warm hospitality of the locals. This journey through Tuscany is just the beginning of our Italian adventure, and we can’t wait to see what the next leg has in store.

For more travel inspiration and detailed itineraries, check out this engaging video that showcases the beauty of Tuscany:

We hope our journey through Chianti ignites your wanderlust and inspires you to explore this enchanting region for yourself!