5-Day Road Trip Through Tuscany Itinerary

Begin your day by exploring the Siena Civic Museum (Museo Civico di Siena), located in the Palazzo Pubblico. This museum houses an impressive collection of Sienese art and frescoes that depict the city's rich history.

Visit the iconic Palio of Siena (Palio di Siena), a traditional horse race held twice a year in Piazza del Campo. Even if you're not visiting during race time, you can still explore this historic square and learn about its significance.

Dine at Ristorante Arnolfo, offering contemporary Italian cuisine with stunning views over the Tuscan countryside. A perfect spot to savor local flavors while enjoying the serene landscape.

Drive through the picturesque Chianti region and stop at Brolio Castle (Castello di Brolio). This historic castle offers tours of its beautiful gardens, vineyards, and wine cellars, providing an immersive experience into Tuscan winemaking traditions.

Continue your journey to Castle of Meleto (Castello di Meleto). Explore this medieval fortress, enjoy wine tastings, and take in panoramic views of the surrounding countryside.

Enjoy dinner at Osteria di Passignano, nestled within an ancient abbey. The restaurant is renowned for its farm-to-table approach, offering dishes made from locally sourced ingredients.

Start your day by visiting the Lucca Clock Tower (Torre delle Ore). Climb to the top for breathtaking views over Lucca's historic center.

Explore Lucca's charming streets and visit Church of San Michele in Foro (Chiesa di San Michele in Foro), a stunning example of Romanesque architecture located in one of Lucca's main squares.

Dine at Borgo San Jacopo back in Florence on your return journey from Lucca. Located along the Arno River, this restaurant offers refined Italian dishes with picturesque river views.

Begin your day with a visit to Val d'Orcia. This UNESCO World Heritage site is renowned for its stunning landscapes, rolling hills, and picturesque villages. Take a leisurely drive through the region, stopping to admire the breathtaking views and capture some memorable photos.

Head to Montalcino, a charming hilltop town famous for its Brunello di Montalcino wine. Explore the town's historic center, visit local wineries for tastings, and enjoy a relaxing lunch at one of the quaint cafes.

For dinner, make your way to Il Falconiere, located in nearby Cortona. This Michelin-starred restaurant offers an exquisite dining experience with dishes crafted from locally sourced ingredients and paired with exceptional wines. A perfect way to conclude your Tuscan road trip.