From Cortona to the Countryside: 5 Incredible Day Trips in Tuscany

Tuscany is a treasure trove of stunning landscapes, rich history, and culinary delights. Exploring beyond the charming hilltop town of Cortona allows visitors to uncover hidden gems nestled in the Tuscan countryside. Whether you are a history buff, a wine enthusiast, or simply seeking tranquility, these five incredible day trips from Cortona Italy will immerse you in the beauty and culture of Tuscany.

1. Montepulciano: A Wine Lover's Paradise

Perched high on a hilltop, Montepulciano is a medieval gem renowned for its exquisite Vino Nobile di Montepulciano. The journey from Cortona to Montepulciano takes approximately 40 minutes, making it an ideal day trip.

Highlights:

  • Wine Tasting Tours: Visit historic wine cellars, such as Cantina Contucci, where you can sample some of the finest local vintages.

  • Piazza Grande: Marvel at the grandeur of this square, surrounded by Renaissance palaces and the Cathedral of Santa Maria Assunta.

  • San Biagio Church: A masterpiece of Renaissance architecture, this church is set against the backdrop of rolling vineyards.

Insider Tip: Plan your visit during September to witness the grape harvest and indulge in local wine festivals.

2. Siena: The Medieval Marvel

A UNESCO World Heritage Site, Siena is a must-visit destination for history enthusiasts. The drive from Cortona to Siena takes about 1.5 hours, offering scenic views of the Tuscan countryside.

Highlights:

  • Piazza del Campo: Known for its unique shell shape, this historic square hosts the famous Palio horse race.

  • Siena Cathedral (Duomo di Siena): Adorned with intricate marble facades, this cathedral is a masterpiece of Gothic architecture.

  • Torre del Mangia: Climb this iconic tower for panoramic views of the city and beyond.

Insider Tip: Don’t miss tasting Siena’s traditional sweets like panforte and ricciarelli.

3. Arezzo: Art and Antiques Haven

Located just 30 minutes from Cortona, Arezzo is a city steeped in art, history, and tradition. It is less crowded than other Tuscan towns, offering a more relaxed experience.

Highlights:

  • Basilica of San Francesco: Admire Piero della Francesca’s fresco cycle, “The Legend of the True Cross.”

  • Piazza Grande: This sloping square is surrounded by stunning medieval architecture and hosts the monthly Antique Fair.

  • Roman Amphitheatre: A glimpse into Arezzo’s ancient past, this site is perfect for history enthusiasts.

Insider Tip: Time your visit to coincide with the Giostra del Saracino, a historic jousting tournament held in June and September.

4. Val d’Orcia: A Scenic Escape

The Val d’Orcia is a UNESCO World Heritage Site that epitomizes the picturesque beauty of Tuscany. This region, about an hour from Cortona, is famed for its rolling hills, cypress-lined roads, and quaint villages.

Highlights:

  • Pienza: Dubbed the “Ideal City” of the Renaissance, Pienza offers breathtaking views and delicious Pecorino cheese.

  • Bagno Vignoni: A unique village centered around a thermal pool used since Roman times.

  • Cypress Roads: Drive or bike along the iconic cypress-lined roads for unforgettable vistas.

Insider Tip: Capture the sunrise or sunset in the Val d’Orcia for postcard-perfect photographs.

5. Lake Trasimeno: A Tranquil Retreat

Just 20 kilometers from Cortona, Lake Trasimeno offers a serene escape from the bustling towns and cities. This vast lake, Italy’s fourth-largest, is perfect for nature lovers and outdoor enthusiasts.

Highlights:

  • Isola Maggiore: Take a ferry to this charming island, known for its lace-making tradition and peaceful ambiance.

  • Watersports: Enjoy kayaking, sailing, or paddleboarding on the lake’s calm waters.

  • Local Cuisine: Savor lake fish specialties at traditional trattorias along the shoreline.

Insider Tip: Visit in spring or early autumn to avoid crowds and enjoy mild weather.

Practical Tips for Planning Your Day Trips

  • Transportation: Renting a car is the most convenient way to explore Tuscany, as it allows flexibility and access to remote areas.

  • Timing: Start your trips early in the morning to make the most of your day.

  • Local Guides: Consider hiring a local guide for deeper insights into the history and culture of each destination.

Conclusion

From the wine cellars of Montepulciano to the tranquil shores of Lake Trasimeno, Tuscany offers an abundance of experiences for every traveler. Each destination near Cortona unveils a unique facet of this enchanting region, leaving visitors with unforgettable memories. Whether you seek history, nature, or gastronomy, these five day trips promise a journey into the heart of Tuscany’s charm.

Looking to explore the best of Tuscany? Classic Tuscany offers unforgettable day trips from Cortona, Italy and exclusive private wine tours across the region. Whether you want to discover hidden gems or indulge in Tuscany's finest wines, we’ll craft the perfect experience for you. Ready to embark on a memorable journey through Tuscany with Classic Tuscany? Let us guide you to an extraordinary adventure!

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