Ultimate Day Trip to Cortona Italy: Best Places to Visit, Eat, and Stay in Tuscany’s Hidden Gem

Cortona Italy day trip itinerary

Perched atop a hill in the stunning Tuscan countryside, Cortona is a charming town known for its medieval architecture, breathtaking views, and rich cultural heritage.

Featured in films like Under the Tuscan Sun, this ancient town offers a captivating blend of history and beauty that’s perfect for a day trip. In this guide, you’ll discover the top places to see, dine, and stay, ensuring an unforgettable experience in Cortona.

Cortona courtyard
Palazzo del Capitano Cortona
Cortona Italy

Morning: Exploring Historic Cortona Italy

Start your day by immersing yourself in Cortona’s historic center, where ancient sites and breathtaking views await.

Piazza della Repubblica and Palazzo Comunale

Begin at Piazza della Repubblica, the heart of Cortona, where locals and visitors alike gather to soak in the town’s vibrant atmosphere.

Here, you’ll find Palazzo Comunale, a striking medieval town hall with a grand staircase and beautiful facade. This bustling square is the perfect spot to start your journey and experience the energy of Cortona.

Museo dell’Accademia Etrusca e della Città di Cortona

Just a short walk from the piazza, visit the Museo dell’Accademia Etrusca e della Città di Cortona. This museum offers a fascinating look into Cortona’s Etruscan origins and features impressive artifacts, including ancient bronzes and ceramics.

The exhibits provide an insightful introduction to the area’s deep historical roots, setting the stage for your day of exploration.

Afternoon: Savoring the Cuisine and Scenic Views of Cortona Italy

After a morning of sightseeing, take a break to enjoy Cortona’s culinary offerings and scenic vistas.

Lunch at Ristorante Tonino

Head to Ristorante Tonino for an authentic Tuscan lunch. This beloved restaurant, with panoramic views over the valley, serves up classic dishes like pici al cinghiale (pasta with wild boar) and ribollita (Tuscan vegetable soup).

The warm atmosphere and quality dishes make it a great choice for a memorable meal in Cortona.

Basilica di Santa Margherita and Fortezza di Girifalco

After lunch, make your way to the Basilica di Santa Margherita, a beautiful church dedicated to Cortona’s patron saint. Located on a hilltop, the basilica offers breathtaking views of the valley and surrounding countryside.

From here, continue to Fortezza di Girifalco, an ancient fortress with panoramic views that reward the effort it takes to reach this hilltop landmark.

It’s an ideal spot to pause, relax, and capture some incredible photos of the Tuscan landscape.

Ham Sandwich Cortona
Streets of Cortona
Cortona Hills
Cortona Skyline

Evening: Winding Down with Dinner and a Relaxing Stroll

As the sun sets over the valley, Cortona’s streets take on a magical glow, perfect for a leisurely evening.

Dinner at Taverna Pane e Vino

Wrap up your day with dinner at Taverna Pane e Vino, a cozy, traditional restaurant known for its exceptional wine selection and rustic Tuscan fare. Try the crostini with liver pâté, followed by bistecca alla Fiorentina (Florentine steak). The welcoming atmosphere and carefully curated menu make it the ideal spot to end your day in Cortona.

Evening Stroll Around Cortona’s Streets

After dinner, take a peaceful stroll around Cortona’s cobblestone streets, enjoying the town’s quiet beauty as it winds down for the evening. Explore side streets, discover hidden corners, and take in the charm that makes Cortona so unique.

Cortona tower

Where to Stay in Cortona Italy

Whether you’re seeking budget accommodations or a luxury retreat, Cortona has something for everyone.

  • Budget-Friendly: Locanda Petrella – This cozy guesthouse offers charming, budget-friendly rooms in a central location, making it an excellent choice for travelers looking to save while enjoying a comfortable stay.
  • Mid-Range: Hotel San Luca – Overlooking the Valdichiana Valley, this well-appointed hotel combines comfort with beautiful views, providing a relaxing mid-range option with easy access to Cortona’s attractions.
  • High-End Luxury: Relais Chateaux Il Falconiere & Spa – For a luxurious experience, Il Falconiere offers an exquisite blend of historic charm and modern amenities. With a renowned spa and gourmet dining options, this Relais Chateaux property provides a true taste of Tuscan elegance.

Essential Travel Tips for Cortona Italy

Best Time of Year to Visit

  • Spring (April-May): Spring brings mild weather and blooming wildflowers, making it a picturesque time to visit.
  • Fall (September-October): With comfortable temperatures and fewer tourists, fall is ideal for exploring Cortona’s streets and countryside.
  • Summer (June-August): Although warmer and busier, summer brings festivals and outdoor events to Cortona, adding a vibrant energy to the town.

Currency, ATMs, and Credit Cards

Cortona, like the rest of Italy, uses the Euro (€). ATMs are available around the town center, particularly near major squares and tourist areas, and accept most international cards. Credit cards are commonly accepted in restaurants, hotels, and larger stores, though carrying some cash is advised for smaller purchases and cafes.

Getting Around Cortona

Cortona is best explored on foot, allowing you to fully enjoy its charming streets and views. The town’s size and layout make walking easy, though be prepared for some uphill stretches. Public buses and taxis are available for trips outside of town, but walking is ideal for absorbing Cortona’s ambiance.

Useful Italian Phrases for Your Visit

Learning a few Italian phrases can enhance your experience in Cortona:

  • Buongiorno – Good morning
  • Grazie – Thank you
  • Scusi – Excuse me
  • Quanto costa? – How much does it cost?
  • Dov’è…? – Where is…?
  • Un tavolo per due, per favore – A table for two, please
  • Il conto, per favore – The check, please

Cortona Italy Final Thoughts

Cortona’s blend of history, natural beauty, and Tuscan cuisine make it a captivating destination. This day-trip itinerary guides you through the highlights of Cortona, from historic landmarks and scenic viewpoints to the best local dining spots.

A day spent wandering Cortona’s enchanting streets is truly a journey through the heart of Tuscany.

Happy Traveling!

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