Cortona: A Vibrant 4-Day Adventure in Tuscany

Discover the enchantment of Cortona, where history, art, and beauty come to life.

28 August 2023

Cortona, Italy is a charming and picturesque hilltop town in the heart of Tuscany, perfect for any tourist seeking an authentic Italian experience. This ancient Etruscan town offers breathtaking views of the surrounding countryside, with its cobbled streets, historic landmarks, and delicious local cuisine. Visitors can explore its medieval architecture, wander through art galleries, and immerse themselves in the rich cultural heritage of this enchanting destination.

Save and get deals

Travel plan

Getting latest place information
Day 1

Ciao Cortona

  • Check into Hotel San Michele, a charming traditional villa with stunning views of the town
  • Start your day with a leisurely stroll through the cobblestone streets of Cortona, marveling at its medieval charm
  • Visit Museo Diocesano to get a crash course in local Etruscan history
  • Climb up to the magnificent Eremo delle Celle, a peaceful hermitage nestled in the hillside
  • Indulge in a hearty Tuscan lunch at Trattoria Dardano, where every bite feels like a warm hug
  • Spend the evening at Piazza Garibaldi, enjoying live music and sipping on a refreshing Aperol Spritz
Day 2

Art, Wine & Sunshine

  • Enjoy a leisurely breakfast at Osteria del Teatro, savoring their homemade pastries and aromatic Italian coffee
  • Immerse yourself in the world of Italian Renaissance at Museo Diocesano's impressive art collection
  • Embark on a wine tasting adventure at Fattoria Le Capezzine, where lush vineyards and delicious Chianti await
  • Soak up the Tuscan sunshine at Lago di Trasimeno, a picturesque lake perfect for a lazy picnic
  • Enjoy a candlelit dinner at Ristorante AD Braceria, where the flavors of Tuscany are elevated to new heights
Day 3

Exploring the Countryside

  • Rise and shine for an early morning hike to Le Celle, a peaceful monastery founded by Saint Francis of Assisi
  • Discover the rural beauty of Cortona's surrounding countryside on horseback with Agriturismo La Roverella
  • Satisfy your hunger with a lunch feast at Ristorante La Bucaccia, indulging in their famous pici pasta and wild boar ragu
  • Visit the impressive Cortona Cathedral, a striking example of Romanesque architecture
  • Wind down with a sunset aperitivo at Bar Del Teatro, while soaking in the panoramic views of the valley
Day 4

Indulge & Relax

  • Begin your day in style with a luxurious spa treatment at Hotel Villa Marsili, pampering your senses from head to toe
  • Take a leisurely stroll along the ancient city walls, embracing the breathtaking views of the Tuscan countryside
  • Enjoy a Tuscan cooking class at Tuscookany, where you'll learn to create mouthwatering Italian dishes to impress even nonna
  • Savor the flavors of Cortona at Osteria del Teatro, where every dish is a love letter to Tuscan cuisine
  • Bid farewell to Cortona with a glass of Vin Santo, a sweet dessert wine that perfectly encapsulates the essence of Tuscany

Length of stay

1 day 2 days 3 days 4 days 5 days

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

How to get there

Plane

The best way to reach Cortona by plane is to fly to Florence Airport (FLR) and then take a taxi or public transportation to Cortona.

Car

Driving to Cortona is a great option as it allows for flexibility and scenic views. You can rent a car at Florence Airport and take the A1 highway towards Rome, then exit at Valdichiana. From there, follow the signs to Cortona.

Train

To get to Cortona by train, you can take a train to Terontola-Cortona train station and then use local transportation or a taxi to reach the town center.

Boat

As Cortona is located inland, there are no direct boat routes available to reach the town.

Bus

Taking a bus from Florence to Cortona is a convenient option. You can catch a bus from Florence's main bus station and it will take you directly to Cortona.

Destination

Cortona

Nestled in the rolling hills, you'll find a charming town that's as picturesque as a postcard, but with more gelato and fewer pigeons. Welcome to a place where pizza is an art form and the locals are convinced that the leaning tower of Pisa is just a little tipsy.

 Save and get deals

Number of days

1 2 3 4 5

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

More travel plans

Cortona Unleashed: A Two-Day Budget Adventure

A trip to Cortona, Italy on a limited budget is a great choice for budget-conscious travelers looking to immerse themselves in history and culture. Explore the charming medieval town and its beautiful churches, museums, and cobblestone streets. Enjoy budget-friendly local cuisine, stroll through vineyards, and take in the breathtaking views of the Tuscan countryside without breaking the bank.

A Day Trip to Enchanting Cortona, Italy

Experience the romance of Cortona, Italy, as you and your partner immerse yourselves in the enchanting Tuscan countryside. Wander hand-in-hand through the narrow, cobblestone streets, adorned with picturesque medieval buildings and stunning views of the rolling hills. Indulge in delectable local cuisine, sip fine wines, and absorb the charm and tranquility of this idyllic destination, creating unforgettable memories for a truly romantic getaway.

Romantic Rendezvous: 5 Days in Enchanting Cortona

Experience the enchanting beauty of Cortona, Italy, on a romantic getaway. Nestled amidst captivating landscapes, this hilltop town offers breathtaking views of vineyards and olive groves. Immerse yourselves in the rich history, explore medieval streets hand in hand, and savor authentic Tuscan cuisine, creating memories that will last a lifetime.

Cortona Unleashed: The Ultimate 5-Day Budget Adventure!

Cortona, Italy offers a charming and affordable destination for travelers on a limited budget. With its hilltop position, picturesque streets, and lovely views of Tuscany's rolling hills, it provides a captivating experience without breaking the bank. From exploring historical sites and local markets to savoring delicious yet pocket-friendly Italian cuisine, Cortona truly offers a budget-friendly trip full of delightful surprises.