Fun-Filled 5 Days: Cortona's Charming Delights Await!

Discover the charm and beauty of Cortona, Italy: a journey through history, art, and breathtaking landscapes.

28 August 2023

Cortona, Italy is a beautiful hilltop town located in the heart of Tuscany. Renowned for its stunning views of the surrounding countryside, this charming destination offers a perfect blend of history, culture, and gastronomy. From exploring historic sites such as the Etruscan Academy Museum to indulging in mouthwatering Tuscan cuisine, a visit to Cortona promises an unforgettable experience for any traveler.

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Travel plan

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Day 1

Welcome to Charming Cortona!

  • Check into the rustic and cozy Locanda I Grifi, a charming hotel with stunning views of the surrounding countryside.
  • Take a leisurely stroll through Piazza della Repubblica, the heart of Cortona, and soak up the buzzing atmosphere.
  • Indulge in a delicious lunch at La Grotta, a hidden gem serving mouthwatering Tuscan delicacies.
  • Explore the Etruscan Academy Museum, home to fascinating artifacts that tell the story of Cortona's ancient past.
  • Join a cooking class at Latteria Vecchia, where you'll learn to make the perfect pasta while sipping on local wine.
Day 2

Discover the Hidden Treasures

  • Embark on a scenic hike up to the impressive Medici Fortress for panoramic views of Cortona and the rolling hills of Tuscany.
  • Fuel up with a delightful breakfast at Bar del Teatro, where the cappuccinos are as beautiful as the art-filled surroundings.
  • Wander through the narrow cobblestone streets of Cortona's historic center, stumbling upon charming boutiques and artisan shops.
  • Visit the striking Cathedral of Santa Maria Assunta, an architectural masterpiece with magnificent frescoes.
  • Enjoy a leisurely dinner at Osteria del Teatro, where traditional Tuscan flavors meet innovative culinary techniques.
Day 3

Immerse Yourself in Tuscan Culture

  • Spend the morning exploring the enchanting Diocesan Museum, with its collection of religious art that will transport you back in time.
  • Unleash your inner artist at Tuscan Pottery, a ceramics workshop where you can channel your creativity and create a unique souvenir.
  • Savor a delicious lunch at Trattoria Dardano, a family-run gem offering delectable Tuscan dishes bursting with flavor.
  • Immerse yourself in the world of wine at Enoteca Molesini, where knowledgeable staff will guide you through a tasting of local vintages.
  • Dance the night away at Bar Bella Vista, a lively spot where locals and travelers come together to enjoy great music and vibrant atmosphere.
Day 4

A Day of Wineries and Olive Groves

  • Embark on a scenic drive through the Tuscan countryside, stopping to sample exquisite wines at Fattoria La Vialla.
  • Enjoy a leisurely picnic amidst a sea of olive trees at Tenuta Le Velette, reveling in the flavors of freshly pressed olive oil.
  • Explore the underground cellars of Avignonesi Winery, where you'll taste exceptional wines and learn about the winemaking process.
  • Satisfy your appetite with a rustic lunch at La Tufaia, a family-run trattoria known for its incredible homemade pasta.
  • Relax and unwind at Caffè del Teatro, with a refreshing Aperol Spritz in hand while taking in the charming views of Cortona.
Day 5

Farewell to Cortona

  • Start the day with a heavenly breakfast at Caffè Tuscher, known for its delectable pastries and artisanal coffee creations.
  • Take a scenic drive to Lake Trasimeno, where you can spend the day basking in the sun and indulging in delicious seafood.
  • Bid Cortona goodbye with a final dinner at Osteria del Borgo, savoring the flavors of traditional Tuscan cuisine with a modern twist.
  • End your stay on a sweet note with gelato from Snoopy Gelateria, offering a variety of mouthwatering flavors that will make your taste buds dance.
  • Pack your bags, filled with memories of Cortona's rustic charm and warm-hearted hospitality, ready for your next adventure.

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.

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Number of days

1 2 3 4 5

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

More travel plans

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Cortona: A Romantic Retreat of Delightful Discoveries

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Discover the Enchanting Delights of Cortona, Italy

Cortona, Italy, is a dreamy hilltop town that offers a perfect blend of history, art, and breathtaking landscapes. Explore its narrow streets, lined with charming houses and traditional shops, as you immerse yourself in the ancient Etruscan heritage. Visit the imposing Cortona Cathedral and the renowned Museo Diocesano to witness stunning works of art, then relish the panoramic views of the picturesque countryside from the medieval fortress, Fortezza del Girifalco.

Cortona: A 3-Day Journey of Cuisines, Art, and Adventure

Cortona, Italy is a charming hilltop town that offers a perfect blend of history, culture, and breathtaking landscapes. As a tourist, you can explore its narrow medieval streets, visit the impressive Etruscan city walls, and discover art treasures at the MAEC museum. Additionally, don't miss out on the opportunity to savor delicious Tuscan cuisine and wine while enjoying panoramic views of the picturesque valleys surrounding Cortona.