Millions of readers and movie fans fell in love with Tuscany through Frances Mayes’ bestselling memoir and the Hollywood film Under the Tuscan Sun. In the story, the golden light, cinematic hills, and romantic slow place captured the imagination of travelers worldwide. But where is this dreaming place and what is the real borgo like when you step past the movie screen?
Perched dramatically on a hilltop nearly 500 meters above sea level in the Val di Chiana, Cortona is far more than a cinematic backdrop. It is a living, breathing hilltop town with over two millennia of history. While Hollywood highlighted its dreamy, postcard-perfect romance, the true magic of Cortona in 2027 lies in its authentic rhythm: bustling medieval squares, ancient Etruscan stone walls, quiet cobbled alleys and authentic local life.
Discovering Cortona’s Historic Heart and Iconic Landmarks
To truly experience Cortona, start where local life unfolds daily: Piazza della Repubblica. Framed by the grand Palazzo Comunale with its iconic staircase and the historic Palazzo del Capitano del Popolo, this lively square remains the beating heart of the town. Just steps away, Piazza Garibaldi opens up to sweeping, panoramic views stretching across the Val di Chiana all the way to Lake Trasimeno in neighboring Umbria.
Cortona’s cultural heritage runs deep into antiquity with the Etruscan and Roman Legacy. The MAEC (Museo dell'Accademia Etrusca) preserves incredible Etruscan artifacts and ancient treasures discovered across the region. Surrounding the town are impressive 3-kilometer-long Etruscan walls and ancient noble tombs scattered throughout the valley.
In addition, the Diocesan Museum displays priceless Renaissance artworks, while the peaceful Franciscan Hermitage "Le Celle", nestled in a quiet ravine outside the walls, offers a tranquil retreat. Furthermore, walk up to the highest point of the town to visit the Basilica of Santa Margherita and the imposing Girifalco Fortress, where the views of the surrounding countryside are unbeatable.
What to Do in Cortona in 2027
Whether you are spending a weekend or a longer vacation, Cortona offers an ideal blend of culture and relax. Stroll along the narrow cobbled streets lined with artisan shops and traditional trattorias. Pair rich Tuscan cuisine with a glass of Cortona’s celebrated Syrah wine.
Or allow yourself to get lost in the steep, winding streetlets (vicoli) that showcase Cortona's authentic medieval architecture. In addition, you can explore the Tuscan countryside using Cortona as your base to tour the olive groves, vineyards, and rolling hills of the Val di Chiana.
Furthermore, in 2027, Cortona will celebrate the 300th anniversary of the founding of the MAEC - Museum of Etruscan Academy with events and initiatives that will involve the town throughout the entire year.
Cortona: celebrate your love with a dream wedding in
To complete your dream Tuscan holiday, finding the right base in the countryside makes all the difference. Located just a short distance from the historic village, Villa Ivana offers an extraordinary 17th-century historic residence surrounded by a romantic park of centuries-old trees and stunning valley views.
Featuring refined frescoed suites equipped with modern comforts—including jacuzzis, a private sauna, and a large outdoor swimming pool overlooking the hills of Cortona—Villa Ivana is designed for romantic getaways and unforgettable stays in true Tuscan style.
Beyond luxurious holidays, Villa Ivana serves as an ideal setting for dream weddings, gala dinners, and special events. With its elegant reception halls and manicured Italian gardens accommodating up to 200 guests, it provides a fairytale backdrop for exchanging vows with sweeping views of the Val di Chiana.
CLICK HERE TO BOOK YOUR HOLIDAY AT VILLA IVANALocalità Ossaia, 51, 52044 Cortona AR
About the author

Sara Celin
Discover Cortona, the real under the Tuscan sun town.