Best things to do in Cortona Italy: Tuscan Sun Travel Guide

Some towns feel like postcards, Cortona feels like the whole album. Perched high above the Valdichiana Valley, this Tuscan charmer mixes medieval walls, café-lined piazzas, and sunsets that make you want to stay forever. You might know it from Under the Tuscan Sun, but the real magic comes from wandering its stone alleys, clinking glasses of local red, and stumbling upon views that stop you in your tracks. It’s the perfect balance of culture, food, and dolce vita. Sprinkle in unforgettable Tuscany wine tours, and you’ve got more than a trip, you’ve got a love affair with Tuscany. Ready to dive in? Here’s your guide to the must-see things to do in Cortona.

Top things to do in Cortona Italy

Start at Piazza della Repubblica

Start your Cortona journey in Piazza della Repubblica, the lively heart of town, where centuries-old palaces set the stage for daily life. Just around the corner, Piazza Signorelli adds a splash of Renaissance flair with exhibitions and cultural events that keep the atmosphere buzzing. Exploring these lively squares is one of the most memorable things to do in Cortona, a mix of history, people-watching, and Tuscan charm rolled into one.

Explore the Museo dell’Accademia Etrusca

Step into the Museo dell’Accademia Etrusca and you’re face to face with Cortona’s ancient soul. Think quirky treasures, mysterious statues, and even a bronze chandelier that’s been hanging around since the 5th century BC. It’s the kind of place where history suddenly feels playful, and wandering the halls is as much about curiosity as it is about culture. Plus, it’s right in Piazza Signorelli, so you can pop in between a coffee and your next gelato.

Walk to the Basilica di Santa Margherita

Climb up to the Basilica di Santa Margherita and you’ll be rewarded with views that make the hike worth every step. Perched above Cortona, this church feels both grand and peaceful, a place where stained glass catches the light and quiet corners invite you to pause. Step outside and the Tuscan hills roll out in front of you, the kind of view that begs for a deep breath (and a photo or two).

Climb to the Fortress of Girifalco

Hike your way up through Cortona’s winding alleys, and the Girifalco Fortress greets you at the top like a reward. The climb might get your legs working, but the payoff is unbeatable, 360° views over rooftops and rolling Tuscan hills. It’s one of the must-see things to do in Cortona, especially if you love a good mix of history, exercise, and jaw-dropping scenery.

Admire the symmetrical Calcinaio Church

Just outside Cortona’s walls sits the Calcinaio Church, a Renaissance beauty with strikingly clean lines and perfect symmetry. The walk down to it is half the experience: olive groves, open skies, and the town shrinking behind you. Step inside and you’ll find a cool, calm interior that feels worlds away from the busy piazzas above. It’s a peaceful pause, with architecture so balanced it almost feels like it was designed for pure serenity.

Top things to do around Cortona Italy

Live the vine life

Slip into a dreamy escape at Viandante Del Cielo, perched on the gentle hills near Lake Trasimeno in Umbria, where you get more than just wine, you get vibe. The restored 16th-century Convent feels like your own slice of calm; terraces slope down toward the lake, olive trees whisper in the breeze, and the vineyards weave in through the landscape. Book the Classic or Exclusive experience and you’ll wander among vine rows, taste three wines plus extra-virgin olive oil, and wrap it all up with a light meal and homemade bread.

Taste tradition

Tenute di Fraternita feels like stepping into Tuscany’s soul, where organic vineyards meet centuries of public history. The estate spans woods, fields, olives, and grapes, all cared for with respect for nature and the past. Join a tasting experience, wander among vine-strewn hills, and enjoy wines and olive oil that tell a story of place

Explore the roads of Montepulciano

A scenic day trip from Cortona, 45 minutes by car, brings you to Montepulciano, a Renaissance jewel perched on a hilltop with sweeping views over the Valdichiana Valley. Stroll through its elegant piazzas, step inside centuries-old palazzos, and let the town’s mix of art and history draw you in. You’ll still want to stop by the celebrated Montepulciano wineries, but the real charm comes from wandering cobbled streets, pausing in sunlit squares, and soaking in the timeless atmosphere.

For more inspiration, explore our guide to the best things to do in Montepulciano, this is one Tuscan hill town you’ll never forget.

Unwind with Tuscan flavors

Step into Fattoria Svetoni and let Tuscany slow you down: vineyards stretch along gentle slopes, olive trees hum in the breeze, and centuries of wine-making whisper in every corner. Tours lead you through an old cellar lined with oak barrels, where Sangiovese grapes tell tales of sunsets and soil. After tasting, linger under the sky with a light snack, enjoy the soft glow of sunset across Montepulciano views, and soak in the calm that comes when you get away from calendars and clocks.

Walk in the streets of Arezzo

40 minutes from Cortona, Arezzo bursts with energy and elegance all at once. This is a place where antique markets spill into Piazza Grande, frescoes by Piero della Francesca glow inside San Francesco, and every street feels like a film set waiting for you to wander in. Climb up to the Medici Fortress for sweeping views, then reward yourself with a lazy glass from one of the nearby Arezzo wineries. It’s a city that mixes art, history, and everyday Tuscan life into one irresistible package.

Want the full picture? Dive into our guide to the best things to do in Arezzo and see why this stop belongs on your Tuscany journey.

Drive to Pienza

About 50 minutes from Cortona, Pienza greets you with streets that smell of pecorino and windows filled with handmade goods. The main square is alive with people sipping coffee, kids chasing pigeons, and travelers stopping every few steps for photos. Around the corners, alleys open onto rolling countryside that looks almost unreal. This is a town made for wandering slowly, tasting everything, and letting the day drift by. Check our guide to the best things to do in Pienza and see how easily it steals the spotlight on any Tuscan trip.

Good to know before visiting Cortona