GemmaIf you’ve ever dreamed of wandering through the sun-drenched streets of Tuscany, Cortona is the town that will make that dream feel tangible. Nestled atop a hill in southern Tuscany, Cortona is a charming town full of medieval architecture, winding alleyways, and breathtaking panoramic views. From my own personal experience, walking through this town is like stepping back in time while still feeling entirely present in the moment. Every street, staircase, and piazza seems designed to capture your attention, whether you’re an avid photographer, a history lover, or simply someone who enjoys a leisurely stroll.
Cortona’s Old Town is compact yet layered with history, art, and culture, and the best way to experience it is on foot. Forget buses or taxis—the magic here is in the winding lanes and quiet corners, the hidden cafes, and the sudden vistas that take your breath away. To help you make the most of your visit, I’ve curated 14 scenic walks in Cortona Old Town. Each walk offers a unique perspective of the town, showcasing both its iconic landmarks and its secret nooks that you truly need to see.
1. Piazza della Repubblica: The Heartbeat of Cortona
Every journey through Cortona should begin at Piazza della Repubblica, the town’s main square. This is where life in Cortona pulses most vibrantly, from bustling markets to quiet evenings with a gelato in hand. Walking here, you’ll notice the mix of Renaissance architecture and rustic charm.
Start your walk by sipping a cappuccino at one of the outdoor cafes. The square is surrounded by historic buildings such as Palazzo Comunale, which houses the town hall. From here, it’s easy to branch out into the side streets, letting your curiosity guide you toward hidden alleyways or panoramic viewpoints.
2. Via Nazionale: Cortona’s Main Artery
From Piazza della Repubblica, head along Via Nazionale, Cortona’s main shopping street. It’s more than just shops; it’s a corridor of history. Along the way, you’ll pass quaint boutiques, local bakeries, and artisan shops selling everything from handmade ceramics to Tuscan olive oil.
Based on my overall experience, this walk is perfect for those who enjoy combining sightseeing with a little retail therapy. Take your time, peek inside the stores, and don’t rush—the charm of Cortona is best experienced at walking pace.
3. The Etruscan Walls Walk
Cortona has a rich history that dates back to the Etruscans, and one of the most fascinating walks takes you along the remnants of the ancient Etruscan walls. These stones have witnessed thousands of years of history, and walking alongside them gives you a tangible sense of the town’s past.
The walk provides occasional glimpses of the valley below, and the contrast between the rugged ancient walls and the colorful rooftops is stunning. Don’t forget your camera—every angle seems to demand a photograph.
4. Fortezza del Girifalco Path
For a more elevated experience, the Fortezza del Girifalco offers panoramic views that are hard to beat. This fortress dates back to the 16th century, and the walk up to it is as rewarding as the destination.
The path winds through quiet streets and small gardens, gradually revealing the town’s rooftops and the rolling Tuscan landscape. From my own personal experience, standing at the fortress at sunset is one of Cortona’s most magical moments. The golden light bathes the town in warmth, and the valley stretches endlessly below you.
5. Via del Teatro Romano: A Walk Through History
Next, explore Via del Teatro Romano, a street that leads to the remains of Cortona’s Roman theater. The walk itself is lined with stone buildings, ivy-covered walls, and a few hidden cafes where you can pause for a snack.
Arriving at the theater, you’ll step into a piece of ancient history. The site is well-preserved and offers a fascinating glimpse into Cortona’s Roman past. Walking here is like connecting two worlds—the bustling town above and the echoes of performances from centuries ago.
6. Camucia Riverside Stroll
Although Cortona Old Town is hilltop, the nearby Camucia area by the river is perfect for a gentle riverside walk. Here, you’ll encounter a mix of locals jogging, couples strolling, and photographers capturing reflections on the water.
This walk offers a refreshing change of pace. The greenery and calm water provide a serene counterpoint to the historic streets, making it an ideal spot for reflection or even a picnic.
7. Via Guelfa and Artisan Workshops
One of the joys of walking Cortona is discovering its artisan culture. Via Guelfa is known for workshops and studios where you can watch craftspeople at work, creating everything from leather goods to hand-painted ceramics.
Take your time here—you might stumble upon a shop where the owner is willing to explain their craft, or even invite you to try your hand at painting a tile. This walk turns shopping into an experience and learning opportunity all at once.
8. San Francesco Church Walk
No visit to Cortona is complete without seeing San Francesco Church. The path leading to it winds through quiet lanes, giving you a sense of the town’s rhythm away from the tourist crowds.
The church itself is a beautiful example of medieval architecture. Walking around the piazza outside, you’ll notice local life unfolding—children playing, neighbors chatting, and the occasional musician filling the air with melody.
9. Piazza Signorelli: Art and Life
Piazza Signorelli is smaller and quieter than Piazza della Repubblica, but it has its own charm. Named after the painter Luca Signorelli, the square is surrounded by art galleries, shops, and cafes.
A walk here feels intimate and personal. From my overall experience, this is where you can truly slow down and observe the subtle details of Cortona—the texture of the cobblestones, the scent of fresh bread, the friendly nods of locals.
10. Santa Margherita Viewpoint Walk
For a scenic overlook that will leave you speechless, head toward Santa Margherita. The walk itself is uphill, but it’s dotted with benches and small gardens where you can pause.
From the viewpoint, the landscape stretches endlessly. Rolling hills, olive groves, and vineyards dominate the horizon, and the town below looks like a painting. This is one of those walks where you just stop and breathe in the beauty around you.
11. Hidden Alleyways of Cortona
Cortona is full of hidden alleyways that feel like secret discoveries. Wander aimlessly through these narrow streets and you’ll stumble upon charming doors, hidden courtyards, and small fountains.
Some alleys are so narrow that you can only walk in single file, adding to the sense of intimacy. These walks are perfect for those who enjoy exploration and surprises, as each corner could reveal a new perspective of the town.
12. Eremo Le Celle Walk: A Spiritual Retreat
If you enjoy combining walking with a touch of spirituality, Eremo Le Celle is a must-see. This small hermitage, founded by St. Francis of Assisi, is accessible via a gentle uphill path.
The surroundings are serene, with cypress trees and panoramic views that feel untouched by time. From my own personal experience, walking here is not just about sightseeing—it’s a moment of quiet reflection amid the beauty of Cortona.
13. Scenic Sunset Walk Around the Town Walls
There’s nothing quite like a sunset walk along Cortona’s town walls. The path offers changing perspectives as the sun dips behind the hills.
You’ll notice the rooftops bathed in golden light and the streets slowly emptying as locals head home. This walk is perfect for those who want to end the day on a peaceful note while capturing some stunning photographs.
14. Via Roma: A Gentle Descent
Finally, finish your exploration with Via Roma, which gently descends toward the lower part of town. Along the way, you’ll pass historic buildings, small gardens, and charming cafes.
The walk offers a sense of closure, connecting the elevated historic center with the areas below. From here, you can catch a bus back, grab a meal at a local trattoria, or simply linger to enjoy one last view of the town.
Tips for Enjoying Your Walks in Cortona
- Wear comfortable shoes: The streets are cobblestone, and some walks are uphill.
- Take your time: Cortona is meant to be savored, not rushed.
- Bring a camera: Almost every corner is Instagram-worthy.
- Stop for food and coffee: Local cafes and trattorias offer some of Tuscany’s best flavors.
- Respect the locals: Cortona is lived-in, so enjoy the town while being mindful of private spaces.
Cortona Old Town offers a mix of history, culture, and breathtaking scenery that can’t be fully captured in a guide alone. The real magic comes from wandering, discovering, and letting the town surprise you. Whether you’re exploring ancient walls, quaint piazzas, or hidden alleyways, these 14 walks will help you experience the town as it was meant to be—slowly, thoughtfully, and with your senses wide open.
From my own personal experience, there’s a kind of joy in Cortona that’s hard to describe but impossible to forget. Every street tells a story, every viewpoint offers a painting, and every corner invites you to linger just a little longer.
Cortona isn’t just a town you visit—it’s a town you feel, explore, and fall in love with.
I’m Gemma, a passionate lifestyle blogger sharing my creative world with you. Gemitaliano.com is my little corner of the internet, glad you’re here.