GemmaCortona does not shout for attention. It does not rush you. It simply waits on its hill, quietly confident, knowing that once you arrive, history will do the talking for it. This small Tuscan town feels lived in, layered, and proudly unchanged. Streets twist with purpose, stones sit where they have rested for centuries, and every view feels earned rather than staged.
If you love places where the past feels close enough to touch, Cortona delivers that feeling in full. This is not a place you rush through with a checklist and a camera on autopilot. It invites slow steps, curious pauses, and the kind of wandering that leads you somewhere unexpected.
Below, you will find ten meaningful things to do in Cortona if history excites you. These are not rushed stops or surface-level highlights. These are places and experiences that help you understand how this town became what it is today, and why it still feels so deeply rooted.
1. Walk the Ancient Etruscan Walls
Before Cortona was Roman, before it was medieval, before Tuscany even meant Tuscany, this hill belonged to the Etruscans. Their presence still defines the town, and nowhere is that clearer than in the ancient stone walls that wrap around Cortona like a protective memory.
As you walk alongside these massive blocks of stone, it becomes clear that this was not casual construction. The stones are enormous, fitted together with a confidence that suggests skill passed down through generations. Some sections date back more than two thousand years, yet they still stand without complaint.
This walk is quiet, especially in the early morning or late afternoon. You may hear footsteps echo briefly, then disappear. That silence gives the walls space to speak in their own way. You start to imagine guards watching the valley below, traders approaching from a distance, and entire lives unfolding under this same skyline.
History here is not locked behind glass. You move beside it, touch it, and walk at its pace.
2. Visit the Museo dell’Accademia Etrusca
If the walls spark your curiosity, the Museo dell’Accademia Etrusca answers it.
Located in the Palazzo Casali, this museum does an excellent job of explaining who the Etruscans were and why they mattered. It is not overwhelming, and it does not assume you already know everything. Instead, it guides you gently through centuries of local history.
One of the most impressive pieces is the bronze chandelier, detailed and symbolic, offering insight into Etruscan beliefs and craftsmanship. You will also see funerary urns, inscriptions, coins, and objects taken from nearby tombs.
What makes this museum special is how closely it connects to the town itself. These items did not come from far away. They came from under the same ground you are walking on.
You leave with context. Suddenly, Cortona makes more sense.
3. Explore Piazza della Repubblica
Every historic town has a heart, and in Cortona, it beats in Piazza della Repubblica.
The square feels honest. Locals pass through it daily. Conversations happen naturally. There is no pressure to perform for visitors, which makes it even better.
The Palazzo Comunale dominates the square with its clock tower and wide staircase. This building has governed the town for centuries, adapting as power shifted from one era to another.
Sit on the steps for a moment. Watch the rhythm of daily life. This is how history survives — not through preservation alone, but through continued use.
At certain times of day, the light settles gently on the stone. It is the kind of moment that makes you stop talking mid-sentence.
4. Step Inside the Cathedral of Santa Maria Assunta
From the outside, the cathedral appears restrained. Inside, it surprises you.
The Cathedral of Santa Maria Assunta holds layers of time within its walls. The structure you see today reflects Renaissance influence, but it stands on much older religious ground.
Paintings line the interior, each with its own story, each reflecting the beliefs and artistic direction of its time. The atmosphere remains calm, even when visitors come and go.
This is not a place of spectacle. It is a place of continuity.
You sense that prayers have been spoken here for generations, whispered in moments of hope, fear, gratitude, and doubt. That emotional history lingers quietly in the air.
5. Wander Through the Medieval Streets
Cortona is best understood on foot, without direction.
Its streets curve with intention, shaped by centuries of defense, trade, and daily living. Some paths narrow suddenly, then open into small squares that feel like secrets.
As you walk, look closely. Stone door frames show wear from hands long gone. Small religious images are built directly into walls. Old iron rings remain where animals were once tied.
This is where history stops being something you read about and becomes something you notice.
At some point, you will get slightly lost. That is part of the experience. Cortona rewards wandering more than planning.
6. Visit the Church of San Francesco
This church sits quietly, often overlooked, yet it carries deep spiritual and historical weight.
Dedicated to Saint Francis, the building reflects simplicity and humility. Inside, the atmosphere feels grounded and sincere. Frescoes and artwork speak softly rather than demand attention.
Saint Francis himself passed through Cortona, and his influence shaped much of the town’s spiritual identity. Standing inside this church helps you understand how faith once guided everyday life.
There is no rush here. Take a seat. Let the silence do its work.
7. Discover the Diocesan Museum
Tucked near the cathedral, the Diocesan Museum holds an impressive collection of sacred art.
Here, you will find works by Luca Signorelli, one of the most important painters of the Renaissance. His dramatic use of form and emotion bridges the gap between medieval tradition and emerging modern expression.
The museum is compact but rich. Each room feels purposeful. You can take your time without feeling overwhelmed.
This visit deepens your understanding of how religion, art, and local identity developed side by side.
8. Climb to the Fortress of Girifalco
If you want perspective, both literal and historical, climb to the Fortress of Girifalco.
This stronghold stands at the highest point of Cortona. Over the centuries, it has been expanded, reinforced, and reshaped to meet changing military needs.
From the top, the Val di Chiana stretches out below you. It becomes easy to understand why this position mattered so much. Control the hill, and you control the view, the movement, and the warning signs of danger.
The walk up is worth every step. The view is wide, quiet, and unforgettable.
9. Learn About Saint Margaret of Cortona
Saint Margaret is one of the most important figures in the town’s history.
Her life story is deeply human, marked by struggle, loss, and transformation. She lived in Cortona during the 13th century and became known for her compassion and service.
The Basilica of Saint Margaret sits above the town and offers insight into her legacy. Inside, her story unfolds through art and devotion.
This is not history told through kings or battles. It is history told through resilience.
Based on my overall experience walking through this site, it leaves a stronger emotional impression than many grander monuments.
10. Take Time to Simply Observe
The final thing to do in Cortona requires no ticket and no location.
Slow down.
Sit on a stone bench. Watch the way locals greet each other. Notice how the town changes tone as the day moves on. Listen to footsteps echo in narrow streets at night.
History does not only live in buildings. It lives in rhythm, habit, and continuity.
Cortona has survived because it never tried to reinvent itself loudly. It adjusted quietly, generation after generation.
Why Cortona Stays With You
Some places impress you. Others stay with you.
Cortona belongs to the second group. It does not rely on spectacle or exaggeration. Its power comes from authenticity.
You do not need to imagine the past here. It is already present, layered gently into daily life.
If you love history that feels lived rather than staged, this town offers something rare. You leave with more than photos. You leave with understanding.
And somehow, even after you go, Cortona continues to feel close — like a story you can return to whenever you need to remember how deeply time can shape a place.
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.