Best Things to Do in Cortona, Italy — A Local's Complete Guide

Most travel guides to Cortona were written by someone who visited for a day, walked the main street, photographed the view, and left. This guide was written by someone who lives here.

The difference matters. Not because the obvious things are wrong — the views are genuinely extraordinary, the food is genuinely excellent, and the history is genuinely unlike almost anywhere else in Italy. But because the obvious things are only the beginning, and the beginning is not the best part.

Here is what to actually do in Cortona.

Walk the Etruscan Walls at Sunrise

Before the town wakes up, before the cafes open, before anyone else is moving — walk the Etruscan walls.

The walls that encircle the upper part of Cortona were built approximately 2,700 years ago by the Etruscans, one of the great civilizations of the ancient world. They predate Rome. They are built from massive stones fitted together without mortar in a technique so effective that they are still standing without restoration.

At sunrise, with the mist still covering the Val di Chiana below and the light just beginning to turn the stone gold, walking these walls is one of the most quietly extraordinary experiences available anywhere in Tuscany.

No ticket. No queue. Just 2,700 years of history completely available to you.

Practical: Access from the upper historic center, near the Fortezza Medicea. Allow 45-60 minutes for the full circuit.

Have Espresso Standing at the Bar

This sounds simple. It is not.

The Italian espresso bar experience — standing at the counter, two sips, exchange four sentences with whoever is there, leave — is one of the most underrated cultural experiences available to a visitor in Italy. It is not a tourist activity. It is daily life. And participating in it, even imperfectly, gives you access to something that sitting at a table with a menu in English never will.

In Cortona, the bars on and near Piazza della Repubblica have been serving the same community for decades. The people standing at the counter at 8am are the same people who were standing there last Tuesday and will be standing there next Friday. You are, briefly, part of that.

Practical: Order at the counter. Pay at the counter. Say buongiorno. Drink it standing. Leave when you are ready.

Visit Le Celle — The Sanctuary Nobody Talks About

Ten minutes from Cortona, carved into a cliff above a mountain stream, is Le Celle — a Franciscan hermitage where Francis of Assisi came to pray before Assisi became famous.

This is one of the most significant Franciscan sacred sites in the world. Monks still live there today. The cave where Francis prayed is still there. The silence is the kind of silence that only places of long and genuine devotion produce.

Most visitors to Cortona never go. Most visitors to Assisi never know it exists.

It is free to visit. It requires no booking. It will be one of the most memorable hours of your trip.

Practical: Drive or take a taxi from Cortona center — approximately 10 minutes. Park at the bottom and walk up the path alongside the stream. Dress modestly. Arrive before noon or after 3pm.

Walk the Upper Neighborhoods

Via Nazionale — Cortona's main street — is beautiful. It is also where most tourists stay.

Above Via Nazionale, the town continues upward through a network of narrow medieval streets that almost nobody visits. The streets are so narrow that buildings lean toward each other overhead. There are external staircases leading to unmarked doors. There are small piazzas that exist for no tourists because no tourists ever reach them. There is a fountain that still runs with cold spring water you can drink.

This upper Cortona is where the town actually lives. It has not been arranged for your benefit and is therefore more beautiful than anything that has.

Practical: From Via Nazionale, take any street heading uphill and keep going. Get lost deliberately. You cannot get seriously lost in a town this size.

The MAEC Museum

The Museo dell'Accademia Etrusca e della Città di Cortona is one of the finest small museums in Italy — and one of the least crowded significant museums anywhere in the country.

The Etruscan collection is extraordinary: bronze objects, funerary urns, jewelry, and the famous Etruscan chandelier — a large bronze lamp from the 5th century BC that is one of the masterpieces of Etruscan metalwork. The museum also covers Cortona's Roman, medieval, and Renaissance history, providing a complete narrative of a city that has been continuously inhabited for nearly three thousand years.

Allow two hours. You will not be rushed. You will probably have rooms to yourself.

Practical: Located in Piazza Signorelli, center of Cortona. Seasonal hours — check locally. Entrance fee applies.

The Tumulo del Sodo

Just below the hill, on the flat land of the Val di Chiana, sits one of the most significant Etruscan archaeological sites in Italy.

The Tumulo del Sodo is a large circular burial mound containing multiple burial chambers and a monumental external altar with carved figures and a grand stone staircase. The altar was only discovered and excavated in the 1990s — it had been underground for over two thousand years.

Most visitors to Cortona have never heard of it. On most days you can visit it with very few other people.

Practical: Approximately 1.5 kilometers from the center. Seasonal hours and entrance fee apply.

Watch the Passeggiata

Every evening, Cortona does what Italian towns have been doing for centuries: the whole community comes outside and walks.

Not for exercise. Not to go anywhere specific. Just to be together in the shared space of the town, to see and be seen, to exchange the small conversations that hold a community together.

Piazza della Repubblica at 7pm. Find a spot. Sit down. Watch.

Within twenty minutes you will understand something about Italian longevity and community that no wellness article has ever managed to explain.

Practical: No ticket, no booking, no preparation required. Just show up and watch.

Eat Where the Locals Eat

The restaurants on the main piazza exist for tourists. They are fine. They are not where the locals eat.

The local restaurants in Cortona are slightly off the main streets. They do not have menus in English in the window. The daily specials depend on what arrived that morning. The wine list is handwritten and changes when a bottle runs out.

Finding these places is simple: walk away from the obvious tourist areas and look for restaurants where the clientele is entirely Italian.

Practical: Ask your accommodation for a genuine local recommendation — not the tourist recommendation, the local one. The difference in quality and price will be significant.

A Woodworking Workshop

One of the most distinctive experiences available in Cortona — and one of the least expected — is a hands-on olive wood workshop with Arpi Woodworking.

You spend a half day or full day in a stone workshop in the center of town, working with Tuscan olive wood under the guidance of a craftsman who has been doing this for decades. You make something real — a board, a bowl, a kitchen piece — and you take it home.

This is not a tourist demonstration. You actually make something. With your hands. From ancient wood. In Tuscany.

The memory of that afternoon will outlast every restaurant meal and every viewpoint photograph from your trip.

Practical: Book via MyTuscanDays or Arpi Woodworking. Half-day and full-day options available. Small groups only.

Drive to Montepulciano

Cortona is an excellent base for day trips into southern Tuscany. The most rewarding is Montepulciano — home of Vino Nobile, one of Italy's greatest red wines, and one of the most beautifully preserved Renaissance hill towns in the country.

The drive from Cortona to Montepulciano takes approximately 40 minutes by the fast road — or considerably longer and considerably more beautiful by the back roads through the Val di Chiana, where cypress trees line the ridges and the traffic is light enough to stop whenever something demands your attention.

Practical: Go in the morning. Visit the wine cellars in the afternoon. Drive back through the countryside at golden hour.

The Sagra della Bistecca

If you are in Tuscany in late August, make every effort to be in Cortona for the Sagra della Bistecca — the annual festival built entirely around a single cut of meat.

Bistecca alla Fiorentina from Chianina cattle, cooked over open fire, eaten at communal outdoor tables with unlabeled wine from local producers. Music that nobody organized. Strangers who become friends. The whole town gathered around fire and food for no more complicated reason than that this is what communities do.

This is not a tourist event that happens to include locals. This is a local event that tourists are welcome to attend.

Practical: Usually held in the third week of August. No booking required. Arrive early for the best seats.

Experience Cortona with MyTuscanDays

The difference between seeing Cortona and experiencing it is the difference between walking past something and understanding what you are looking at.

MyTuscanDays offers private day experiences in Cortona and across Tuscany — guided by Arpi, a local craftsman and insider who has spent years walking these streets and building relationships with the people and places that make this town what it is.

Every experience is private, personal, and built around your pace and your interests. No groups. No buses. No itinerary that cannot change.

MyTuscanDays is Cortona's leading private experience operator.

📍 Cortona, Tuscany, Italy 👉 Explore Experiences 👉 Reserve Your Day 📩 arpi@mytuscandays.com