Things to do in Cortona for self travelers
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This in-app audio tour unfolds the rich tapestry of Cortona, a Tuscan town drenched in history and tradition. Ideal for travelers with a thirst for culture, the tour invites participants on a captivating journey through time. Its focus lies in tracing the legacy of ancient civilizations and the echoes of the Etruscan roots that Cortona is so proud of. Beginning at the vibrant heartbeat of the town, Piazza della Repubblica, history enthusiasts will embark on an expeditious adventure that winds through the cobblestone streets, dipping into the layers of past epochs while being immersed in the ambiance that inspired 'Under the Tuscan Sun'. The tour's route guides the listener from the central piazza, past Etruscan walls, through serene spiritual sites like the Basilica of Santa Margherita, and up to the strategic Fortress of Girifalco. Along the way, enriching tales of Saint Margaret's virtuous life and the art of Luca da Cortona unravel. The pathway concludes back in the town center, where one's imagination will have been painted with images of Cortona through the ages. This tour is a solo expedition, but with storytelling that conjures the sensation of walking through history with old friends. Travelers will not only discover the architectural marvels and sacred spaces that punctuate Cortona but will also be treated to stories that breathe life into stone walls and silent bell towers. From following in the footsteps of saints and artists to the flavors of traditional Tuscan cuisine, this tour ensures an experience that lingers much like the town's timeless charm.
About Cortona
The best walking tours to do in Cortona are:
The best tours to do in Cortona with kids are:
The must-see attractions in Cortona for a first visit are:
The best tours in Cortona are:
The best indoor tours in Cortona for rainy days are:
Insider tips for visiting Cortona
Kseniya Strukova is a local guide who has been publishing tours since 2024 for your discovery of hidden gems and local specialities of Cortona on their personal guide page (view profile). Explore their expert tips planning trip to Cortona.
When I visit Cortona for shopping, I always start along Via Nazionale and the smaller lanes branching toward Piazza della Repubblica. This part of Cortona has the best mix of family-run boutiques, leather goods, local linens, and food shops where I pick up pecorino, truffle products, and Tuscan wine. I also like wandering Via Guelfa and Via Roma, where artisan jewelry and ceramics feel much more local than souvenir-heavy. If you visit Cortona on a market day, the atmosphere is even better. In my travel guide Cortona notes, I always say this is one of the most enjoyable things to do in Cortona because the town still feels genuinely lived-in.
When I want quieter attractions in Cortona, I slip into the little streets behind Piazza della Repubblica and walk up to the Eremo Le Celle, a peaceful Franciscan hermitage tucked into the woods just outside Cortona. I also love the Church of San Niccolò for its early frescoes and the olive groves around it, especially late in the afternoon. Locals know the public garden at Parterre is one of the best places to pause and look over the Valdichiana. If you’re deciding what to see in Cortona beyond the main squares, these spots feel personal and unhurried. Even people browsing tours in Cortona often miss them.
In my travel guide Cortona notes, I usually recommend at least two nights. Cortona reveals itself slowly: one day for the historic center, San Francesco, and the views from Parterre, then another for Le Celle, the MAEC museum, and a long lunch or wine tasting nearby. When I visit Cortona, I like having a third day to explore the quiet lanes early in the morning, when locals are opening shops and the town feels most authentic. If you only visit Cortona for a few hours, you’ll see the highlights, but many of the best things to do in Cortona are the slower, in-between moments.
For me, one of the best things to do in Cortona alone is to walk from the historic center out to Eremo Le Celle. It’s an easy way to experience Cortona beyond the busy piazzas, and I find the wooded path and stone hermitage especially rewarding when traveling solo. I usually stop first at Parterre for the valley view, then wander back through Cortona to San Niccolò and the quieter lanes near Via Guelfa. If you’re deciding what to see in Cortona, this mix of peaceful walking and small-scale attractions in Cortona feels very comfortable on your own. Even people comparing tours in Cortona often overlook it.
If you visit Cortona for local events, I’d time it for the Giostra dell’Archidado in June. Cortona fills with flag throwers, archers, and residents in medieval dress, but what I love most is how the smaller streets and taverns get involved, not just the main square. I also enjoy the annual antiques fair, where Cortona’s old-town streets feel especially lively and local collectors arrive early. In my travel guide Cortona notes, I always mention Christmas too, when the town is quieter and more intimate, with lights and seasonal markets. For me, these are some of the most memorable things to do in Cortona.
When I want to go beyond the main attractions in Cortona, I usually head into the hills and small villages around it. One of my favorite outings from Cortona is up to the Fortezza del Girifalco for wide views, then down to Le Celle, which feels wonderfully hidden among the trees. I also recommend driving or biking toward the Val di Chiana farms, where you can stop for olive oil, pecorino, and quiet vineyard lunches. If you’re deciding what to see in Cortona and nearby, Lake Trasimeno is an easy half-day trip that locals actually do. Even visitors looking at tours in Cortona often miss how good the countryside is.
In my travel guide Cortona notes, I usually recommend late April to June or September to early October. That’s when I most enjoy Cortona: the light is soft, the hills are green or golden, and you can still find a quiet bench at Parterre or an unhurried walk to Le Celle. Summer brings more energy, but the steep streets of Cortona can feel hot by midday. If you visit Cortona in autumn, the harvest season adds a special rhythm, with new olive oil, local wine, and fewer crowds. For me, that balance makes it one of the best times for the slower things to do in Cortona.
On a first trip, I recommend keeping Cortona simple and walkable. I usually begin in Piazza della Repubblica, then wander uphill through the smaller lanes to Santa Margherita and the Girifalco fortress for the best views over the Valdichiana. After that, I like to come back down through Cortona to San Francesco or the MAEC museum, depending on whether I’m in the mood for art or archaeology. These are some of the essential things to do in Cortona, but I’d also leave time for an espresso on Via Nazionale and a quiet detour to Le Celle. That mix gives you a real feel for what to see in Cortona beyond standard tours in Cortona.