Cortona for First-Timers — Everything You Need to Know
Cortona for first-timers can feel overwhelming at first — where to start, what to see, how long to stay. This guide answers all of it. You’ve made an excellent choice. This small hilltop town in eastern Tuscany is one of Italy’s most rewarding destinations — not because it has the most famous landmarks, but because it has something rarer: genuine character. Here’s everything you need to know before you arrive.
This guide is written specifically for Cortona first-timers — everything you need in one place.
What Kind of Place Is Cortona?
Cortona is a medieval hilltop town of around 22,000 people in the province of Arezzo, sitting at 600 metres above the Val di Chiana. It’s not a theme park version of Tuscany — it’s an actual working town, with residents who have been here for generations, a market on Saturdays, schools, bars where the locals argue about football, and streets that have looked roughly the same for five hundred years.
It became internationally known through Frances Mayes’ memoir Under the Tuscan Sun, but don’t let that define your expectations. Cortona is older, stranger, and more interesting than any book can capture.
How to Get There
Cortona is not directly on a major rail line, but it’s easy to reach. The nearest train station is Camucia-Cortona, about 5 km from the historic centre, on the Florence–Rome line. From there, a local bus or taxi takes you up the hill in minutes.
By car, exit the A1 autostrada at Valdichiana and follow signs for Cortona. The drive from Florence takes about 1.5 hours; from Rome, around 2.5 hours.
For a full guide to getting here, see our How to Get to Cortona guide.
Insider tip: If you’re arriving by car, park at Piazzale del Mercato just outside the historic walls. Don’t attempt to drive inside — most streets are restricted to residents.
Where to Start
Begin at Piazza della Repubblica — the main square, dominated by the 13th-century Palazzo Comunale with its distinctive external staircase. This is the heart of Cortona, and everything radiates from here.
From the piazza, head up Via Nazionale (known locally as “Rugapiana” — the flat street, and the only one in town). At the top, you’ll reach Piazza Signorelli, home to the MAEC Museum, the Teatro Signorelli, and some of the town’s best cafés.
Then start climbing. Cortona rewards those who go uphill — the higher you get, the better the views and the quieter the streets.
What to See and Do
MAEC Museum — Cortona’s most important museum, housing one of the finest Etruscan collections in Italy. Allow 90 minutes. Don’t miss the Etruscan bronze chandelier.
Diocesan Museum — A small but exceptional collection of religious art, including a Fra Angelico Annunciation that alone is worth the entrance fee.
Fortezza del Girifalco — The Medici fortress at the top of the town. Steep climb, extraordinary views. Go at sunset.
Eremo Le Celle — A Franciscan hermitage founded by St Francis of Assisi, tucked into a wooded ravine 3 km from town. One of the most serene spots in Tuscany.
Via Janelli — One of the oldest streets in Cortona, with medieval overhanging houses (sporti) that are among the best-preserved in Italy. Easy to miss, impossible to forget.
For a full guide, see our Things to Do in Cortona guide.
Where to Eat and Drink
Cortona has an outstanding food scene for a town of its size. A few essentials for first-timers:
Morning: Caffè Vittoria on Piazza Signorelli — cappuccino and cornetto at the bar, the Italian way.
Lunch: La Dispensa del Preludio on Via Guelfa — rustic Tuscan food, km0 ingredients, excellent value.
Dinner: Ristorante La Loggetta — classic Tuscan cuisine in a 13th-century building with a terrace overlooking Piazza della Repubblica. Book ahead.
Gelato: Gelateria Dolce Vita on Via Nazionale — the best gelato in Cortona. Possibly the best in Tuscany.
Pizza: Caffè del Torreone, 5 minutes from the centre — the best pizza in Tuscany, full stop.
Where to Stay
For a first visit, stay inside the historic walls if you can. Hotel San Michele — in the 15th-century Baldelli Palace, steps from Piazza della Repubblica — is our top pick. For alternatives, see our Where to Stay in Cortona guide.
When to Go
The best time for a first visit is late April, May, or September — warm, manageable crowds, and Cortona at its most beautiful. Summer is busy and hot but festive. Winter is quiet and authentic.
For a full seasonal breakdown, see our When to Visit Cortona guide.
Essential Tips for Cortona First-Timers
Here are the essential tips every Cortona first-timer needs to know before arriving.
Wear comfortable shoes. Cortona is built on a steep hill. Every street is either uphill or downhill. Beautiful, but unforgiving on unsuitable footwear.
Arrive early or stay late. In summer, the town fills with day-trippers between 10am and 6pm. The best Cortona experience happens outside those hours.
Allow more time than you think. Most visitors plan a half day and wish they’d stayed longer. A full day is the minimum; an overnight stay is strongly recommended.
Get off the main street. Via Nazionale is lovely, but the real Cortona is in the side streets, the upper quarters, the quiet piazzas that most visitors never find.
Learn two words of Italian. “Permesso” (excuse me) and “Grazie” (thank you) will open more doors in Cortona than any guidebook.
Insider tip: The single best thing you can do on a first visit is walk uphill until you find a view, sit down, and do nothing for twenty minutes. Cortona is not a town to be consumed efficiently. It’s a town to be felt slowly.
Quick Reference for First-Timers
| Getting here | Train to Camucia-Cortona, then bus or taxi |
| Parking | Piazzale del Mercato, outside the walls |
| Start here | Piazza della Repubblica |
| Must-see | MAEC Museum, Fortezza, Via Janelli |
| Best restaurant | La Loggetta (book ahead) |
| Best gelato | Dolce Vita, Via Nazionale |
| Best time to visit | May or September |
| How long to stay | Minimum one full day; overnight recommended |
