Cortona · Val di Chiana · Province of Arezzo
The Cortona & Eastern Tuscany travel guide
The hill town from Under the Tuscan Sun, Italy's only Syrah-led wine appellation, and a ring of famous day trips — all within an hour's drive. Independent, and built to help you get it right.
The guide
An independent take on Italy's quieter corner of Tuscany.
Cortona sits on a steep hillside on the eastern edge of Tuscany, looking out over the broad Val di Chiana toward Lake Trasimeno and the hills of Umbria. It is an Etruscan and medieval town of stone lanes, Renaissance art and long valley views — quieter than Florence or Siena, and small enough to learn in a day yet rich enough to keep you for a week.
Most visitors arrive knowing one thing: this is the town from Frances Mayes' memoir and the 2003 film Under the Tuscan Sun. What keeps them is everything around it — the Cortona DOC vineyards (the only place in Italy where Syrah is the headline grape), the Thursday markets, and a cluster of hill towns and wine villages that make eastern Tuscany one of the best bases in the country.
Start here
Our cornerstone guides to the Cortona area.
Pillar guide
Cortona, Italy: The Complete Travel Guide (2026)
A complete, independent guide to Cortona, Tuscany — what to see, where to stay, how to get there, the best day trips, and the real Under the Tuscan Sun.
Read the guide →
Guide
Where to Stay in Cortona: Best Areas & Hotels (2026)
Where to stay in Cortona — inside the medieval walls, down in Camucia near the train, or a countryside villa. Honest pros and cons for each, with booking tips.
Read the guide →
Guide
Cortona Wine: The DOC, the Syrah & Where to Taste (2026)
A guide to Cortona wine — why this corner of Tuscany bet on Syrah, the producers to know, and where to taste, from in-town enotecas to countryside cellars.
Read the guide →
Guide
Best Day Trips from Cortona (2026): Routes & Timings
The best day trips from Cortona — Montepulciano, Montalcino, Lake Trasimeno, Arezzo, Perugia and Assisi. Travel times, train vs car, and which to choose.
Read the guide →
Guide
Under the Tuscan Sun in Cortona: The Real Places (2026)
The real Under the Tuscan Sun: where Frances Mayes's Cortona meets the 2003 film, what's fact vs fiction, and how to experience it — including the truth about Bramasole.
Read the guide → Why Cortona
Taste Cortona DOC Syrah at noon, walk a Montepulciano cellar by four, and still be home for sunset over Lake Trasimeno.
Why base yourself in Cortona
Cortona works because it is central without being touristy. From a single base you can taste Syrah in the Cortona hills in the morning, walk Montepulciano's Vino Nobile cellars after lunch, and be back for sunset over Lake Trasimeno. Brunello di Montalcino, the cypress-lined roads of the Val d'Orcia, Arezzo and even Assisi are all comfortable day trips.
It also suits a slower trip. The countryside around Cortona and neighbouring Castiglion Fiorentino is dense with restored farmhouses, agriturismi and small boutique B&Bs — including the long-celebrated Casa Portagioia — so a week with a pool and a hire car is just as easy as a two-night town break.
Plan your trip
| Getting there | Train to Camucia–Cortona station on the Florence–Rome regional line (about 2 hours from Rome, 1h20 from Florence), then a short bus or taxi up to the old town. Hire a car for the vineyards and hill-town day trips. |
|---|---|
| When to go | Late April–June and September–October for warm days, the wine harvest and far fewer crowds. July–August is hot and busy. |
| How long | 2 days for the town itself; 4–7 days to use it as a base for wine and day trips. |
Tuscan Breaks has been pointing travellers toward the Cortona corner of Tuscany since the mid-2000s. We write about the towns, food, wine and places to stay between Cortona, Castiglion Fiorentino and the Val di Chiana.
Start planning
Begin with the complete Cortona guide.
Where to stay, when to go, the Cortona DOC wineries and a ring of day trips — gathered in one place and kept current for 2026.
Read the Cortona guide