Cortona’s position in eastern Tuscany makes it one of the best bases for day trips in all of Italy. Within an hour by car, you can reach medieval hill towns, world-famous wine regions, an extraordinary lake, and one of Tuscany’s most beautiful cities. Here’s our guide to the best day trips from Cortona.

Day trips from Cortona — Montepulciano hilltop town viewed across the Tuscan countryside — Photo: Cortona Insider

Montepulciano — 40 Minutes

Montepulciano is the closest of the great Tuscan hill towns — just 40 minutes by car — and one of the most rewarding. Perched on a long narrow ridge with extraordinary views in every direction, it’s home to one of Tuscany’s finest Renaissance piazzas, the Piazza Grande, and to the wine that made it famous: Vino Nobile di Montepulciano, one of Italy’s most celebrated reds.

The town is steep, beautiful, and full of wine cellars (cantine) built into the medieval walls — many open for tasting. The Cantina Contucci, inside the Palazzo Contucci on the main piazza, has been producing Vino Nobile since the 18th century and is one of the finest cellar experiences in Tuscany.

Insider tip: Visit on a weekday morning in spring or autumn. Montepulciano gets crowded in summer — arriving early gives you the town almost to yourself before the coach tours arrive.

Pienza — 50 Minutes

Pienza is one of the most extraordinary places in Tuscany — a Renaissance “ideal city” built in the 1460s by Pope Pius II on a hilltop overlooking the Val d’Orcia. The result is a perfectly proportioned piazza, a cathedral, a papal palace, and streets lined with food shops selling the town’s most famous product: Pecorino di Pienza, some of the finest sheep’s cheese in Italy.

Pienza is small — you can walk the entire historic centre in 20 minutes — but it rewards slow exploration. The views from the city walls over the Val d’Orcia are among the most photographed in Tuscany, and rightly so.

Insider tip: Combine Pienza with Montepulciano in a single day — they’re only 20 minutes apart. Lunch in Pienza, afternoon wine tasting in Montepulciano.

Arezzo — 30 Minutes

Arezzo is the closest city to Cortona — just 30 minutes by car or train — and one of the most underrated in Tuscany. Most visitors skip it in favour of Florence or Siena, which means you’ll often have it largely to yourself.

The highlights are exceptional: the Basilica di San Francesco, home to Piero della Francesca‘s extraordinary fresco cycle The Legend of the True Cross — one of the masterpieces of Italian Renaissance art; the magnificent Piazza Grande, one of the finest medieval squares in Italy; and the Fiera Antiquaria, a famous antiques market held on the first weekend of every month.

Arezzo is also famous for its goldsmiths and jewellers — the city produces more gold jewellery than anywhere else in Europe.

Insider tip: Book tickets for the Piero della Francesca frescoes in advance — access is timed and numbers are limited. It’s worth every effort to see them.

Lake Trasimeno — 30 Minutes

Lake Trasimeno is visible from almost everywhere in Cortona — that shimmer on the southern horizon, just across the Umbrian border. The largest lake in central Italy, it’s one of the region’s most beautiful and least-visited destinations.

The lake is dotted with small towns: Castiglione del Lago, with its medieval fortress jutting into the water, is the most popular; Passignano sul Trasimeno is quieter and more authentic; and the three lake islands — Isola Maggiore, Isola Minore and Isola Polvese — are accessible by ferry and offer extraordinary tranquillity.

In summer, the lake is ideal for swimming, cycling around its shores, or simply sitting by the water with a glass of local wine.

Insider tip: Take the ferry to Isola Maggiore — the smallest inhabited island, with a single village, a lace-making tradition, and the kind of quiet that’s almost impossible to find in summer Tuscany.

Siena — 1 Hour 15 Minutes

Siena is one of the great medieval cities of Europe — and unlike Florence, it has remained largely unchanged since the 14th century. The Piazza del Campo, shaped like a scallop shell and built on a gentle slope, is one of the most beautiful public spaces in the world. The Duomo is extraordinary. The city’s medieval contrade (neighbourhoods) are still fiercely loyal to their traditions.

Siena is larger than the other day trip destinations and deserves a full day. If you can only make one day trip from Cortona, make it Siena.

Insider tip: Climb the Torre del Mangia — the tower overlooking the Piazza del Campo — for the finest view of the city. Go early morning before the queues build.

Assisi — 1 Hour

Assisi is just across the Umbrian border — an hour by car from Cortona — and one of the most spiritually significant places in Italy. The birthplace of St Francis, it sits on the slopes of Monte Subasio with views over the Valle Umbra that are genuinely moving.

The Basilica di San Francesco, built over the tomb of the saint, contains Giotto’s famous fresco cycle — one of the most important works in the history of Western art. The town itself, with its pink-stone streets and medieval atmosphere, is beautiful in every season.

Insider tip: Visit the Eremo delle Carceri — the forest hermitage above Assisi where Francis came to pray — if you want to understand what he was actually looking for. Quieter and more powerful than the basilica.

San Gimignano — 1 Hour 15 Minutes

San Gimignano is famous for its medieval towers — fourteen still standing from an original 72 — and for its gelato (though we maintain that Gelateria Dolce Vita in Cortona does it better). It’s a UNESCO World Heritage Site and one of the most visited towns in Tuscany.

Go early or late — San Gimignano is overwhelmed by day-trippers in summer. The towers are extraordinary. The white wine, Vernaccia di San Gimignano, is excellent. The town is worth seeing despite the crowds.

Insider tip: The best view of the towers is from outside the walls — particularly from the road approaching from the south. Stop before you enter town and take it in.

Quick Reference

Destination	Distance	Best for
Arezzo	30 min	Art, antiques, architecture
Lake Trasimeno	30 min	Swimming, cycling, islands
Montepulciano	40 min	Wine, hilltop views
Pienza	50 min	Cheese, Val d’Orcia views
Assisi	1 hour	Art, spirituality, history
Siena	1h 15 min	Medieval city, full day
San Gimignano	1h 15 min	Towers, wine, views

Insider Tip: Day Trips from Cortona

Cortona is an exceptional base precisely because it sits at the meeting point of Tuscany and Umbria. Most of these destinations are less than an hour away — which means you can explore a different corner of central Italy every day and return to Cortona each evening. That combination of a beautiful home base and extraordinary day trip options is rare even in Italy.