For a first day trip from Cortona, choose Arezzo without a car, Lake Trasimeno for a slower day, or Montepulciano and Pienza for a drive through southern Tuscany. Perugia and Assisi are good choices for a full day in Umbria; Montalcino suits a dedicated wine-country outing.
This guide is part of our complete Cortona travel guide. Your starting point matters: Cortona’s historic centre is on a hill, while Camucia-Cortona and Terontola-Cortona railway stations are below it. A train journey time is not the same as the time from your hotel to the destination.
Day trips from Cortona at a glance
These are approximate one-way driving allowances, not live journey estimates. Add parking, walking and stops; check the route from your actual accommodation before departure.
| Destination | Best for | Approximate drive | Without a car? |
|---|---|---|---|
| Lake Trasimeno | Lakeside lunch and a slower pace | 30–45 min, depending on the town | Train to Passignano; check island ferries separately |
| Arezzo | Art and a compact historic centre | 40–50 min | A strong rail choice from Camucia-Cortona |
| Montepulciano | Vino Nobile and hill-town streets | 45–60 min | A car or organised excursion is more practical |
| Perugia | Umbrian art and city life | 50–70 min | Rail via Terontola; allow time to reach the upper town |
| Assisi | Basilica of St Francis | 60–80 min | Rail, then a local connection to the historic centre |
| Montalcino | A dedicated Brunello day | 75–95 min | A car or driver makes the day simpler |
| Pienza & Val d’Orcia | Pecorino and countryside views | 60–75 min to Pienza | Best by car; rural stops add travel time |
Which trip should you choose?
- One free day, no car: start with Arezzo. Keep Perugia or Assisi for a day when the rail connections work well.
- Half a day: choose one Lake Trasimeno town, rather than trying to circle the whole lake and visit an island.
- One day with a car: combine Montepulciano and Pienza, leaving time for lunch and the uphill streets.
- Wine as the main event: choose Montepulciano or Montalcino and reserve tastings. Use a driver if everyone wants to taste.
- Following Under the Tuscan Sun: combine Cortona with a separate Montepulciano day; use our filming locations map and walk.
Before taking the train
Plan three parts of each journey: Cortona to the station, the train, and the station to your destination. Check the last connection back as well as the outward trip. Do not assume a taxi will be waiting for a late return.
Search Trenitalia using the actual station names Camucia-Cortona and Terontola-Cortona, then compare the whole journey. In Umbria, the official transport guide links to buses, local mobility and Lake Trasimeno ferries; it also describes the Assisi Link train-and-bus connection. Ferry services vary by season, so confirm both legs before committing to an island visit.
If most of your days will be by rail, compare staying in Camucia with staying inside Cortona’s walls before booking.
Best by train
If you’re carless and basing yourself inside the walls, these are the easy wins.
Arezzo
Arezzo is a straightforward choice by rail; check the service from your chosen station for the day you travel. Its treasure is Piero della Francesca’s Legend of the True Cross fresco cycle in the Basilica of San Francesco — one of the masterpieces of the early Renaissance (book ahead). Around the first Sunday of the month and the preceding Saturday the whole centre fills with Italy’s most famous antiques fair. Arezzo also starred in Roberto Benigni’s Life Is Beautiful.
Lake Trasimeno
Just across the border in Umbria, Lake Trasimeno is a 30-minute hop. Take the train to Passignano sul Trasimeno for a lakeside lunch and ferries out to Isola Maggiore, or drive around to Castiglione del Lago on its little promontory. In summer it’s a swimming-and-beach day; the rest of the year it’s a gentle, scenic one.
Perugia & Assisi
Umbria’s capital, Perugia, offers medieval streets, a chocolate tradition and art. Check trains via Terontola and the onward connection from the station to the upper town. Assisi is another full-day choice: its railway station is outside the hilltop centre, so include the bus or taxi connection in your plan. Give each town its own day if you want time for museums or churches rather than a rushed stop in both.
Best by car (the wine country)
Southern Tuscany’s wine towns are gloriously scenic and frustratingly ill-served by trains. Do these by car — or book a tour and let someone else drive and pour.
Montepulciano
About an hour southwest, Montepulciano is a steep, handsome Renaissance town famous for Vino Nobile di Montepulciano, one of Tuscany’s classic Sangiovese-based reds. Cellars burrow under the old palazzi right in the centre, so you can taste without leaving town. (Film fans: parts of Twilight: New Moon were shot here, standing in for Volterra.)
Montalcino
Farther west, Montalcino is the home of Brunello, arguably Italy’s most prestigious red wine. The hilltop fortress, the long views, and the chance to taste Brunello at its source make it a bucket-list stop for wine lovers — pair it with the local guide to Cortona’s own Syrah for a complete Tuscan-red education.
Pienza & the Val d’Orcia
The Val d’Orcia is the Tuscany of postcards and screen-savers: rolling hills, solitary cypresses, golden light. Pienza, a perfect little Renaissance “ideal city,” is the place to base a drive through it — and to buy the celebrated local pecorino di Pienza cheese.
How to plan it
A simple rule of thumb:
- Day-trip by train for Arezzo, Perugia, Assisi and Passignano, checking the local connections as well as the railway timetable.
- Day-trip by car or tour for Montepulciano, Montalcino and the Val d’Orcia.
- Going further? Florence and Rome can work as long rail day trips, depending on the service. Compare actual departures, arrival stations and return times before booking timed attractions. For a relaxed first visit, the nearer towns make better use of your day.
If you’re touring the wine country and Val d’Orcia at your own pace, it’s worth basing yourself at a countryside villa with parking rather than inside the walls. And whatever you do, leave at least one full day for Cortona itself — it more than holds its own against any of these.
A three-day plan using Cortona as your base
Day one: Cortona. Explore the squares and use our film-location walk, then leave the afternoon for the town’s museums or viewpoints.
Day two: Arezzo by train, or Montepulciano and Pienza by car. Pick the option that matches your transport. Avoid adding Montalcino to the same driving day if you want time for a tasting and a proper lunch.
Day three: Lake Trasimeno. Choose a lakeside town; add a ferry only if the seasonal timetable leaves enough time for the return. Swap the lake for Perugia or Assisi if art and churches matter more to you than waterside time.
Frequently asked questions
What are the best day trips from Cortona?
The standouts are Montepulciano and Montalcino for wine, Lake Trasimeno for the lakeside and islands, Arezzo for Piero della Francesca's frescoes and its antiques market, and Perugia and Assisi just across the border in Umbria. Choose one main destination per day; Montalcino and some rail journeys take longer than an hour.
Can you do day trips from Cortona by train?
Yes, for some. Arezzo, Perugia and Lake Trasimeno (Passignano) are reachable by train from the Camucia-Cortona or Terontola-Cortona stations, as are Florence and Rome. The wine towns — Montepulciano, Montalcino, Pienza — are awkward without a car, so do those by car or on a guided tour.
Is Cortona a good base for exploring Tuscany and Umbria?
It's one of the best. Cortona has access to the Florence–Rome railway through stations below the hill town and is close to the Umbrian border, so you can reach the wine country of southern Tuscany, the hill towns of Umbria, and the art cities of Arezzo and Perugia — all as day trips — without changing hotels.
How far is Lake Trasimeno from Cortona?
Very close — about 30 minutes by car, or a short train ride to Passignano sul Trasimeno. The lake is just over the regional border in Umbria and makes an easy half-day or full-day trip, with lakeside towns, ferries to the islands, and beaches in summer.