Castiglion Fiorentino & Cortona: A Tuscan Day Trip by Train from Florence
- realtravelguides
- Sep 24
- 2 min read
Two Tuscan hill towns, one train ride: Castiglion Fiorentino and Cortona make the perfect day trip from Florence. With medieval streets, Renaissance squares, and sweeping views of the Val di Chiana, these towns offer a quieter taste of Tuscany.
Why Go?
Both towns are less crowded than Florence or Siena, yet rich with history and charm. It’s Tuscany at its most authentic, and easy to reach by train.
A bit of History
Castiglion Fiorentino traces its roots to the Etruscans and later flourished as a medieval fortress town. Cortona, even older, was a powerful Etruscan city-state and later a Renaissance hub.
What to Expect
Narrow medieval alleys and steep climbs.
Stunning views of the Val di Chiana and Lake Trasimeno.
Authentic trattorias serving Tuscan staples.
5 Things to Do and See
Visit Castiglion Fiorentino’s Cassero Fortress, with panoramic views.
Explore the Archaeological Museum showcasing Etruscan finds.
In Cortona, admire Piazza della Repubblica and its Renaissance palazzi.
Visit the Diocesan Museum to see Fra Angelico’s Annunciation.
Walk Cortona’s medieval walls for countryside views.
Food CultureTuscan cuisine here is hearty and rustic: ribollita soup, wild boar ragù, pecorino cheese, and excellent local wines.
Where to Eat
Osteria del Teatro (Cortona) – Refined Tuscan dining in an 18th-century theatre. Try the pici pasta with truffles or the duck ragu.
Da Muzzicone (Castiglion Fiorentino) – Fantastic traditional trattoria serving some of the best Bistecca Fiorentina in Tuscany!
La Bucaccia (Cortona) – Elevated Tuscan classics in an intimate venue within a 13th century mansion
Organika ( Cortona ) - Gorgeous location just outside town walls, with seasonally inspired menus, and local ingredients,request a table on the terrace in the warmer months for stunning sunset views.
Where to Stay
Monastero di Cortona Hotel & Spa – Located in an ancient monastery with garden.
Relais Chateaux Il Falconiere – Magnificent 17th Century Villa transformed into an exclusive residence with stunning Michelin star restaurant
Off the Beaten Track
Hike between the two towns — a scenic trail winds through olive groves and vineyards, taking about 3 hours.
How to Get There by Train
Take a regional train from Florence to Castiglion Fiorentino (~1h 20m). Continue to Camucia-Cortona station (10 minutes). Local buses or taxis take you up the hill to Cortona’s centre.
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