A Stop in Cortona

One of the oldest towns in Italy. Etruscan walls, Renaissance churches and sweeping views over Lake Trasimeno — a hilltop experience unlike any other in Tuscany.

📍 Etruscan Town ⏱ 1–2 Hours Stop 🚗 Private Chauffeur ✅ NCC Licensed since 2004

Why Stop in Cortona

Three Thousand Years of History

Cortona is one of the oldest continuously inhabited towns in Italy. Founded by the Etruscans more than three thousand years ago, it sits on a steep hillside above the Val di Chiana, its ancient walls still encircling the entire town. Few places in Tuscany — or anywhere in Italy — carry such a palpable sense of accumulated history.

The town became internationally famous after Frances Mayes published "Under the Tuscan Sun" in the 1990s, but long before that it was known to art historians for its remarkable collection of Renaissance and medieval art. The Museo Diocesano houses works by Fra Angelico and Pietro Lorenzetti that would be the pride of any major museum. The views from the upper terraces — over Lake Trasimeno, the Val di Chiana and on clear days as far as Umbria — are among the finest in central Italy.

Cortona sits naturally along several routes between Tuscany and Umbria, making it an ideal stop on a longer transfer. Our driver will plan the timing so you have one to two hours to explore the steep lanes, visit the main piazza and take in the views before continuing your journey.

Where to Eat in Cortona Michelin Guide →

Cortona has a surprisingly strong restaurant scene for a town of its size. From traditional Chianina beef trattorias to refined Tuscan cuisine with views over the Val di Chiana — the Michelin Guide lists the best options in town, updated each season.

1–2 hrsRecommended Stop

3000+Years of History

EtruscanFounded By

24/7Available Year-Round

Transfer Routes

Journeys That Pass Through Cortona

Cortona sits at the crossroads of Tuscany and Umbria, making it a natural stop on several routes between central Italy and the Adriatic coast.

Route 01

Florence → Ancona with stop in Cortona

Travelling from Florence to Ancona on the Adriatic coast? The route passes through the Val di Chiana — and Cortona sits perfectly along the way. A stop here adds a genuine cultural highlight to what would otherwise be a purely logistical journey. Walk the Etruscan walls, visit the main piazza and enjoy the views over Lake Trasimeno before continuing east toward the coast.

Florence 📍 Cortona · 1–2 hrs Ancona

⏱ Total: approx. 4–5 hrs with stop 👥 Up to 3 pax · Mercedes E-Class

Route 02

Florence → Rome with stop in Cortona

Rather than driving straight down the motorway from Florence to Rome, break the journey in Cortona — one of the most rewarding hilltop towns in central Italy. Spend an hour exploring the ancient lanes and taking in the views over the Val di Chiana before continuing south to the Italian capital. A far more memorable way to travel between Tuscany and Rome.

Florence 📍 Cortona · 1–2 hrs Rome

⏱ Total: approx. 5–6 hrs with stop 👥 Up to 6 pax · Mercedes Vito / V-Class

Route 03

Spoleto → Florence with stop in Cortona

Leaving the beautiful Umbrian town of Spoleto and heading north to Florence? Cortona sits naturally along the route just across the Tuscan border — a perfect opportunity to combine two of central Italy's most atmospheric hilltop towns in a single journey. The views from Cortona across the Val di Chiana toward Umbria are particularly striking on this route.

Spoleto 📍 Cortona · 1–2 hrs Florence

⏱ Total: approx. 4–5 hrs with stop 👥 Up to 3 pax · Mercedes E-Class

Route 04

Civitavecchia → Florence with stop in Cortona

Arriving at Civitavecchia cruise port and heading north to Florence? The long drive up through Lazio and into Tuscany becomes genuinely rewarding with a stop in Cortona. Break the journey in one of Italy's oldest towns — walk the Etruscan walls, visit the Piazza della Repubblica and enjoy lunch with a view — before completing the final leg to Florence.

Civitavecchia Port 📍 Cortona · 1–2 hrs Florence

⏱ Total: approx. 5–6 hrs with stop 👥 Up to 6 pax · Mercedes Vito / V-Class

What to See in Cortona

Make the Most of Your Stop

One to two hours is enough to experience the best of Cortona. Here is what we recommend to first-time visitors.