4 days in Cortona & Siena Itinerary

4 days in Cortona & Siena Itinerary

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Route & dates

4 days in Cortona & Siena Itinerary

Start: Cortona
— 3 nights
Drive:  1​h 15​min
— 1 day
Drive:  1​h 15​min
End: Cortona


Cortona ©
The hilltop town of Cortona gained international attention as the subject of the 2003 film "Under the Tuscan Sun." With the Chiana Valley and Lake Trasimeno as its backdrop, Cortona is one of Tuscany's hotspots for art and culture.
You'll find plenty of places to visit near Cortona: Fosso Bianco - Bagni San Filippo (in Bagni di San Filippo), Spas (in Chianciano Terme) and Piazza Grande a Montepulciano (in Montepulciano). There's much more to do: steep yourself in history at Eremo Le Celle, take an in-depth tour of MAEC - Museo dell'Accademia Etrusca, admire the verdant scenery at Val d'Orcia, and take in the architecture and atmosphere at Santa Margherita, Cortona.

To see ratings, other places to visit, more things to do, and more tourist information, use the Cortona tour planner .

If you are flying in from United Kingdom, the closest major airports are Perugia San Francesco d'Assisi – Umbria International Airport, Peretola Airport and Federico Fellini International Airport. Cap off your sightseeing on the 19th (Tue) early enough to go by car to Siena.

Things to do in Cortona

Historic Sites Tours Parks

Side Trips

Fosso Bianco - Bagni San Filippo, Piazza Grande a Montepulciano, Piazza Pio II, Spas, Val d'Orcia
Find places to stay May 16 — 19:
Highlights from your plan
Val d'Orcia ©
Val d'Orcia
Eremo Le Celle ©
Eremo Le Celle
Azienda Agricola Leuta ©
Azienda Agricola Leuta


Siena ©
Siena, a medieval Tuscan city, features numerous attractions, including a historic town center, alleyways, towers, and well-preserved buildings.
On the 19th (Tue), take in the architecture and atmosphere at Duomo di Siena, then make a trip to Piazza del Campo, and then savor the flavors at Food & Drink.

For reviews, other places to visit, ratings, and tourist information, go to the Siena day trip website .

Traveling by car from Cortona to Siena takes 1.5 hours. Alternatively, you can do a combination of train and bus; or take a train. In May, plan for daily highs up to 27°C, and evening lows to 13°C. Wrap up your sightseeing on the 19th (Tue) early enough to drive back home.

Things to do in Siena

Historic Sites
Find places to stay May 19 — 20:
Highlights from your plan
Piazza del Campo ©
Piazza del Campo
Duomo di Siena ©
Duomo di Siena