Cortona: Day Trips and Tours from Florence

The enchanting hilltop town of Cortona is one of Tuscany’s hidden gems. Often overlooked in favor of places like Siena and Lucca, Cortona has an identity all of its own.

Rich in culture and steeped in tradition, the walled town is full of hidden piazzas and Gothic churches. You’ll be able to take in all the main sights on a day trip to Cortona from Florence, including the fortress and cloisters.

You can read our comprehensive guide for information and details about Cortona, one of the most enchanting destinations for day trips from Florence.

Where is Cortona located and how do I get there from Florence?

You’ll find Cortona in Tuscany’s Arezzo province, hidden away in the Chiana Valley. It’s an easy road trip from Florence, with dreamy views to sweeten the deal.

From Florence to Cortona by car

The journey to Cortona by road takes about 1.5 hours. There are plenty of pretty villages and viewpoints to stop at on the way if you fancy a break.

To reach Cortona from the city, take the A1 south before turning off at Bettolle in the direction of Cortona. There is a parking area outside the main town gates.

From Florence to Cortona by train

You can reach Cortona by train, with the fastest services taking just 1 hour. There are multiple departures from Florence every day making this a hassle-free way to visit the hilltop town.

The train station in Cortona is outside the city walls, so you’ll need to hop on a bus to reach the historic center.

Guided tour to Cortona from Florence

The most comfortable way to explore is on a Cortona day tour from Florence. You’ll enjoy scenic road transfers, and some operators offer pickups from your hotel.

These excursions last a full day and often include stops at other nearby locations.

What is the typical itinerary of a day tour to Cortona from Florence?

Day trips to Cortona begin with a road transfer by minivan or coach, departing Florence after breakfast. Some tours include hotel transfers, while others leave from a convenient meeting point in the city center.

After a scenic countryside drive, you’ll arrive in Cortona, ready to explore. Enjoy a guided tour around the historic heart before having free time to wander at leisure.

The day trip continues with a stop in either Assisi or Montepulciano, depending on the provider itinerary. Private tours can also include Siena for those who want to see as much as possible.

You’ll be dropped back in Florence in the evening in time for dinner.

What are the most popular tours to Cortona from Florence?

There are three types of day tours to Cortona from Florence. Group visits are the most popular, but private and semi-private trips are also available.

Guided group tour to Cortona plus Assisi from Florence

The most common Cortona excursions are the group tours, as traveling with others means cheaper prices. There is usually a maximum of 30 participants on these trips, with travel in an air-conditioned coach.

Group tours include all transportation and a professional guide, so everything is taken care of. You just need to show up and enjoy the ride.

Semi-private trip to Cortona plus Siena & Montepulciano from Florence

If you prefer a more exclusive experience but don’t want to blow the budget, semi-private tours are the answer. You will be journeying with other people, but the minivans have a maximum capacity of just eight passengers. This ensures the trip remains personal.

These Cortona day tours usually include orientation walks at each location, to help you get a feel for the places you’re visiting.

Private tour to Cortona from Florence

If you want to go all out and enjoy a luxury transfer for just you and your group, private tours to Cortona tick all the boxes. You can ask your driver-guide all the questions you can conjure.

There will be some flexibility with the schedule, and visits to other locations along the route can also be included. Assisi and Montepulciano are popular additions.

How much does a tour to Cortona from Florence cost?

Cortona day trips that also include a visit to Assisi cost €90 per participant. This is a group tour with a maximum of 30 people. Coach travel, a guide, and church entrance fees are covered.

For the semi-private tours that take in Siena and Montepulciano as well as Cortona, expect to pay €260 per person. There is capacity for eight passengers in the minivan, making the experience more exclusive than the standard group tours. Lunch, drinks and orientation walks are included.

The private Cortona day tours with an Assisi extension cost €420 per person, while the trips that include Montepulciano are €300. You will have your own private vehicle with hotel pickups offered for your convenience.

What will I see and do in Cortona?

Known as the setting for the “Under the Tuscan Sun” film, Cortona is packed with history, nature and fine views. On a day tour from Florence to Cortona, you’ll take in the main attractions and get a feel for this alluring hilltop settlement.

Time appears to have stood still in this ancient walled town. The cobblestone streets and flamboyant architecture have been attracting visitors for centuries, drawing them into the medieval Tuscan world. Markets and cafés just add to the vibe.

Some of the highlights of your jaunt to Cortona will include:

Convent delle Celle

This 13th-century cloister was founded by St. Francis himself and is one of the top attractions in Cortona. Beautifully located beside a stream on the slopes of Monte Sant’Egidio, this tranquil hermitage was formerly home to Franciscan monks.

You can see the church and several of the original sleeping cells, including one belonging to St. Francis. Little has changed here over the centuries, so the ambiance is rather special. The views from here are some of the best in town too.

Fortress of Girifalco

Constructed in the 11th century and later modified by Grande Duke Cosimo of the Medici dynasty, the fortress was built to protect Cortona. Today it’s a cultural center but you can still see the guardhouse, keep and courtyard as they were back in the day.

The fortress sits within the town walls and is a popular viewpoint for photographing the rolling green landscapes of Tuscany.

When is the best time to visit Cortona?

The Tuscan weather is some of the best in Europe, so day trips from Florence to Cortona are great all year round.

Spring and summer are the most popular times to visit when it’s warm and sunny. Yet even in the peak months of June and July, Cortona doesn’t get as busy as Florence.

Can I book excursions to Cortona from other cities in Italy?

Yes, there are other tours departing from several other cities in Italy:

• Day trips to Cortona from Siena

Travel tips

• Cortona day trips from Florence are popular so book ahead if you can. By searching online you’ll be able to hunt down the cheapest deals.
• To enter the churches, you will need to cover your knees and shoulders.
• Food isn’t included on most tours, but you will be able to buy lunch locally at a café or restaurant.
• You’ll be doing a fair amount of walking so comfortable footwear is advised.