Cortona Ultimate Travel Guide 2026: Top Things to Do in Tuscany's Beautiful Hill Town
Timeless Wanderers: Updated April 5, 2026
From Under the Tuscan Sun to Today
Cortona is one of the absolute highlights of Tuscany.
We love this romantic hilltop town in southern Tuscany.
When we bought our apartment in Tuscany, Cortona was high on our list of possibilities.
In the end, we chose Lucca, mainly because of its location and easy access to the rest of Italy.
That said, we haven’t completely ruled out Cortona for the future.
Like many people, it was Frances Mayes’ book Under the Tuscan Sun that first drew us here.
I’m pretty sure my wife has read the book and watched the movie a hundred times over the years. I must admit, I’ve seen it more than a few times myself.
Since our first visit, we’ve returned to Cortona many times.
There’s something about the town’s peaceful atmosphere and familiar surroundings that keeps calling us back.
It’s hard not to fall in love with the noble palaces, beautiful piazzas, narrow lanes, and stepped streets that wind their way through the historic centre.
Then there’s the simple pleasure of small-town Italian life.
Long lunches, excellent local wine, and lazy afternoons spent sitting in the piazza watching the wonderfully chaotic Italian world go by.
That’s what keeps bringing us back.
In this Cortona travel guide, we’ll share the best things to do, where to stay, how to get here, the best places to eat, and how much time you should allow to experience one of Tuscany’s most charming hill towns.
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After more than 20 years of travelling to Tuscany—and loving it so much we decided to make it our home—we now live here and explore the region at a relaxed, local pace.
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What Makes Cortona So Special?
Cortona is located in the south-eastern corner of Tuscany, in the province of Arezzo, about 105 km from Florence.
It doesn’t attract quite as many visitors as some of Tuscany’s more famous hill towns, but don’t expect it to be quiet or empty.
Cortona has a steady flow of travellers, many drawn here by its atmosphere, history, and its connection to Under the Tuscan Sun.
One of the most recognisable spots is Villa Bramasole, made famous by the book and film.
It still attracts visitors who want to see the setting that inspired so many people to fall in love with Tuscany.
Cortona has incredibly deep roots.
It dates back to the 4th century BC and was an important Etruscan city long before the Romans arrived.
The Etruscans were one of the earliest civilisations in this part of Italy, and their influence can still be felt throughout the region today.
Set high on a hilltop, Cortona is a town best explored on foot.
Expect steep, winding streets, stone alleyways, and sudden viewpoints that open out across the Val di Chiana and beyond.
It’s this combination of history, atmosphere, and incredible views that makes Cortona one of the most beautiful and memorable towns in Tuscany.
GETTING TO CORTONA
BY CAR
The easiest way to get to Cortona is to drive here, from Florence is an easy one down the A1 Auto Strande.
For Cortona you’ll need to exit at Betolle Valdichiana it should take about an hour.
CAR RENTAL
I recommend using the following 2 car rental websites.
Discover Cars includes offerings from all the major international rental companies as well as lots of smaller local agencies, which often have much better pricing.
Rental Cars is very similar although they tend to list mostly larger companies.
Owned by Booking.com so it’s certainly backed by a familiar and reputable brand.
BY TRAIN
The two closest train stations to Cortona are the terentola station (on the terontola Perugia – Assisi Railway line and the Florence – Rome railway line) and the Camucia station (on the Florence – Rome Railway Line) from both station, you can get to the city centre by bus or Taxi.
You can book you tickets directly with the service provider. We use OMIO We find their website is easy and straight forward to navigate.
BY BUS
The best way to get to Cortona by bus is to take the train to the Camucia or Terontola stations and then take the bus to the historic city centre.
DRIVING DISTANCES
Montepulciano – 31Km
Moutalcino – 66Km
Pienza 50Km
Arezzo 30Km
Florence 120Km
Siena 75Km
Car rental – If you plan to visit countryside towns and vineyards, a rental car is invaluable.
Things to do in CORTONA
Piazza Della Repubbica
Is what you image when you think of Italy, it’s small and charming and full of life.
Enjoy sitting savouring a cappuccino and cornetto at one of the cafes or just relaxing on the steps while taking in a little people watching Italian style.
Meet the Etruscans at Muso Dell’ Accademia Etrusca (MAEC)
From the eight century B.C. Cortona was a member of the Etruscan League of cities, and jewellery, bronzes, and other local finds are on display at this sophisticated Museum in the beautiful Palazzo Casali.
The stand out is a massive, 2500-year-old oil-lamp chandelier that would be the prize of any modern home-design showroom.
It is a large museum spanning over several floors.
A visit here lasts anywhere from 30 minutes to an hour or longer, depending on your interest in Etruscan history.
Read this next
8 Stunning Towns To Visit In Tuscany (2026 Guide)
Visit the Diocesan Museum
This art museum is located on Piazza del Duomo on the site of the church of Jesus.
This museum contains notable works of art, including a cross paintreated by Pietro Lorenzetti, the Cortona trip tych by Fra Angelico, and Madonna and child by Niccolo di Segna.
STROLL ALONG VIA NAZIONALE
Stroll down the only flat street in town, Via Nazionale is the main thoroughfare through Cortona.
Along this pedstration street are small restaurants, shops, and places to go wine tasting.
Via Nazionale connects two of the most popular Piazzas in town, Piazza Garibaldi and Piazza delca Repubblica.
TO THE TOP OF CORTONA
Basilica Di Santa Margherita and GIRIFALCO Medici Fortress, taking the walk up to the very top of Cortona’s hill to see Balilica di Santa Margherita will be something that you will remember forever.
This is one of our favorite churches and the view is breathtaking.
The walk up, although a bit of a trek, is lovely and takes you to some quaint and quite areas of town.
If you are feeling a little more adventurous and still have a little more hike in you, you can continue up on the hill to side of the churches to see the GIRIFALCO Fortress.
VILLA BRAMASOLE
Villa Bramasole is featured in the movie UNDER THE Tuscan Sun filmed in 2003 starring Dianne Lane, this movie is based on Frances Mayes Memoir.
This movie put Cortona on the tourist map and now people travel here from all over the world just to see the villa.
If you head out of town through the city park it is about a 30min (2KM) walk. You can find it on google map if you search Bramasole.
I wouldn’t do this walk in the heat of the day and make sure to bring some water and a snack as there isn’t anything along the way except some benches to sit on and enjoy the views.
SHOPPING IN CORTONA
There are so many beautiful and unique shops in Cortona as well as some great cafes and restaurants.
There are some souvenir shops in Cortona, but you’ll find wonderful art galleries small boutique shops selling everything from food to clothing to shoes, and places to go wine tasting.
Vini Di Toscana is a wine shop that offers tastings. It is located on Via Nazionale.
We tasted beautiful Tuscan wine, Brunello di Montalcino, Sryah, and others.
As a souvenir from Cortona purchase a bottle of the Bramasole, a Syrah produced in Cortona.
Cortona is just the perfect town to go exploring and get lost in.
HOW LONG TO SPEND IN CORTONA
Cortona is well known as a beautiful Tuscan Hill town, so it’s very popular with day trippers as far away as Florence.
Cortona can be seen in one lovely day but I think it is special enough to give it two if you have time.
A little more time to linger on it’s streets or take Cypress lined walk out to see Frances Mayes idealistic Tuscan home.
This town is a place to relax, a place to sit in the Piazza or walk through the market leisurely.
A place to take in breathtaking views while listening to the fountains as you have a picnic in the park, a place where you can walk through the back streets discovering Italy.
This place is a place to see.
So, if you only have one day Cortona – take it. But if you have two ……even better.
WHERE TO STAY
Cortona is small and very much on the map for tourists, so don’t be surprised if you can’t find cheap accommodation if staying here.
Of course, being a tourist destination means it has lots of options, many of which are very nice, so you have a good selection to choose from.
Below are some places in town that we would recommend:
Villa Di Piazzano is just at the bottom of the hill that Cortona sits atop. Villa di Piazzano is a fantastic 5-star hotel set inside a noble villa with manicured gardens and grounds.
Monesary Di Cortona Hotel and Spa
This Boutique Hotel – kids free hotel is located in an ancient Monastery and boasts a beautiful garden.
Hotel San Michelle is located inside one of the oldest buildings in Cortona, the ancient Baldelli Palace, located right in town.
Stylish apartments in the center of town are attractive and very comfortable, you will be tempted to settle in for a very long time.
In the delightful full historic center, a very comfortable apartment and has every comfort you need.
RESTAURANT AND DINING
A favourite in any Cortona menu is Chiana beef which hails from the valley below town.
These huge T-Bone, simply grilled, usually serves two.
They’re often accompanied by Cortona’s own doc red wines.
For lunch or dinner consider trying any of the following restaurants.
TRATTORIA DARDANO
Specialises in grilled meals – chicken, duck, beef, quinea hen all locally raised – served ina homey setting alongside other Tuscan classics.
OSTERIA AL TATRO
Character filled candle lit rooms are the setting for the creations of chef Emiliano Rossi, who pairs local meats and the freshest produce with Cortona wines.
TRATTORIA LA GROTTA
Any meal at Trattoria La Grotta, whether you enjoy it in a medieval, brick vaulted dining room or in the courtyard in good weather, should include the house specialty, light as a feather Gnoochi.
RISTORANTE LA LOGGETTA
This is one of our favourite restaurants, we always seem to come back here, either for lunch or Dinner, we just love the setting above
PIAZZA DELLA REPUBBLILA
The location alone makes it special. But the real highlight are the steaks and the local produce that do justice do the setting.
TRATTORIA TOSCANO
Lays claims to introduce Cortona to the citys now favorite pasta, Picci alla fumato, a very rich combination of ham, cheese, and cream.
DAY TRIPS FROM CORTONA
Several Tuscan hill towns can be added to your visit to Cortona.
Here are some of our favorites.
ASSISI
Assisi is located in Umbria, an hour from Cortona by car.
This city, which is the birthplace of St. Francis, is also one of Europe’s most popular Pilgrimage sites.
People come from around the world to pay homage to the humble saint at the imposing Medieval Basiclica where he is buried.
AREZZO
Arezzo is a 45-minute drive from Cortona, Arrezzo is another beautiful Tuscan town that is a delight to visit.
Beyond the modern outskirts is a beautiful Medieval city centre.
Welcoming cobblestone streets filled with several churches and art treasures.
Wander through the historic city center, and have lunch or dinner in the main square.
PIENZA
Pienza is about an hour from Cortona, it’s a beautiful small town, with a population of about 2000 surrounded by the charming hilly landscape of Val d’orcia, this Renaissance town is even listed as a Unesco world heritage site.
On a trip to Pienza, he is sure to try the excellent pecorino cheese, a semi-hard sheep milk cheese that is considered the best in Tuscany.
MONTEPULCIANO
Montepulciano is only about half an hour from Cortona, the beautiful hill town is famous for its wines, Vino Nobile and Rosso di Montepulciano.
Go wine tasting, tour the underground wine cellars, and stroll the picturesque streets.
TOURS OF CORTONA
There are lots of tours that include Cortona. From Florence, visit both Cortona and Montepulciano.
Cortona you can take a 3 hour private walking tour or a cooking class.
Read our Full Guide on
Tuscany’s 5 Best Hilltop Towns: Explore Italy’s Most Scenic Villages
FAQs – Visiting Cortona, Tuscany
1. Is Cortona worth visiting?
Absolutely. Cortona combines Tuscan charm, breathtaking views, and rich history—all in a walkable hilltop town that feels authentic and relaxed.
2. How many days should I spend in Cortona?
Two to three days is ideal to explore the main sights, enjoy local cuisine, and take in nearby countryside views.
3. What is Cortona famous for?
Cortona is known for its Etruscan heritage, stunning views over Val di Chiana, and for inspiring the movie and book Under the Tuscan Sun.
4. How do I get to Cortona from Florence?
Take a train to Camucia-Cortona (about 1.5 hours), then a taxi or local bus to the hilltop center. Driving takes around 1 hour and 45 minutes.
5. Is parking easy in Cortona?
Parking is available just outside the old town walls, with shuttle buses connecting to the main piazza. Avoid driving in the narrow central streets.
6. What are the best things to do in Cortona?
Explore the MAEC Museum, Basilica di Santa Margherita, and Fortezza del Girifalco. Don’t miss sunset from Piazza Garibaldi.
7. Is Cortona good for families?
Yes — its walkable streets, family-friendly restaurants, and cultural attractions make it perfect for travelers with children.
8. Can I visit Cortona as a day trip?
Yes, Cortona makes an excellent day trip from Florence, Siena, or Perugia. However, an overnight stay lets you enjoy the peaceful evening ambiance.
Car rental – If you plan to visit countryside towns and vineyards, a rental car is invaluable.
Do You Need Travel Insurance for Tuscany?
(Short Answer: Yes — It’s Still a Smart Idea)
Travel insurance isn’t legally required to visit Tuscany, but it’s one of the smartest things you can have when travelling in Italy.
Even in a relaxed destination like Tuscany, things can go wrong — from delayed flights and lost luggage to medical issues, rental car damage, or unexpected trip cancellations.
And while Italy has excellent healthcare, medical treatment for visitors can still be costly without proper coverage.
As long-term travellers living in Italy, we’ve found SafetyWing to be a practical option for trips around Europe, offering coverage for medical care, travel delays, and lost belongings without complicated fine print.
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It’s the kind of insurance you hope you never need—but you’ll be very glad you have if something unexpected happens.
Final Thoughts on Cortona
Cortona is a charming hilltop town that perfectly captures the essence of Tuscany.
With its narrow medieval streets, historic piazzas, and views over the Val di Chiana, it’s both picturesque and inviting.
The town’s vibrant culture, artisan shops, and local trattorias create an authentic Tuscan experience, while landmarks like the Piazza della Repubblica and the Diocesan Museum highlight its rich history.
Cortona is ideal for wandering at a leisurely pace, enjoying scenic vistas, and immersing yourself in Tuscan life.
Whether visiting for a day or staying longer, Cortona leaves a lasting impression of beauty, history, and charm
PLAN YOUR TUSCANY ADVENTURE
These are our favorite companies we use when planning a trip, they consistently have the best prices, great customer service, and overall, are better than their competitors.
BOOK YOUR FLIGHT – Going is a great search engine if you are flexible about your travel destination and dates. Sign up for their newsletter and get the latest deals on destinations around the world. GOING is our new go to.
CAR RENTAL – We recommend using Discover Cars or Rental Cars when booking a car rental, they work with hundreds of companies worldwide to help you find the best car for your needs.
TRAINS – OMIO – is our favorite, this site is very reliable and easy to use.
BUS – OMIO – this website allows you to book train or bus tickets to travel from city to city the best and cheapest way. FLIXBUS is another terrific website with routes between 20 European countries.
ACCOMMODATIONS
BOOKING.com – is our go to for hotel searches around the world, we find they always have the cheapest rates and offer different payment options. In addition, VRBO is another terrific website for all types of accommodations.
HOSTELWORLD – is great if you’re traveling on a budget, and if you need a cheap place to stay.
SIGHTSEEING TOURS
GET YOUR GUIDE – is our favorite; they have stacks of tours and excursions available in cities all over the world. VIATOR is another great website for all types of tours.
TAKE WALKS – This walking tour company provides inside access to attractions and places you can’t get elsewhere.
TRAVEL INSURANCE
SAFETY WING – is our go to travel medical insurance company, especially for longer trips. You can either purchase a monthly plan or a plan for specific trip dates (i.e. 1-2 week trips). They cover people from all over the world, while outside their home country.
ARC’TERYX – is a go to reliable brand for outdoor adventure and travel, their wide range includes light weight durable, easy to clean travel gear.
Check out our RESOURCE PAGE for more additional planning.