All you need to know to make the most of your stay in Cortona and surrounding area: the best things to do, the best day trips, my recommendations for restaurants, accommodation, tours and experiences, based on our own travels.
The hilltop town of Cortona is one of the most beautiful villages in Tuscany and a fantastic place to call home while vacationing in Tuscany.
Cortona is a delight.
Ancient, atmospheric and on a scenic hilltop, it is everything you hope a Tuscan town will be: beautiful medieval streets, sweeping views over rolling countryside, delicious food, and a pace of life that makes you want to slow right down and stay.
But what makes Cortona even more special is its position.
Sitting on the border between Tuscany and Umbria, Cortona is surrounded by some of the most beautiful countryside in central Italy.
It is close to extraordinary wine country, gorgeous smaller hilltop towns, one of the most beloved lakes in the region, and easy driving distance from some of the great cities of Tuscany.
By staying in the Cortona area, you have the best of this part of Italy at your fingertips.
I know this well as we are lucky to have friends in the area who are always more than willing to show us all the gems that make this area special and we all love it here.
The adults love the sightseeing and the wine, the kids love the long summer days in the pool and we all love the slow paces, spontaneous exploring Tuscany lends itself to.
Over the course of the years, I have visited more times than I can remember and I always recommend Cortona to friends looking for a Tuscan escape.
Based on my own family’s experiences, this is my guide to the best things to do in Cortona and surrounding area!
Good to know! Cortona is well known to international tourism so you are not off the beaten track by any stretch of the imagination. However, from here you have access to spots that are rural and local; so, while not in a ‘hidden gem’, you will not be in maddening crowds either!
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Travel guide to the Cortona area TL;DR
- Cortona is one of the most beautiful hilltop towns in Tuscany, with important Etruscan history and wonderful food
- The area around Cortona is blessed with rolling hills, vineyards, gorgeous smaller villages and a beautiful lake, perfect for a relaxed, immersive Tuscan stay
- Cortona is a great base for exploring hilltop towns, parts of Umbrian, wine country and even the cities of Arezzo and Siena, all within easy reach
- The best way to visit Cortona and surrounding area is by car. I recommend renting one via Discover Cars which allows you to filter by size, deposit and card type.
- The best way to enjoy this area is by finding accommodation in an agriturismo or country property, so you can immerse yourself in the Tuscan countryside, escape the busiest tourist areas and have easy access to all the region has to offer
- My favourite experiences here are town-hopping through the Valdichiana (the drives alone are worth it!), wine tasting at a local Cortona DOC winery, truffle hunting, cooking classes and just relaxing at the pool.
- The best seasons to visit are spring and autumn for sightseeing; summer is hot but wonderful if you are staying in the countryside with a pool. Winter is more limited but has some lovely seasonal events such as local food fairs
Where to stay in and near Cortona
Lovely places for a Cortona stay are:
Villa Borgo San Pietro – immediately outside the town of Cortona, this Borgo is a delight. It is family friendly and offers beautiful rooms in typical Tuscan style, with air conditioning in summer, a large green park surrounding the property with seasonal outdoor pool, table tennis, football pitch and even a gym on site. On request they can help organise activities such as horse riding in the area.
Agriturismo I Pagliai – a lovely country property close to Cortona offering beautiful rooms, pleasant green grounds all around with outdoor pool and a restaurant on site for breakfast and dinner (date dependant: always check restaurant operating season with the owners for you specific dates). The agriturismo is kid-friendly.
Monastero San Silvestro – a wonderful option in the Cortona countryside (car needed) with well appointed apartments in typical Tuscan style, lovely outdoor space, outdoor seasonal pool and a fantastic buffer breakfast. Family friendly.
Podere Peciano – a lovely, kid friendly and dog friendly agriturismo with pretty apartments, a lovely outdoor seasonal pool, kids play equipment, and bbq area.
Il Falconiere – stunning Relais & Chateaux property with beautiful rooms, grounds, a Michelin restaurant, spa area and all the services you may need – perfect for a special stay. The same family also own the Baracchi winery which is open to guests for visits. Il Falconiere is especially suited to couples and travelers looking for an upscale stay.
In Cortona itself, which is especially handy if you are visiting off season or want to have the tows cafes and restaurants on your doorstep, Hotel San Michele is a good central address
Best tours and structured experiences in Cortona and nearby
Cortona and its surrounding area are wonderful for interactive and hands-on activities.
My favorite way to enjoy the area is to keep the schedule loose, yet plan one or two structured experiences to get a little deeper into the culture of the area.
This area is all about the land and its products so cooking classes and wines are the most popular offerings. Museums and ancient towns are easy to visit without a tour.
This is my shortlist of some of my favourites – Fattoria Bistecca has a specific kids’ vocation with activaties for kids, but all the tours on the list are kid friendly and kids can tag along.
| Activity and Link | Kid-Friendly | Description |
| Cooking Class in a Tuscan villa | Yes – family friendly environment | Half day food experience with Tuscany cooking class and lunch in a welcoming, homely environment |
| Wine tour and tasting in the woman-led Cantina Buccelletti | Yes – reduced price for kids | Women-led winery and cellar offering tastings (with and without a tour) and option for lunch |
| Farm visit to didactic farm ‘Fattoria Bistecca‘ | Yes, FOR kids! | A lovely place for families where the kids can meet the animals and the whole family can learn about cheese making or take a cooking class with local products |
| Go Truffle hunting | Yes, if they love dogs | A fun way to spend time outside in the company of a furry dog and their owner looking for truffles (with meal after) |
| Wine tasting and cooking class at Cantina Canaio | Yes, reduced rate for kids) | A family-run winery producing Cortona DOC Syrah, combining a winery tour with a cooking class and lunch. |
| Valdichiana E-Bike tour | Older kids only due to e-bike minimum age regulations | A great and active way to explore Val di Chiana, with the option adding lunch in a local agriturismo |
The best things to do in Cortona and surrounding area
Visit Cortona town
A stay in the Cortona area starts, of course, with Cortona itself.
One of the oldest towns in Tuscany, with origins stretching back to the Etruscans, Cortona sits high on a hill with staggering views over the Val di Chiana: its medieval streets, beautiful piazzas and important museums make it a destination in its own right.
Cortona became know to tourism many years ago as a setting for novels and movies that chose it for its undeniable charm and quintessentially ‘Tuscan feel’ and this has partially shaped the feel for the place.
However, despite seeing more tourism than other center sin the area, it is still very much an enjoyable place and worth seeing for its history especially.
In my opinion, it is particularly nice to visit its museums and then sip aperitivo outside: we like to choose one on the side streets for the less ‘see and to be seen’ options vs the main square. The thing to order is ‘ciaccia’ the local focaccia, perfect with a glass of wine or spritz!
I have a full guide to Cortona town here, covering all the best things to see and do, where to eat and practical tips for your visit.
Discover the villages of Val di Chiana
One of the greatest pleasures of staying in the Cortona area is having the time to potter between the beautiful smaller towns of the Valdichiana, a wide agricultural valley dotted with hilltop villages that most tourists never reach.
The area never became as high profile of Chianti or Val D’Orcia and this is one of the great mystery of tourism trends: when you are here, you quickly wonder why you hand’t heard much, if anything, about it before! Maybe we should keep it quiet and leave it that way…
All these villages are within easy reach from Cortona by car and make for lovely excursions.
In Valdichiana, my favourite are:
Castiglion Fiorentino – my first recommendation and one of my favourites in the area. The village is an Etruscan-origin hilltop town has a beautiful Vasari loggia, a charming main piazza and a small fortress, the Cassero, with panoramic views over the valley. It is quiet, authentic and wonderfully unspoilt. A lovely destination for a morning trip, you can come over and have coffee and a stroll with leisure.
Lucignano is tiny, perfectly circular in layout and utterly charming. Its medieval streets spiral inward like a shell and is a delight of flower post and cure corners.
At its heart sits a wonderful small museum containing the Albero d’Oro, the Tree of Love, which is a breathtaking Gothic golden reliquary that is said to bring luck to lovers. Many couples make a special detour here to see it. Lucignano is small enough to see quickly but special enough to stay for lunch.
Monte San Savino is a lesser-known gem, a quieter town with another beautiful Vasari loggia and a truly peculiar underground area with water! Another off the beaten path small village well worth your time.
Explore Val d’Orcia villages
Val d’Orcia is one of the most famous parts of Tuscany – when you see rolling golden hills and cypress trees… that’s usually Val d’Orcia!
The area is worth a stay in itself but several of its gems are also easy to visit for Cortona and worth the day.
In Val d’Orcia, the most beautiful and easiest to reach from Cortona are Montepulciano and Pienza, stunning hilltop towns blessed with incredible views and famous for their architecture, wines and the quintessential Tuscan feel we all long for!
Montepulciano is one of the great hilltop towns of southern Tuscany and, at around 40 minutes from Cortona, an easy and very rewarding day trip.
The town is famous above all for its wine — Vino Nobile di Montepulciano DOCG, one of Italy’s greatest reds — and a visit to its underground wine cellars is one of the most atmospheric and memorable experiences in the region.
The main street climbs steeply through the town, lined with wine shops, artisan producers and beautiful Renaissance palazzi, leading up to the magnificent Piazza Grande at the top, which is one of my favorite piazzas in Italy. It has a wonderful appearance, vibe and the ancient well is stunning to see!
If you visit, don’t miss the view from the top of the tower: on a clear day you can see for miles across the Val d’Orcia. You can find my full guide to Montepulciano here.
Pienza is smaller but also very well worth a stop.
About an hour from Cortona, Pienza is one of the most perfect small towns in Italy and one that was built just with this aim: Pope Pius II in the 15th century wanted to transform it in a ‘perfect town’. With beautiful main square, stunning views and a very particular specialty, pecorino cheese, many would agree he succeeded!
If you visit, the thing to do is taste as many types of pecorino as you can find (aged, fresh, with truffle, with chilli — there is a whole world of it here), wander the beautiful city walls for views over the Val d’Orcia, and pick up some shopping.
The town is small and can be seen in a couple of hours.
It is easy to combine it with Montalcino or Montepulciano, which are nearby and famous for Vino Nobile and Brunello, two of Italy’s greatest red wines. Find my guide to Pienza here.
Spend a day at Lake Trasimeno
Just 20-25 minutes from Cortona, Lake Trasimeno is the largest lake in central Italy and a pleasant yet somehow low key destination.
The lake has a completely different feel from the hilltop towns: wide, peaceful, with small towns dotted around its shores and small islands rising from its centre.
It is a nice contrast after a few days of meandering medieval streets and feels more local than most other places in the area as it is off the main tourist track.
The nicest things to do here are: explore the lakeside town of Castiglione del Lago, catch the ferry to Isola Maggiore — a tiny island with a lovely village — hire a kayak or paddleboat on the water, and have a long lazy lunch at one of the lakeside restaurants.
For families, the lake is wonderful: easy, flat, and children can run along the shore and get on the water. The lake is local in feel and despite the highly doctored images of it on the web, it is not a glam, Lake Como lookalike! It’s a low key, local destination aways form the glitz and crowds of mass tourism, suitable for a relaxed family day out.
Explore Umbria towns
Cortona is in Tuscany but close to Umbria, the landlocked beautiful region to its East.
Umbria has a lot in common with Tuscany but it is also very different in feel and well worth a vacation in its own right. The feel here is more local, less airbrushed and while you’d need longer to have a proper sense of the region, from Cortona you can have a first taste for it!
As well as Lake Trasimeno, easy and worth seeing from Cortona are the towns of Gubbio (amazing, my favorite!), Citta’ di Castello which is a real gem, Perugia and of course Assisi.
Visit Arezzo
About 35-40 minutes from Cortona, Arezzo is one of the great Tuscan cities and well worth a full day of your time. It is significantly less visited than Florence or Siena, which means you can enjoy it at a genuinely leisurely pace.
The city has a beautiful historic centre, a spectacular main square, a wonderful cathedral, and the extraordinary frescoes of Piero della Francesca.
Arezzo is also famous for its antique market, held in and around Piazza Grande on the first weekend of every month, or if you happen to be here around Christmas, Arezzo also has one of the best Christmas markets in Tuscany!
Go wine tasting: Cortona DOC
One of the most delightful surprises of the Cortona area is its wine.
Cortona has its own DOC and its signature grape is Syrah, which produces wines of real character and complexity. Tasting them, especially at the wineries where they are made, is one of the great pleasures of staying here.
The best way to visit wineries in this area is by car (make sure one of you is designated driver): booking is recommended and usually even required. These are working wineries first and hospitality places next: booking is the best way to make sure someone is there to meet you.
Wineries near Cortona I recommend for a visit or tasting:
- Cantina Buccelletti – a women led winery offering tours and tasting in various formats
- Cantina Canaio — a small, family-run estate producing 100% Syrah and Merlot wines with a wonderful atmosphere and exceptional hospitality. Their combined winery tour, cooking class and lunch is one of the best experiences in the area.
- Stefano Amerighi — a leading biodynamic producer, highly regarded for exceptional Cortona Syrah.
- Baracchi Winery / Il Falconiere — the estate winery of the famous Relais & Châteaux property, beautiful setting, more upscale option.
- Baldetti — a well-run family estate in the heart of the Cortona countryside with good guided tastings.
Tip if visiting with kids: wineries in Italy are generally very family-friendly. Find here >> my guide to wine tasting in Tuscany with kids
Go truffle hunting
Truffle hunting is is a fun and fascinating experience perfect for truffle lovers but also not just! If you have dog lovers in your group, it’s a great excuse to be outside with furry companion!
The experience typically involves a walk in the woods with an expert hunter and his trained dogs, watching them sniff out the precious funghi, learning about truffle varieties and traditions, and then tasting the results.
If your kids don’t truffles, tell them ahead so they can agree alternative with you.
Just be aware that the season matters: always double check before booking also because truffles are pretty temperamental about what they need to thrive.
Take a scenic drive
The countryside around Cortona is some of the most beautiful in Italy, and one of the most pleasurable things you can do here is simply drive through it slowly, with the windows down, stopping wherever takes your fancy.
The classic route from Cortona toward Castiglion Fiorentino (about 12km along the SR71 through vineyards and hills) is beautiful and worth doing even if you don’t stop.
The drive down toward Lake Trasimeno with wide views over the Val di Chiana is equally stunning.
And the roads around Montepulciano and toward the Val d’Orcia, with their famous cypress-lined avenues and perfectly composed Tuscan panoramas, are simply unforgettable.
My advice: build in at least one afternoon with no agenda other than driving. Stop for a coffee in a village you’ve never heard of, buy a bottle of wine directly from a roadside cantina, find a viewpoint and sit with it for a while. This is what this area is really about.
Where to eat in and near Cortona
The food of this area is deeply, satisfyingly Tuscan: earthy, seasonal, filling and delicious. You can eat very well here at every price point. Some recommendations you may enjoy, some a drive away (but worth it!):
Osteria del Teatro – in Cortona town, this is a delicious traditional restaurant with a theatrical theme. The dishes are strongly rooted in local tradition and products and change with the season. Most of the seating is indoors, with few very sough after tables outside.
Locanda del Molino, delicious rustic restaurant in an old mill
La Bucaccia, a small and delicious restaurant in Cortona itself, serving hight quality local specialties
Le Terre dei Cavalieri – already mentioned above as a lovely place to call home while in this area, Le Terre dei Cavalieri also has a restaurant open to non guests making beautiful and delicious dishes inspired by the tradition yet updated by the creaitivity of their chef. The menu changes seasonally and is inspired by the products of the estate itself.
Il Falconiere – for special occasions. A real treat to the tastebuds as well as the eyes, Il Falconiere is Michelin starred and it’s a place out of a dream. The setting is stunning and quintessentially Tuscan, the dishes are hyper local, many made with product for the estate itself and the cooking excellent: Chianina is a specialty.
Il Conte Matto, in Trequanda, is lovely and also has a wonderful terrace overlooking the hill, a dream on mild, sunny days.
In many cases, wineries in the area also offer light or more substantial lunch as part of their wine tasting offering: a great option especially for days when looking for a light meal or a winery setting with views.
How to get around Cortona and surrounding area
The Cortona area is best explored by car. Driving in this part of Tuscany is genuinely enjoyable — the roads are beautiful, traffic outside of the summer peak is light, and having a car gives you the freedom to stop wherever you like.
As with all historic Tuscan towns, the centres of Cortona and surrounding villages are typically protected by a ZTL (limited traffic zone) and closed to non-resident cars.
Follow the signs for parking (P) and leave the car in the designated areas just outside the town walls — they are well-signposted and usually pay-and-display (bring coins, or check for card payment options).
You can find here >> my tips for driving in Tuscany And here >> my guide to parking in Italy
I hope you enjoyed this guide to the best things to do in Cortona and surrounding area and it helps you plan a wonderful stay. Safe travels!
