If you’re lucky enough to be planning to spend any time in Italy in the foreseeable future, Cortona is one of the best small towns in Tuscany if you’re considering the addition of Tuscany to your Italy itinerary. There are so many charming Tuscany towns that it is daunting to know where to start. But this is my pitch to make sure you travel to Cortona, Italy.
Here’s the tl;dr: Cortona is one of the best cities in Tuscany because of its stunning location, Renaissance art and architecture, relaxing atmosphere, and amazing local food and wine.
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The #1 Reason You Need to Visit Cortona
The stunning hilltop setting. Cortona is a hillside town where you can see some of the best views of the stunning Tuscany countryside. Sun-drenched fields littered with small towns as far as the eye can see await you in Cortona. You can even see nearby Lake Trasimeno.
These views become even more spectacular during golden hour and into the sunset hours. If watching the sun set over the Tuscany countryside with a bottle of wine is something you want to do before you die (and it should be) Cortona is the place to do it.
The hill the city sits atop is about 600 meters (1,970 feet for us Yanks) above sea level, so you can rest assured you’ll get your steps in, as the city also sprawls down the hillside. That means there’s a decent number of steps guaranteed if you’ll be visiting Cortona. Those with mobility issues may want to consider another Tuscany town. Those with no mobility issues and desire to eat endless pasta without gaining weight, scroll on.
The #2 Reason You Need to Visit Cortona
The medieval architecture. I’ll start by saying I know next to nothing about architecture. I barely know how to spell it on a good day. But if you’re like me, you will still absolutely love basking in the architecture of Cortona.
It’s not just medieval architecture, as Cortona dates back to the Etruscan times in Italy, the period of 900 to 27 BC (which is just a mind-bogglingly long time ago to me). Part of the massive stone walls encircling the city are still standing today, even more impressive considering how long ago they were first built.
The center of Cortona is medieval in nature. The streets are so narrow that I have no idea how anyone could get a car through them, and they wind and twist around the city like a maze. Multiple medieval towers loom over the winding streets. The terracotta roofs and tan stone facades make you feel transported back in time.
Not to mention the city of Cortona, much like many Tuscan towns, thrived during the Renaissance. There are several prominent buildings with clear Renaissance influence, like the Palazzo Comunale and Church of Santa Maria Nuova.
Reason #3 to Visit Cortona Italy
The FOOD. Let’s be honest, this is one of the main reasons people travel to Italy – for the otherworldly good food. The food we ate in Cortona specifically was some of the best we ate in Italy. The pasta we had in Cortona put the pasta we had in Rome to shame. Florence, who? Cinque Terre? Forget about it. Cortona is where it’s at.
The tiny hilltop town of Cortona is home to over 45 restaurants, 4 of them appearing in the Michelin guide. Not to be repetitive, but the wild boar pasta we had in Cortona was out of this world. And the tiramisu dished out of a large glass bowl? Felt like my Italian auntie cooked it for a big family meal (I am mostly Polish with no Italian auntie to speak of, much to my great regret).
The phone does not eat first in Cortona Italy.
If you’re traveling with kids, or if you’re like my husband and have a personal daily gelato quota while you’re in Italy (fine, it was my goal too), Cortona has got you covered. Multiple gelaterias are available to you for when you get a little too warm walking around the hilly, sun-soaked city. Snoopy Gelateria is my personal fave.
Besides the sweets and the many delicious seated dining opportunities, there are also plenty of opportunities to do activities in Cortona centered around delicious Tuscan food.
- This cooking class teaches you how to make pizzas, pastas, and focaccia, which you can enjoy on the estate’s terrace overlooking Tuscany once you’ve finished cooking.
- For those without any Italian family to speak of, this typical Tuscan dinner with a Cortonan family is available for booking.
- This wine tour and tasting is an unforgettable experience if you’re in Cortona, Italy. It is a boutique family-run winery, managed only by women with limited wines not produced for the mass market. The family has been making wines since 1625!
That last one brings us to #4…
The #4 Reason to Visit Cortona Italy
The wine! Cortona is a wine-producing town with varietal wines that are made from local and international grapes, the most important of them in the area being Syrah. The town has a long history of viticulture; archaeological digs discovered ceramics used for wine making and drinking dated into the BCs. The Etruscans who built that stone wall even trained vines to grow up tree trunks rather than along wires, those crafty Bs.
Any red wine you have is going to be particularly fantastic, as the growing region is best suited for reds. If you find yourself somewhere with a menu that has wild boar pasta, take it from this wine novice, it pairs phenomenally with the Syrah. The whites and rosés are also going to be delicious.
Look, I’m a Basic Economy B and I was definitely balling on a budget when I visited Cortona with only a few dollars to my name, and even the cheap wine in Tuscany is good. You can find bottles of wine for under $5 USD where the grapes were locally grown and the wines locally produced within 50 minutes of the city you’re in.
We bought a bottle of $2 local Rose in the afternoon, making sure it had a screw top instead of a cork. We took the bottle and found a quiet spot on a section of the low ancient stone walls and watched the sunset over Tuscany, passing the bottle between us. For $2, it was an experience I will never forget.
Cortona is one of the best cities to stay in Tuscany. Here are some excellent hotels to stay in Cortona:
- B & B San Francesco Charming and super affordable B & B, right in the heart of Old Town. Rooms available for under $100/night before taxes and fees.
- Hotel San Michele This is another great place to stay in Cortona. It is centrally located, with panoramic views of the Tuscany countryside. Slightly more expensive than the previous option, but great value in Italy.
- Monsastero di Cortona Hotel & Spa This is a boujee luxury option that would be especially great for a honeymoon or anniversary trip in Tuscany. The hotel is a historic monastery that dates back to the 15th century and was carefully renovated into a boutique hotel.
Reason #5 You Need to Visit Cortona
The Renaissance Art. For being a relatively small town, Cortona is a haven for its art and history. The Museo dell’Accademia Etrusca MAEC has a huge collection of art and artifacts from the 1000 BC. It houses one of Luca Signorelli’s tondos from the late 1400s. Tickets are €10, and opening hours are 10am-7pm from April through October and 10am-5pm in the winter months.
I don’t always love seeing artifacts outside of where they were found. I don’t find museums in London that intriguing because I question whether or not they’re the authority to be displaying items from Ancient Greece or Rome. But seeing Roman pieces on display on the very ground where Romans ruled? That’s cool stuff.
The Museo Diocesano isa converted church and is a must-see in Cortona as it proudly displays artworks from the 13th to 19th century. The Renaissance period is on full display with works available for viewing by famous artists such as Luca Signorelli (Lamentation over the Dead Christ) and Fra Angelico (The Annunciation), among others. It’s open 10:30am-6:30pm from April to October with reduced hours in the winter months. Tickets are €6 with an audio guide included.
Try to figure out the best month to visit Italy? Check out my guide to the best month to travel to Italy to help you plan.
Beside the museums and art galleries listed above, the town of Cortona has a handful of privately owned art galleries whose doors are open for tourists to wander into. Generally speaking, there are many charming stores found in the narrow, twisting streets where popping in is a perfectly pleasant experience.
Reason #6 You Need to Visit Cortona
The location. Besides its unforgettable hilltop setting, Cortona is one of the best cities to stay in Tuscany because it is conveniently located in the heart of the countryside and acts as a great homebase to explore more of the region.
The Camucia train station is about a 30 minute walk up or down hill. If that doesn’t sound like a good time to you, there are local buses that will take you into town, so no need for the nightmare of hauling your luggage around. The bus stop is right by the train station and takes you into the actual town. The school bus also picks up there and locals actually indiscriminately use both, so proceed with caution as the school is not all the way in the town.
Travel to Cortona Italy is easy, just a quick 90 minute direct train ride to and from Florence with trains about every hour. The ride itself is €8-12 depending on the time of day. If you’re staying in Florence, Cortona is an excellent city to day trip to. If your homebase is Cortona, you can enjoy the quiet of town and get a great night of sleep with little risk of tourists or locals keeping you up before heading into Florence for the day.
Arezzo is another one of the best small towns in Tuscany that both belongs on the cover of a travel book and is only 23 minutes away by train. With its close proximity to Cortona, the town has its own fortresses, museums, and castles that are well worth your time. The Arezzo Antiques Fair occurs the first Sunday of every month and the Saturday before if you happen to have your Italy trip scheduled over that time.
Otherwise, if you have a rental car, then Tuscany is your oyster (outside of the previously mentioned tiny roads). Montalcino is a 45 minute drive away and is known as one of the best towns for wines in Tuscany. Note: wineries in Italy are not like wineries in the U.S., so don’t expect Napa. You have to make reservations in advance, and very few allow walk-ins. Siena, Italy is an hour drive from Cortona and is also one of Italy’s loveliest medieval cities.
Reason #7 You Need to Visit Cortona Italy
The vibes. Cortona is one of the best towns in Tuscany to actually enjoy the atmosphere. I am always a huge fan of making sure you have at least 1-2 days built in any itinerary where you can move at a slower pace in between sightseeing and full days. Cortona is the perfect place to actually relax and unwind and enjoy a different pace of life.
If you’ve been going from Venice to Rome or Florence, you’ve surely spent a lot of time scooting around a lot of people, watching for pickpockets, and trying to take in everything you possibly can. Building in a day where your itinerary is lighter and you’re away from all the crowds and tourist destinations (which are still worth seeing!) can do wonders for making your trip actually feel like a vacation.
This can also be a really good budget way to travel too. If you’re filling your day with excursions and sightseeing activities, you’re emptying your wallet to do that. If you build in a lighter day where your goal is to enjoy the Tuscany countryside (and you know that good wine is cheaper than water), you save your sanity and a few dollars. Or euros, more accurately.
I also almost always find towns like Cortona worth staying the night. A town’s whole vibe changes when day tripping tourists leave. As evening falls on Cortona, you’ll feel more like a local than most other parts of Italy. You’ll feel like you’re in on a little secret with them when you finish your sunset bottle of wine and wander around through the even quieter narrow streets, hearing more Italian echo off the cobblestones than English, German, or Dutch.
Trying to blend in with the locals? Or at least distinguish yourself as someone who attempted to learn a few words of the language of the country you’re visiting? Download my free instant Italian phrasebook. It’s a one-pager you can screenshot to use in basic conversation with locals on those lovely evenings on the piazzas.
Want more?
Still planning your dream trip to Italy? Check out my 7-Day Italy Itinerary that includes room for a day spent in Cortona.
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