Mar 16, 20238 min read

5 Days in Cortona, Italy

Updated: May 18, 2023

Visiting Cortona was a dream! My family and I visited Cortona in December of 2022 over the holidays. We decided to go here because it was well-established, yet smaller and less touristy than other hill-top Tuscan towns. The pace of life in Tuscany is slow and relaxing, so get ready to kickback, eat lots of food and indulge in amazing wine! What could be better?

In Tuscany, I have also been to Montepulciano, which is similar but slightly bigger and more visited. I have also spent two nights in Pienza and it has a very similar relaxing pace to Cortona. You really can't go wrong with Tuscany in general, as the food and views won't disappoint. The food was incredible, the locals were welcoming and the prices were very reasonable. I had some of my favorite meals in Italy here!

How To Get There

Given that it is the Tuscan countryside, you will need to fly into a major airport, such as Rome or Florence, and drive from there. We flew into Florence, rented a car, and drove to Cortona. It is a fairly easy and an extremely stunning drive. It is only an hour and a half drive that flies by with the gorgeous views. There is also the option to hire a driver or shuttle if you don't feel comfortable renting a car. I would highly recommend renting a car because there are very few taxis in Cortona as well as the rest of the countryside. Having the access to your own car gives you endless opportunities and access to the surrounding area.

When To Go

You can really visit Cortona all year round! In the winter there are beautiful Christmas lights and markets, along with a smaller crowd. In the summer, it is very warm so you can enjoy the sunshine and experience an Italian summer full of wine tasting.

Where To Stay

Like I mentioned, Cortona is not a huge town with minimal tourists, thus hotels are limited. There are plenty of VRBO and AirBnb options! With Tuscan hill-top towns in general, you can either stay outside the walls, where you will find more villas with pools and land, or within the walls, which tend to be more flats yet walking distance to restaurants and shopping.

With our family we like to stay inside the walls so we don't have to drive much and can all explore freely. If I were to visit in the summer, I would consider staying outside the walls to opt in for a pool!

The VRBO we stayed at was amazing. The host was super communicative, it had such a fun historic and charming feel as well as amazing window views of the countryside . It was reasonably priced and I would highly recommend this place if you get the chance to visit! We were a very short walk to all the local boutiques and restaurants which really helped us immerse into the Italian culture. This VRBO had plenty of space for 5-6 guests. There is also a free parking lot nearby if you drive to Cortona in a rental car.

Itinerary

Day 1: December 24

After flying into Florence and getting our rental car, we made the 1.5 hour drive to Cortona! It was a gorgeous, scenic drive with amazing views of the rolling green countryside.
Once we were checked into our VRBO, we grabbed charcuterie and wine at a nearby wine bar. It was a modest and no-frills venue, but the cheese selection was amazing. It was a great stop for a quick and casual snack.
My mom, sister and I enjoyed shopping down the main street. There were a few great clothing boutiques with reasonable prices as well as little shops that were great for souvenirs.
We had dinner at Bucaccia at 7pm. This is a MUST visit. It is a Michelin star restaurant, and it did not disappoint. Make sure to have a reservation because it has very few tables. The owner personally greeted and checked in on us, and the rest of the staff was lovely. It was the best Christmas Eve dinner ever! Even for being a Michelin Star, it was very reasonably priced compared to American dining out standards. Pastas were about 15 euro and steak about 20 euro, with no necessary tip after your meal. We still reminisce about this meal and it is a must on your trip to Cortona.
During this time of year, there are beautiful Christmas lights as well as a light show projected in the main square. We walked around after dinner to enjoy the festive decor!

Day 2: December 25

Spending Christmas day in Cortona was incredible! To our surprise, a lot more restaurants and shops were open than I had anticipated. The town was bustling and the mini Christmas market, that included various pop-up shops of trinkets and clothes, was open as well. There was plenty to do and see, even for a holiday! We were blessed with amazing blue skies and sunny weather. Even in the winter, the weather tends to be pretty mild.

We started our day with a classic Italian cappuccino at Caffe Bar Signorelli. This cafe is close to the main square which makes it great for people watching. You will also find a lot of locals here and we even made some friends who we continued to see throughout the rest of our stay as well! The pastries and flatbreads were also delicious if you are seeking a snack.
Knowing it would be open on Christmas, we made the walk (or hike rather; it is very steep) up the hill to the Church of Santa Margherita. It is a gorgeous and colorful church with amazing views since it sits at the highest point of Cortona. I truly believe the church is well worth the walk, and going inside is free.
Luckily for us, Baracchi was open for lunch on Christmas day and we had a fabulous meal here. Baracchi is a winery outside of town, but they have a restaurant and wine bar in town. It had a modern twist on Italian food, making it a good break from the usual pizza and pasta. I had an amazing salmon and split a pasta with my mom. It is a family-run winery/restaurant and we had a long chat with one of the daughters. She informed us they also offer cooking classes and lovely wine tasting at the location outside of town. Unfortunately, we weren't able to make it there but, I would definitely put it on my list if we had the chance again!
The rest of our afternoon was very mellow, just spending time together, reading books, wandering the town and sharing lots of wine.
To finish up a relaxing yet incredible Christmas, we had dinner at La Logetta. This restaurant is right off the main square and was another incredible meal! The Cheese fondue with truffle, pici pasta with black pepper and truffle, and the seabass were to die for. Pici and fagioli are Tuscan local dishes, and never disappoint! I like to try them everywhere I can. The restaurant had a cute interior with great space for larger groups. The staff was attentive, the food was reasonable and we left happy!

Day 3: December 26

Unexpectedly there was a flea market in town this day! My sister and I love thrift shopping, so we spent hours looking through all the stands and picking up cool items. They had everything from old postcards with hand written letters, old black and white pictures of Italy, to vintage clothes and film cameras. It was so fun to talk to the vendors and get some super unique souvenirs for a great price
We went back to our favorite cafe, Caffe Bar Signorelli, for lunch! They served traditional pasta dishes that felt like they were made in grandma's kitchen. The meal was very cheap (7-8 euros per dish) and super delicious! I would recommend the food if you are looking for a casual and quick lunch.
For dinner, we dined at Taverna Il Gozzoviglio. This is a cute 8 table restaurant with a mom and pop feel. The food was traditional, hardy and extremely delicious. I enjoyed the tuscan bean soup and a bolognese. We all felt that this was a great spot for a casual family-style dinner. Although it was nothing fancy, this is still one of my favorite meals!
To end the night we had a nightcap at Bar il Solco, which was right across the street from dinner. The owner was DJing fun, upbeat music, so we couldn't resist! This is one of the few bars in town, so you really can’t miss it. Drinks were 5-7 euros and the ambiance was so fun. This is a great spot to go have some drinks and chit-chat. Not to mention I loved the logo and the owner gave us some cool stickers as a souvenir. I still see mine on my water bottle everyday, and it always makes me reminisce!

Day 4: December 27

This was the busiest day of our Cortona trip, but one of the most fun! We did a day trip to Montepulciano and Pienza with our rental car.

One of our favorite wines we discovered on our last Montepulciano trip was from Dei. We decided we had to visit the winery itself on this trip. We left around 1:45 for a 2:30 wine tasting tour. The winery is in Montepulciano and only a 35 min drive! The road is a bit windy, but has amazing views on the way there! Make sure to book ahead and have your winery reservation in advance through their website. The property was gorgeous and modern with very artistic architecture. We were really fortunate to be the only 5 people there and have a completely private tour! This is one of the main perks of traveling in the off-season.The tasting itself was delicious and only 20 euros! We got to see all of the grounds, the cellar and the wine making process followed by the tasting accompanied with some light snacks. Overall it was a lovely experience and I would go back again!
After some wine we were a little hungry, so we stopped in our favorite town of Montepulciano for some charcuterie. I wish we had more time in Montepulciano. If I were to do it again I would have gone before our tasting, especially if you haven't been to Montepulciano before, it is a great place to spend an afternoon.
One of our favorite things on our trip was our cooking class at Podere Il Casale. Our cooking class was at 5:30 pm and about 5 hours long, but it flew by! Food is super important in my family, so I wanted to find an intimate cooking class with high quality food. I did a lot of internet digging to find this place, but it was well worth it. Everything we consumed was grown on the farm, so it was truly a farm-to-table experience! We were the only 5 people in the class and the instructor was the owner of the farm. She was so sweet, knowledgeable and fun to spend time with. While our food cooked we got to explore some of the farm and see all the sheep, 14 dogs, lots of cats, and we even walked by there cheese making barn. After preparing our fantastic 3 course meal in their kitchen, we got to sit down and enjoy it in a nice ambiance at their restaurant. They plated our food for us and made it look fantastic, and tasted even better! I would do this experience again in a heartbeat.

Day 5: December 28

On our final morning in Cortona, I went for a lovely walk up the hill, did one last look at the shopping and got my final cappuccino before hitting the road. Our next stop was Florence, so we had a short 2 hours back to the city!