Traveling Under the Tuscan Sun | Cortona, Italy

The first thing that I MUST point out, this is the first place I have ever visited where I can honestly say, the pictures and videos do not do it justice. The Italian Tuscan region, particularly Cortona, Italy, is absolutely breathtaking. In this post, I am sharing some of our favorite activities, food, and accommodations for the area, as well as some heartfelt stories and experiences that I will NEVER forget. I cannot imagine having lived my whole life without experiencing the beauties of Italy!

While all opinions and reviews are my own, this post is sponsored by Discover Cars.

Be ready to experience absolute relaxation, beauty, and awe during your stay in Tuscany. I have been to many spas and slow-paced beach resorts in my travels, but nothing has given me the sense of peace and tranquility that the Tuscan countryside provides, especially the views of Borgo di Vagli, our little hamlet nestled in an olive grove high above the Tuscan valley.

Where to Stay in Cortona | Borgo di Vagli

After over five days of driving all over the Cortona mountainside, visiting all the nooks and crannies of this medieval town, I am 100% confident in saying, Borgo di Vagli is THE place to stay if you want the most magical experience that Cortona has to offer when it comes to Cortona Hotels. Remember earlier when I said, the pictures don’t do it justice? You have to imagine it being even more beautiful than the images below.

Borgo di Vagli is a Tuscan hamlet that dates back to the 14th century, but its “bones” originate from the 10th century. How is that so? This hamlet used to be a watch tower for the Castle of Pierle which can be seen on a clear sunny morning off the right of Borgo di Vagli. (image below) After the watchtower was no longer useful in the 14th century, the keepers of the watchtower recycled the stones and rebuilt around the watchtower base to create the hamlet that you see today.

I took these images right from the porch of our Borgo di Vagli apartment. As you can see, depending on the weather God decides to grace you with, you may get a completely different experience of the view each morning. Sometimes we woke up to a bright, dewy morning with the birds singing their songs as the sun rose over the mountain, and other times the mood was much more somber, but in the most beautifully peaceful way possible with fog soaking the valley and the morning call of a swift passing by.

Borgo di Vagli is a privately managed Tuscan hamlet that has been restored by award-winning restoration architect Fulvio Di Rosa. Before arriving to Borgo di Vagli, I did my research and learned all about Mr. Fulvio’ s vision and how he brought his idea for Borgo di Vagli to fruition, but I could have never dreamed that I would actually get to meet this brilliant man! (image below) Little did I know, he comes up to Borgo di Vagli every Monday for pizza night and converses with the guests while enjoying dinner at Borgo di Vagli’s restaurant, I’cche c’è c’è.

I have to admit, I “fan-girled” like I had just met the Pope, or maybe even Brad Pitt, and asked for a picture. Having dinner with Mr. Fulvio was so inspiring. The man is brilliant, with huge ideas that he never fails to execute with precise perfection and the Borgo di Vagli experience is just one confirmation of his genius. I left dinner that evening feeling so inspired, like I could accomplish anything if I just keep trenching forward to reach my goals.

But Mr. Fulvio wasn’t the only person we met at Borgo di Vagli. It has been published that, I’cche c’è c’è, Borgo di Vagli’s restaurant, offers “dishes that only old fashioned housewives are capable of preparing nowadays.” Around 5 PM in the evening, you can smell the firing up of the grill in preparation for a nightly feast, which brings all of the guests down to dine together, sharing not only stories, but one of the greatest gift humanity has to offer, the sharing of time, and “life-in-general,” with one another.

Can you believe we met a couple from Norway, Elsa and Harold, who actually went to college in Little Rock, Arkansas, just shy of two hours from where we live in Memphis? They have spent many summers and winters at Borgo di Vagli. We just loved hearing them reminisce about all of their adventures. It’s little things like these that make you feel validation that we were in the right place, at the right time in that moment in Tuscany. We also met a lovely couple on their honeymoon from California and a mother daughter duo exploring together from Pennsylvania.

Every evening, owners and guests of Borgo di Vagli come to I’cche c’è c’è to enjoy Chef Dina and her daughter’s, homemade Tuscan cooking, using only a wood-fired grill and ingredients sourced daily from both the property of Borgo di Vagli and the town of Cortona.

If you would prefer an intimate dinner in your apartment, the amazing staff at Borgo di Vagli can arrange that as well. Stefania, Azzurra, and the rest of the amazing staff can arrange in room dinners, excursions, wine tours, and dining reservations in the city to make your experience extra special. Upon arrival to Borgo di Vagli from Rome, it was quite late so we called ahead of time to have dinner, wine, and dessert delivered to our apartment. It was such a warm welcome coming off of a tiring 2.5 hour journey from Rome.

Speaking of our room, we immediately felt like we stepped back in time upon entering our apartment. The wooden trunk ceiling beams, stone window openings, antique shutters, and authentic copper cooking pots, brought a feel from the medieval times while the fridge, oven, and stove masked with wooden door panels helped to furnish the space with modern amenities while not straying from the medieval design era.

If you prefer trying your hand at a little Italian cooking, there is a market on site that sources local produce, pasta, sauces, wine, and beer. Mr. Greg picked up some ingredients and cooked a delicious meal for us for our last night. I have to admit. It was in my top three favorite meals while in Italy, and not only because it was made with love, but because he is quite the cook!

Ok, I have to move on from Borgo di Vagli because the tears are beginning to flow as I write. I just can’t describe the appreciation I have for my time at Borgo di Vagli. All of the troubles of our life back home seemed to melt away, and nothing else mattered for the moment.

Travel Through Tuscany

When you visit Tuscany, you definitely need to rent a car. In the major Italian cities, you could get around by bus or train, but if you are to spend any amount of time in Tuscany enjoying the country side, I highly recommend renting a car from Discover Cars. Not only do they have a very large selection, but they are very reliable and affordable. For only $150 euro, we were able to rent a car straight from the airport for 9 days, insurance included! You can’t beat that!

What is Cortona Known For?

Cortona is a town in the Tuscany region of Italy originally founded by the Etruscans, and still holds on to many of its original remains from the Etruscan period. It is known for its rich history, art, and picturesque surroundings.

What is Cortona is known for:

Historical Significance: Cortona has a long history dating back to Etruscan and Roman times. The town has well-preserved historical architecture, including medieval and Renaissance buildings, walls, and fortifications.

Art and Culture: Cortona is home to several churches, museums, and art galleries. One of the most notable is the Diocesan Museum, which houses important works of art from various periods.

Santa Margherita Sanctuary: This sanctuary is situated on a hill overlooking Cortona and provides panoramic views of the surrounding countryside. It’s a popular spot for both religious pilgrims and tourists.

Etruscan Academy Museum of the City of Cortona (MAEC): The MAEC museum showcases artifacts from the Etruscan civilization, providing insights into the pre-Roman history of the region.

Cuisine and Wine: Like many places in Tuscany, Cortona offers delicious Italian cuisine and local wines. Visitors can enjoy traditional Tuscan dishes in the town’s restaurants and explore the local wine scene.

Cultural Events: Cortona hosts various cultural events and festivals throughout the year. These events often celebrate the town’s history, art, and traditions. There is an authentic Italian market in Cortona the third Saturday of each month where you will find antiques, local produce, and other local goods. 

The Cortona On The Move Photography Festival: This annual event attracts photographers and photography enthusiasts from around the world. It features exhibitions, workshops, and discussions on contemporary photography.

The Bramasole: The town gained additional fame through Frances Mayes’ best-selling memoir, “Under the Tuscan Sun,” which recounts her experiences restoring a villa named Bramasole near Cortona.

Local Designers: Being a small business owner myself, I wanted to support local when it came to shopping, so I set out on a journey to find a one of a kind local, Italian leather bag to add to my collection. The first shop we visited in the square of Cortona was Laura Laureto. I was thrilled to learn that the kind woman that helped me find the perfect Italian leather accessory was Laura Laureto herself! 

I had so much fun spending time with her, learning all about the inspiration, intricate details and hand-work that go into her designs. I not only fell in love with pieces, but the familiar passion behind her stories as she told them and instantly knew that I couldn’t leave Italy without a Laura Laureto piece. Even Mr. Greg wanted a Laura Laureto, hand-designed, silk pocket square to wear with his suits. We throughly enjoyed our time in Laura’s shop and hope to visit again one day. 

Laura’s story behind the Leather Bread Bag Clutch that I purchased.
When Laura was a girl, her mother gave her a brown paper bread bag to carry, not just her lunch, but all of her things. She said is was like her first purse. When she began her journey as a designer, the leather, “bread bag” clutch was one of her first, and more well-known designs. I loved how one of her first designs tied back to her childhood. There was such a familiar feeling while she told her story as many of my childhood experiences too have inspired me as a business owner later in life. Not only had I made a fast friend, I felt an instant connection to her brand!

Cortona’s combination of historical charm, cultural richness, and scenic beauty makes it a popular destination for tourists seeking an authentic Italian experience.

Cortona Restaurants & Experiences

There is no shortage of restaurants in Cortona. Due to lack of time, we simply could not visit them all, but here is a little review of the few we did get to try, including a vineyard which offers a tour, wine tasting, and lunch experience. 

Nessun Dorma Restaurant

We just so happened to stumble upon this restaurant while strolling through Cortona with no idea that the dinner experience would take place underground in an old medieval stable. At first I thought the dining room may be an old wine cellar but the two large rings hanging from the ceiling looked to be horse ties, which then lead me to believe that we were dining in an old stable. Either way, it was pretty magnificent.

Being that Nessun Dorma was our first ever Tuscan restaurant, we both agreed that the appetizer of choice would be the full Tuscan antipasti sampler. This board was an explosion of flavorful goodness with every bite. I chose lamb and spinach for my main dish and Mr. Greg went with a Boar Capallini dish. Both the food and the atmosphere at Nessun Dorma was superb. Definitely the perfect introduction to what would be the beginning of our Italian food tour.  

La Dispensia del Preludio

While we didn’t actually eat here but we did order a glass of vino from La Dispensia del Preludio’s wine window as an after dinner treat to further enjoy our stroll through Cortona into the evening.

We had no idea that you could enjoy wine while walking in public but apparently in Italy, it’s a normal thing. If you are a wine lover, you should take the opportunity to enjoy all of the local labels Tuscany has to offer. They even have different wines for different stages in the dinner process. Simply, ask your server what the local label is for the area and enjoy a new wine experience each time. At La Dispensia, we did just that. Since we had just finished dinner, we requested a post-dinner, local wine and they definitely did not disappoint.

La Loggetta

The  was my absolute favorite dining experience within the city walls of Cortona. La Loggetta is more on the fine dining side making it the perfect spot for an upscale dinner date and for trying dishes known exclusively to the Cortona area. For our antipasti (appetizer) we tried Zucchini Flowers dipped in an olive oil pesto base. This was a first for us! We were both pleasantly surprised with the flavor and I instantly deemed Zucchini Flower my favorite appetizer in Cortona. 

We also enjoyed a side of fried artichokes with our main dishes. Greg had piglet and mushrooms while I opted for the dry aged beef. Of course, a cannolo (canoli) isn’t truly Italian unless it is made in Italy so I went with the cannolo con cheese cake e frutti rossi while Mr. Greg tried the Crème Brûlée and nuts. We definitely shared in the end. 

La Braccessca Winery Experience

It wouldn’t be the FULL Tuscan experience without trying one of the many Tuscan Wineries. The incredible staff at Borgo di Vagli recommended and booked the La Braccessca Wine Experience for us. So on our last day, after enjoying my last morning cup of coffee while soaking in the morning view of Pierle Castle, we cruised through the Tuscan Valley with our windows down and the sunshine on our face. 

With over 1000 acres of vineyard, the initial view upon entering La Braccessca was majestic. After we toured the vineyard and cellar, we got the pleasure of enjoying a private wine tasting for two. We both had a lot of fun trying to identify the notes in each wine that we sampled and even brought home three of our favorites to enjoy at our upcoming Friendsgiving next week and at our traditional Christmas dinner that Mr. Greg and I have with just us and the boys. 

After our tasting, we were served a delicious lunch. I was shocked that they offered Tuscan delicacies that I haven’t yet tried. I thought I had tried it all by now! The lunch was fantastic and overall experience a must!

Now, answering a few questions that you all had for me.

Is Tuscany closer to Florence or Rome?

Technically, Florence is a part of Tuscany, however most people refer to the Tuscan countryside when they refer to Tuscany. We stayed in Cortona which is about 2 hours from Florence and 2.5 hours from Rome. The Tuscan countryside is pretty much the region in between Rome and Florence.

What food is Tuscany famous for?

  • Tuscan black croutons
  • Colonnata Lard.
  • Panzanella.
  • Pappa al pomodoro.
  • Ribollita.
  • Cacciucco.
  • Tripe and lampredotto.
  • Bistecca alla Fiorentina (Fiorentina steak)

Do I need a car in Tuscany?

The are 10 provinces that make up Tuscany, each rich in history and their own culture. You will want to see them all. Due to Tuscany’s mountainous region, I would highly recommend renting a car so you can enjoy a ride through the beautiful Tuscan mountainside and valley to visit all of the medieval villages.

My Heartfelt Message

While I know this post is quite long, I wanted to take the time to share our full experience for anyone hoping to travel to Tuscany. Even though it was our first time here and we didn’t have a lot preplanned, I felt like we were divinely lead throughout our journey. The meeting of strangers, who we can now call friends, every eatery and shop we stumbled upon, even the rare clearing of trees along the roadway that provided a quick glimpse of God’s magical creation, all provided a strange sense of clarity that no matter the hardships in our lives, God has a plan, as long as we follow him.

I hope that one day you too get to experience it all. I said it over and over while I was there, I said it at the beginning of this post, and I will say it again, “I cannot imagine having lived my whole life without experiencing the beauties of Italy!”

Ciao Ciao

Adventure Blooper Moment: We unknowingly played “Siri Said So.” I do not recommend.
We drove down a flight of stairs in Cortona because .. well… Siri said so! Note to self, Siri isn’t the best at navigating Italy. More on that later when I share our visit to Florence! Haha

Hi! I'm Alexandra

I am an entrepreneur, author, and mom of 3 from Memphis, Tennessee. I fill my days pursuing the dream of being my own boss as a full time influencer and sensory marketing specialist while spending my evenings playing superheros, helping with homework, making dinner, and tucking in my littles.

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