Beautiful Tuscany: Cortona Village & Villa Loggio Winery

Beautiful Tuscany: Cortona Village & Villa Loggio Winery

Last July my family and I, along with my sister-in-law and her family, took a trip to Italy for ten days. We first stayed in Venice for three days, and then rented a villa in Tuscany for the remaining week. Anyone looking for a European family escape, and prefer to stay in one location for most of the time, Tuscany is the place to go. With endless day trips to choose from, excellent food for everyone, and a natural unparalleled beauty, it is the ultimate back-drop of adventure and fun for the whole family. 

The villa we stayed at (rented through Emma Villas) was in South Eastern Tuscany, outside the beautiful village of Cortona. Equipped with pool and hammock, set atop a hill with views of the country land and sunflower fields, it was beyond any of our expectations. The kids, naturally, went nuts. We pretty much panned our days like this: wake up, eat breakfast, leave for day trip, come back by 4 or 5, pool side for a couple of hours, eat dinner, let the kids pool it up some more, and watch the lights of Cortona light up while sipping on Tuscan wine. No day was the same as far as day trips were concerned, but every day we made sure to wind up the same, just like that.

Taking a walk in the countryside of Cortona, Tuscany.

The villages and cities we visited included Cortona, Siena, Florence, Montepulciano and the lovely Villa Loggio winery in the outskirts of Cortona. This post will cover Cortona and Villa Loggio.

Cortona was the first place we decided to visit, since it was our villa’s “home” town. A pretty, hillside town with cobblestone streets, it is best known as the setting for the book and movie Under the Tuscan Sun (it is also the chosen place for many Hollywood directors because of its lack of crowds and out of the way location). Driving up the hill to get there, every so often we would catch snippets of breathtaking views of both countryside and nearby Lake Trasimeno, and I knew before we got there I was going to love it.

We came across a stone medieval archway that appeared to be the “gateway” to Cortona, so we pulled over, parked and walked through. Indeed, it was like walking into a fairytale. One of the oldest towns in Italy, it looks exactly that. Narrow, winding streets that curve around until they reach a piazza or pretty vista, it breathes history and charm. It is small and quaint, and totally walkable. Perfect for a day trip with kids, it is off the beaten path and as I mentioned earlier, hardly with any crowds.

Walking in the cobblestone streets of Cortona, Tuscany.

Cortona’s main square is called Piazza della Republica, with another square nearby called Piazza Signorelli. Both are filled with quaint little shops, as well as fashion stores and restaurants, and fun to mill about.

For lunch we went to the lovely Osteria del Teatro, a restaurant in a pretty setting with flowers all around. The food was delicious: the ricotta filled zucchini blossoms in a broccoli puree were beyond, and the beef Carpaccio and the eggplant and tomato ratatouille amazing as well. My girls’ desserts were heavenly, especially their signature tiramisu, or “chocolate volcano”. The great thing about the restaurant was that they completely catered to the kids. As soon as we sat down, they came over with kids books and toys, all in Italian, which was fun for the girls. They seemed to be all about the kids there, despite the fairly sophisticated setting.

Delicious squash blossoms for lunch in Cortona, Tuscany.

After lunch we wandered around some more to work off the meal, stumbling upon art spaces, a photography show in an old hospital, and more boutiques and bakeries. We were making our way up and down streets, but eventually up, to where we came upon a few small churches and then a playground set in a park that overlooked the lake. Sitting in the bench next to the merry-go-round where the girls were playing, looking out over the valley and water, everyone was as content as could be. We hung out there for while, enjoying the peacefulness as if we lived there.

Looking out on the countryside from the hilltop in Cortona, Tuscany.

Also nearby our villa was the stunningly picturesque Villa Loggio winery. It was a bit of a random choice, as some of the other wineries we wanted to go to were booked for the day, yet a blessing in disguise as this was one of the highlights of our trip. Owned by a very friendly German couple, we were welcomed immediately, along with their two children, and given a tour of the grounds.

Driving up to Villa Loggia winery in Cortona, Tuscany.

In addition to the winery, they also own a hotel there, a beautiful old estate that dates back to the seventh century, which they have completely modernized. A true oasis, the property is perched up on the Chiana valley, with views of wine fields and olive groves in the near and far distance. Before our wine tasting was to begin, they asked us if our kids (we were also with my sister-in-law’s two kids) wanted to play in a separate room with their two boys, so we could get the full experience. It couldn’t have been a more ideal set up.

Chilling poolside at Villa Loggia winery in Cortona Tuscany.

We tried a variety of wines in a comfy, sun-filled room, and without asking they brought us platefuls of the most delicious Italian appetizers – cheeses, meats, figs, bruschetta, pizzettes, fruits. It was such a pleasant afternoon – with the kids playing in the nearby playroom – that we probably completely overstayed our welcome. But we could tell the owners were enjoying it as much as we were – as were their boys – and the afternoon slowly turned into dusk. They gave us a tour of the behind the scenes working of the winery, and when the sweet liquor, or digestive, rolled around, it was about time to go soon after. They were the nicest people and I just want to give a special shout out to them – if you and your family are ever in the area, it is a must visit.

Breathtaking Tuscan countryside in Cortona.

In general, the area of Cortona is a wonderful part of Tuscany to visit – it is what you see in the movies, and a great and easy place to take your kids on a family vacation.

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Cortona, Tuscany si a beatutiful and off the beaten path town in the Tuscan hills.

Linking up with Wandermust Family and the monthly link #fearlessfamtrav



  1. April 3, 2017 / 2:45 pm

    Tuscany looks like a beautiful place to explore. We have only been to a few places in Italy so definitely need to go explore some more! #fearlessfamtrav

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