Under the Cortona Sun: Day Trip
- tingletravels
- Jan 8
- 4 min read
Updated: Jan 9

A quick breakfast and we are off! But take it lightly, we are about to make and eat A LOT of cheese. This day will take us through Val di Chiana, with Cortona as our main focus. Cortona is a gem of a town, perched on the edges of a vast hill side, overlooking the Val di Chiana. The town is most famously known for its role and setting in the early 2000’s Rom-Com, Under the Tuscan Sun. If you want to catapult yourself out of the van and buy a villa somewhere, we get it.

First stop, Fattoria Bistecca. We know you have been eating a lot of cheese, but you haven’t made it yet. The staff at Fattoria Bistecca will guide us through a 3-hour experience of making three different kinds of cheeses; raveggiolo, pecorino, and ricotta. Fattoria Bistecca will train us through the traditional method of production and aging, using raw milk. The experience will be accompanied by bruschetta, pasta, pecorino, ricotta, and of course, wine. Keep your hands dirty and get to work, our cameras will make sure to document it for you.

Next, a few minutes down the road to our next winery. It might not feel like you can do it at first, but you can, you’re Tuscan now. We will spend a beautiful and light afternoon with Elisa and Luca of Iviti. We will learn everything organic as Iviti specializes in natural techniques in the field and production. They use some very rare and difficult techniques in both the vineyard and cellar that are hard to find elsewhere. Even though there has been a big shift in the wine industry with climate change, Elisa and Luca seem to have adapted to all of the ever changing factors quite nicely. This young husband and wife duo just celebrated their 10th vintage and are starting to take the area by storm.
This area of Tuscany doesn’t revolve around the classic and rustic Sangiovese as most zones, rather more internationally famed varieties like Cabernet Sauvignon and especially, Syrah. Cortona continues to become more and more internationally recognized for its high quality production of the finicky Syrah. The bold wines of this area are making a massive push as some of the best in Tuscany.

After Elisa and Luca guide us through their land, cellar, and introduce us to their lovely farm animals, (Virus the Goat will surely give you a good laugh), we will relax for a tranquil, but powerful tasting. We love it when a label has a good story to tell, and Iviti definitely displays some of the more unique designs around. A tasting with Iviti is always diverse as their lineup of wines offer an entirely different sip from each bottle. Their white blend is the perfect accompaniment to a hot summer day or fresh seafood. The Syrah, beautifully unoaked, packs a juicy punch that is great drinking for both warm and cold weather. The Cabernet Sauvignon has a lot to say, and can stand up to anything from Napa, while the Cabernet Franc is just as elegant and powerful as one you would find in the Loire Valley of France.
Iviti is definitely a hidden gem of Tuscany, and we couldn’t be luckier than having them as part of our team!

After the tasting, we will make our way up to the town of Cortona for some free time to walk around the rustic streets and enjoy the panoramic views of Val di Chiana.
We know, you’re stuffed again, but you have some time to recover before a big, rustic farm dinner. We will ride about 30 minutes to our last accommodation of the trip, tucked away nicely, just below Montepulciano. Sabrina will be waiting to check us in at Agriturismo Pescaia where you will have some time to relax before we make our way out to dinner, only a minute or two down the road.
The view and natural sounds here are priceless during golden hour. You can walk up the hill into town if you’re feeling adventurous, but don’t worry, we will spending the day in Montepulciano tomorrow. Take some time to rest and gear up for a big dinner of comfort food!

Around 7:30 pm, we will make our way down the road to Ristorante L’Oliveto, another family run Agriturismo in the area. L'Oliveto specializes in local ingredients and specialty dishes in this extremely cozy and rustic setting. If the weather is nice, we can sit outside amongst their olive groves, enjoying a glass while gazing upon the crystal clear, starry skies. If mother nature isn’t happy, don't worry, the inside echoing sounds of the crackling fire as Bistecca and Cinghiale roast for hours, prepping to be on your plate, is just as good. An incredible dinner to end another incredible day.
This day trip is part of our Grand Tour, and Nobile Wines, Organic Vines, and Val d'Orcia's Quintessential Taste, and "Dalla Botte" Tuscan Wine Club adventures. To learn more about these tours, click below!

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