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10 Things To Do Under The Tuscan Sun-Cortona Italy

10 Things To Do Under The Tuscan Sun-Cortona Italy

This month I spend 2 glorious weeks in Italy. It’s my 4th time there. This time around my husband and I went alone without the kids. Its was one of our best vacations ever. Don’t get me wrong in the previous 3 trips to Italy, we had an amazing time. It’s surely taught us many things about Italy’s culture, how to navigated the train system and we explore the many beautiful cities. I discovered that Tuscany region is my favorite. Hope you enjoy this post 10 Things To Do Under The Tuscan Sun-Cortona Italy

Taking the Train To Cortona
Our first day in Italy we were picked up by our driver from  Leonardo da Vinci airport in Rome and taken to the train station called Tiburtina. There are two train terminals in Rome, Roma Termini and Tiburtina. Tiburtina was very easy to get around. We had train tickets to Cortona, Italy. This is my second time in Cortona.

Cortona is a beautiful town high up in the mountains. It has become a very popular destination in the last 15 years primarily due to the Frances Mayes book “Under The Tuscan Sun”. Frances lives there with her husband. The town is full of antiquities and beautiful landscapes. It’s easy to get to from Rome. We also visited the surrounding towns near Cortona such as Montepulciano and the beautiful Trasimeno Lake

Monastero di Cortona Hotel and Spa
We were picked up at the train station by another driver. It was a 30 minute car drive to Cortona. The ride was magnificent, small winding roads and views of beautiful medieval towns. We were greeted at our beautiful hotel with drinks and a tour. The hotel is a 14-century monastery that was converted into a boutique hotel. Everything inside the hotel was renovated. The kept all the stone in original condition, but the plumbing and electric were all brand new. The décor was just stunning. There was a beautiful plunge pool in the back of the hotel. The hotel had a gorgeous spa where both my husband and myself reserved a massage later that week. Its definitely a 4 star hotel and the rate was not.

Walking around the streets of Cortona.

One of the best things to do in Cortona is to walk the cobblestone streets. The streets are steep. Our hotel was the highest part of Cortona, so every night we got our exercise especially after our delicious dinner. The nights around Cortona are just beautiful you can see lights from the towns miles away. The food is to drool over, not a bad restaurant anywhere.


Shopping Around Cortona

There are lots of quaint stores with amazing linen products and leather goods. I purchased a bunch of lemon linen. I found this one store that sold coffee sacks made into pocket book products.  It gave me an great idea for my next project since I have tons of coffee sacks.

Day 2: Biking through the Farms of Cortona Region

The next day we were picked up by our bike guide Sergio. He was an excellent guide. Took us through the grape vineyards and sunflower fields. It was a dream come true for both my husband and I. We loved every minute of it.

Visiting  Winery in Montepulciano Italy

Our bike guide had planned a  tour of one of the  winery in Montepulciano, which is the next town from Cortona. Two ladies run the winery. They produced 30,000 bottles a year, so its a pretty successful small winery in the region. The wine is so good they use very little sulfates. They gave us a tour of the winery and later had a nice lunch which they served several different wines. I stopped after two tastes since I had to ride my bike back. The house was beautiful. Big green shutters and the grounds were breathtaking.

Day 3: Played tennis in Cortona On Red Clay

Italy is known for there red clay. Both My husband and I play tennis regularly. So we bought out tennis racquets. We knew that Cortona and Capri  both have nice tennis center. We spent the morning waking to the tennis center. Stopped along the way to several museums. The walk was beautiful you can see the mountains all around the town. There are cliffs everywhere which you can see for miles. Tennis was a bit hard since the elevation is high so we tired easy. It was a great work out. We walked back to our hotel to have lunch and later that day we both had our massages at the spa. It was a great way to relax.

Day 4: E Biking around Lake Lake Trasimeno
Our last day Sergio had another bike tour planned for us. He was taking us to explore more of the Cortona region and lake Trasimeno. The lake is only 10 miles away from our hotel. There we saw lots of beautiful views of the lake. I rented an Ebike. E-bikes are amazing because they give you an extra booth going up the winding roads. You still have to peddle but the extra juice was much needed. The roads had light traffic. I had to giggle because both my husband and the guide had regular road bikes. I asked my husband if he wanted an e-bike and said no. Both of us are avid bikers, but I knew I would need the E-bike since I am not used to theses hills.

We stopped at the lake, had some lunch at a cute town called Castiglione del Lago. The town has some old churches and lots of  historic buildings. There is a medieval fortress  that surrounds the town to protect from intruders in the 15th century.

Its our last day in Cortona. I could have stayed longer in this region. The people are very friendly and you feel at home. Next Stop Capri. Italy. I hoped you enjoyed 10 Things To Do Under The Tuscan Sun-Cortona Italy.  (For more Italy trips and tips ideas check out travel stress free to Italy)

(This is a sponsored post as well as there are some affiliate link on this post which I make a small commission. )



  1. What a beautiful place. I lived in Italy for a few months and never read about this place and it looks wonderful.

  2. Donna Shoaf says:

    Beautiful, very helpful guide to this area!

  3. Wow! It looks like you had an amazing trip! The photos are stunning! The vineyard looked incredible. Under The Tuscan Sun is one if my favorite movies. ?

  4. How beautiful. We just spent 2 weeks in Switzerland and Italy, a week in each. So beautiful. I’m working on a series of posts now, hoping I get them done at some point. Lol. Love reading about your visit and this region, I’d love to visit again.

    1. Switzerland is very close to Italy so that great you got to see both. Hope to read about your trips.

  5. What a great trip, Maria! It must have been so much fun to bicycle around the area… The scenery is beautiful! Reminds me a lot of California… Happily shared several photos as I read my way through the post. <3

    Happy fall to you,
    Barb 🙂

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