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  • Writer's pictureGary Rosado

Italian Road-trip

Updated: Mar 10

If there's one thing that gets me excited, it's the thought of traveling to a new place. And this time, I had set my sights on Italy for a much-needed break from the daily grind. As someone who has visited Italy before, I knew that there was always something new to discover in this beautiful country. So, I decided to revisit some of my favorite cities and explore new ones for the next 21 days.

Our journey began in Venice, where we landed and picked up our rental car - a bright red Fiat 500 that screamed "Italian charm". The plan was to drive to the outskirts of Florence, where we had booked a room at the beautiful Hotel 500 Firenze for the night. As we drove through the winding roads, we were welcomed by breathtaking views of the Tuscan countryside.

As we arrived at the hotel, we were in awe of its grandeur and beauty. The hotel was a blend of classic and modern styles, and the spacious rooms were a sight to behold. After checking in, we decided to explore the hotel's surroundings and discovered a beautiful garden with a pool, where we lounged and relaxed after the long drive.

As the sun began to set, we headed to the hotel's restaurant, which served delicious Tuscan cuisine. We indulged in a sumptuous meal accompanied by some of the best wines from the region. The food was so good that we decided to come back for breakfast the next day before we hit the road again.

As we retired to our room for the night, we were already looking forward to what the rest of the trip had in store for us. The adventure had just begun.


I couldn't wait to explore the Tuscan hills, and the next morning we set out early, greeted by a refreshing temperature of 65 degrees. As we made our way through winding roads, I remember turning off onto a smaller road and being met with a breathtaking view of cypress trees and morning fog, bathed in beautiful light. But our excitement was cut short when Gabriel realized he had left his passport at the hotel safe box. After calling the hotel, we learned that the housekeeping had found it. So we turned back, retrieved the passport, and headed to our original destination.

Our first stop in Tuscany was Montefioralle, a charming town located in the heart of the Chianti region. Despite the setback, we were eager to explore and take in the sights and sounds of this picturesque town. We spent some time walking around, capturing photos of the stunning landscape, and soaking up the atmosphere. The beauty of the Tuscan hills was truly captivating, and I knew we were in for an incredible journey ahead.

Greve in Chianti, Panzano & San Gimignano

As we left Montefioralle behind, we continued our journey to the next destination in Tuscany: the town of Greve in Chianti. With rumbling stomachs, we found a cozy restaurant for lunch and indulged in delicious local dishes accompanied by a glass of Chianti wine.

On our way to San Gimignano, we made a spontaneous decision to stop in the small village of Panzano when we saw that they were hosting a wine festival. As wine lovers, we couldn't resist the opportunity to sample the local wines of the region. We parked our car about a mile away and walked uphill to reach the festival. After paying a small fee of 15€ for a wine glass, we spent the afternoon sampling different wines and enjoying the festive atmosphere.

As the sun began to set, we made our way to the medieval hilltop town of San Gimignano, where we had booked our accommodation for the night. Walking through the cobbled streets, we couldn't help but marvel at the impressive towers and historic buildings that surrounded us. It was the perfect ending to a day full of unexpected delights in the heart of Tuscany.

Monteriggioni & Siena

As we drove away from San Gimignano, we couldn't help but admire how stunning the town looked from its surroundings. Our next destination was Siena, but on the way, something else caught my attention. In the distance, I could see a small village perched on top of a mountain with a round fortification. It looked so intriguing that I immediately pulled out my phone to identify it. It turned out to be Monteriggioni, a walled town famous for its medieval fortifications and watchtowers. Without hesitation, we made our way there. As we entered the village, we were greeted by a magnificent fortress wall that surrounded the town. We walked along the walls and enjoyed the breathtaking views of the Chianti region. After exploring the village and enjoying some coffee, we continued our journey to Siena.

As we drove towards Siena, the rain began to pour down. It was late afternoon when we finally reached the city, but we were determined to make the most of our time there. We dropped our bags at the hotel and set out to find a restaurant with some great reviews. Unfortunately, the one we had in mind was closed. So we walked around for a bit and stumbled upon a place called La Taverna di San Giuseppe. The lady at the entrance asked if we had reservations, but we told her that we were just visiting for the night and had been recommended this restaurant by a friend (I always say the same line, I thought to myself). She told us to wait, and said that she might have space for us in about an hour.

We decided to take a walk and explore the city while we waited. The rain had stopped, but the air was still damp and chilly. We took some pictures, marveling at the medieval architecture and the quaint little alleyways. An hour later, we returned to the restaurant and were finally seated. The aroma of delicious food wafted through the air, and we eagerly awaited our meal. And let me tell you, it was worth the wait! This was some of the best food we had tasted in Italy.

The next morning, we woke up to a sunny and breezy day, ready to explore the city. We couldn't wait to see what Siena had in store for us.


As we left Siena and headed towards Montepulciano, we couldn't help but feel a sense of excitement for what awaited us in this medieval hilltop town. As we approached the town, the winding roads led us through vineyards that seemed to go on forever. It was as if we were driving through a painting, with every turn revealing more and more of the beautiful landscape that surrounded us.

As we made our way into town, we were greeted by the charming and quaint streets that Montepulciano is known for. After a few wrong turns and accidentally calling out the owner's name at the wrong property, we finally found our accommodations for the next two nights. The owner was kind enough to welcome us with a bottle of their own vino noble red wine, and we couldn't wait to sample it.

After settling in, we made a quick trip to the supermarket to pick up some groceries. On our way back, we noticed some beautiful stormy clouds forming in the distance. With my camera at the ready, I was able to capture some stunning shots of the sky, adding yet another layer of beauty to this already breathtaking town.

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