• Gary Rosado

Italian Road-trip

Updated: Feb 10, 2021

For those who know me, you all know I love to travel and usually I take the month of September off to go somewhere to relax, recharge, and get inspired. This time it was Italy's turn, a country that I've visited many times but this one I wanted to repeat some cities and discover other ones for the next 21 days stay. We arrived in Venice, rented a red Fiat 500 (you can't get more Italian than this) and drove to the outskirts of Florence where we spent the night at this beautiful hotel called Hotel 500 Firenze


Next morning very early with a pleasant temperature of around 65 degrees we continued our journey to the Tuscan hills. I remember how excited I was when I made a left turn off the main road and after some minutes the road opened up to a great view, the one I had in mind after looking at some many pictures. Lots of cypress trees, a bit of morning fog with beautiful light. All this excitement didn't last that long after realizing that Gabriel left his passport at the hotel safe box! We called the hotel to verify and the housekeeping found it, we turned back, got the passport, and returned to where we were. The first area of Tuscany that we explored was Montefioralle, a small town in the Chianti region. It was a quick stop to walk around and take photos like the ones seen below.

Greve in Chianti, Panzano & San Gimignano

After a quick stop in Montefioralle, we continued to the town of Greve in Chianti where we had lunch. Passing through Panzano, we noticed they had a wine festival, and since we are wine lovers we found a parking spot about a mile away and walked uphill to participate. This wine festival is held in the 3rd week of September and we were lucky to be here at this time with no planning. We paid around 15€ for our wine glass and we sampled all the wines from the region, this was a pleasant surprise. By this time it was around 4 pm so we continued to San Gimignano where we spent the night.

Monteriggioni & Siena

The following day, we walked around San Gimignano and visited a medieval water cistern. While driving away, we could appreciate how beautiful this town looks from its surroundings while we continued our journey to Siena. On the way to Siena, we saw at a distance a nice round fortification village on top of a mountain that caught my attention. I pulled out my phone, and found out that it was Monteriggioni, immediately found the way to get there. Monteriggioni is a walled town known for its medieval fortifications and watchtowers. The castle walls offer views of the surrounding Chianti region. After some coffee, we continued our way to Siena.

We made it to Siena by late afternoon under some rain, dropped our bags at the hotel, and drove to the city looking for a restaurant with some great reviews. To our surprise, it was closed but we walked for a bit and found a place called La Taverna di San Giuseppe who looked promising. We walked in and a lady asked if we had reservations, we told her that we were visiting for the night and that a friend told us about this great restaurant (I always say the same line LOL) she told us to wait and told us that she might have space but in around an hour. We went for a walk to take some pictures and came back, waited some 30 minutes and we got seated. This was one of the best foods I've had in Italy, the wait was worth it. The next day it was very sunny and breezy we got up early to explore the city. 


After exploring the city of Siena, we continued our journey to Montepulciano which is a medieval hilltop town. Surrounded by vineyards, it’s known for its vino noble red wine. We found our accommodations for the 2 nights we were staying here after entering with our rental car to private property, thinking it was the one and calling out loud the owner's name! LOL. Thankfully no one came out and I noticed we were at the wrong place. A few steps down the road, we found our place and the owner received us with a bottle of wine from their vineyards which was greatly appreciated. After settling down, we headed to the supermarket to buy some groceries, and on the way back we noticed some beautiful stormy clouds in the area just in time, and with a camera on hand like always I was able to get some beautiful skies in the area.

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