Arezzo: 2 Days

May 07, 2026

Arezzo: 2 Days

I spent two nights in Arezzo, which is surprisingly a great town to stay and relax. I stayed at The Homestay, which was a nice place to rest and not too far from the attractions, plus it’s next to a supermarket.

You can explore the major sites in Arezzo in half a day or less. These sites include the Arezzo Cathedral, Medici Fortress, Piazza Grande, and a Roman Amphitheatre.

Anne, whom I had met in Florence two days before, took the train to Arezzo. I ended up being her tour guide since I had just visited the above mentioned places in the morning.

One of the cool things about how Anne travels is that she likes to go into interesting stores, such as a cobbler’s workshop and book stores. I rarely pay attention to these things since I don’t buy anything when I travel. So it was nice to see a local cobbler taking a client’s order in a shop full of Italian leather shoes, which is something I definitely rarely see in the States.

I had a great time chilling with Anne by the park outside the Arezzo Cathedral. It had a great view of the mountains in the back and Tuscany houses in the foreground. I felt like I was watching a painting. We also had an early dinner at Borgo S. Piero, a small restaurant that’s run by an old grandmother.

Anne told me the days she spent with me were the best days of her travel in Italy and that she had done Italy wrong all this time since she was staying in major cities. I have to thank my friend Dineke for telling me to check out some of the small Italian towns in addition to the major cities. I also want to thank my friend Omar for connecting me with Anne. It’s always nice to travel with someone.

However, after I dropped off Anne at the train station so she could go back to Florence, she told me she was fined €70 for not having her train ticket validated even though she had bought the ticket from the ticket machine in the Arezzo train station. I was surprised because I had always bought tickets from the machines and no one ever checked my tickets. I didn’t even know how to validate my ticket. Italy surly didn’t treat Anne well.

To be sure that I won’t get fined by not validating my ticket, I bought my train ticket to Rome from the Trenitalia app on my phone so there’s a QR code in case the train conductor checks. And sure enough, on the train a conductor did check my ticket and scanned the QR code. If it wasn’t for the unfortunate event that happened to Anne, I would have been fined for buying a ticket from the machine and not having it validated. I still find it weird that a train ticket has to be validated even though it’s already paid.

Anyway, after about a three hour train ride from Arezzo I arrived at the YellowSquare Rome hostel. I will stay in Rome for six days since there are a lot to do here, judging from the information from other travelers and from my own research.