Although my final destination was Tuscany, I flew to Rome since it was much more affordable than Florence. I decided to make the most of it, and overnight there to get a taste of this historical city. My hotel was basic but it met my minimum requirements — my own private room with a bathroom, and it was within walking distance of all the major sites.

After taking a short train from the airport to the central train station (which is very snazzy and safe by the way), I put my feet up for a bit (I never understood this “putting one’s feet up” until I hit 50) then decided to venture out for dinner. A quick Google search for a pizzeria near the hotel came up with a decent sounding place with good reviews, so off I went.

I found the prices surprisingly affordable for a big city: 8 euros for a vegetarian pizza and 5 euros for half a litre of wine. I thought oh half a bottle of wine, that’s a bit much, but I don’t have to drink it all… then a large glass carafe was put in front of me, and I thought oh shit my math didn’t math very well, did it. I had forgotten a bottle of wine was 750ml, not a full litre. At which point I turned to the Brits sat next to me and said oops I ordered too much wine if you want some. So I then had a nice chat with them over dinner and they told me they did a tonne of research for where to eat, and travelled quite far to get to this particular pizzeria. I felt fortunate that I happened upon it fairly randomly. The Brits and I are now following each other weirdly on Facebook.

The next morning, instead of taking the hop-on-hop-off bus (which I’ve actually never done, but it seems like a good idea) I decided to walk to the coliseum. It was a beautiful day, a mere 32 degrees which was a sight better than the 44 I had just left in Egypt. The walk was very pleasant, and I didn’t have time to actually go inside the coliseum (that will have to wait for another visit) but I walked around and took a few photos. There were a tonne of tourists milling about and of course touts selling everything from artwork to bus tours to trinkets.

Since Instagram travel “influencing” has become all the rage, I am seeing many young women in flowing clothing and big sun hats posing in front of ancient monuments. I am struggling with my feelings about this trend. Why do I find it so annoying? I do stop short of ruining their photos on purpose, but I refuse to change course and don’t care if I get into their shot. I am here to enjoy myself too, dammit. God I’m getting old.

I was at the train station with plenty of time to catch my train to Tuscany, but the platform was not listed until the last minute, then the glass doors to the new (long) platform were closed. I went around to the little doors, scanned my QR code and got in that way. Then I had to navigate around to the long platform, when I saw some people running past me. I realized they were probably headed to my train too, and then I saw a sign saying that it was like a five minute walk to the platform! It was getting tight and so I started running too, looking like a fat camel with my squishy Disney shoes and heavy backpack and front pack too.

I barely made the train along with a few other sprinting tourists. Three minutes later, the train took off and a few people were left behind. I felt sad for them, but also glad it wasn’t me.

I had more train drama at this remote stop, when everyone got off. The train turned off its engines and the train officer looked at my ticket and told me to get off the train to transfer. He spoke no English, and I spoke no Italian. My train said “direct” … I wasn’t meant to get off. But he told me to get off, so I did. I checked the signage, and it was displaying the train I was supposed to be on. And it was leaving in five minutes. I saw the conductor again, and said “I don’t know what to do”, then he pointed at the train and told meet get on. WTF, dude. So I got back on, and I made it to my destination. That guy was on crack.

I was picked up at the tiny Valiano train station by my host Lucia. She was very chatty and was telling me all about her work drama (she is a school teacher — more on that later) and drama around the water situation at the agritourismo (more about that later also.)

The place was really beautiful, with a pool, nice view and we had a whole two bedroom stone cottage to ourselves.

My sister Emma and her hubby Hans were schedule to arrive later than evening as they were renting a car in Florence and driving. I hadn’t brought much food with me as all the food at the train station was greasy cheese pizza etc. I’m not very good at planning sometimes.

So it turns out Emma’s and Hans’s plane was very delayed and they didn’t arrive until quite late. They managed to text me and I begged them for some food as I was about to gnaw my fingers off. They kindly brought me a slice of potato pizza.

The next day, we visited hilltop village Montepulciano. It was interesting to see the contrast between the tourist demographic there. I noticed many more Italian tourists there vs. Americans and Brit’s in Rome. We had a couple wine tastings, a yummy homemade vegan dinner and dip in the pool.

We then visited Pienza and Torrita Di Siena. We found some pizza and decent house wine in a nice restaurant. A cook came out and clutched his head at a poor foreign guest, then he pulled up a chair. While waving his hands around and laughing he explained that no he cannot put ketchup on the pizza, otherwise saint Peter would meet him at the pearly gates and not let him in. He was just trying to save his soul. We were laughing hysterically but I think the guest was really embarrassed and didn’t say a word.

Then we found a genuine Donatello sculpture in a small empty church in a very quiet town. There we were also escorted by a man who had something to do with the local counsel. He showed us the council room with a fresco on the ceiling and the flags used for the annual donkey race. Similar to Siena but with donkeys 🤣. Then after dinner we went for a sunset walk in the vineyards and took some fun photos.

On another day we drove to Cortona, home of St. Francis of Assisi’s first church. It was very peaceful there. Then we had the most incredible lunch at Osteria de Theatro. You know when you have those food experiences that stick in your memory? I tried the goat cheese, pear and walnut fagioli. Hans’ gnocchi was delicious too. Emma had the spinach and truffle ravioli. We visited a couple churches and stumbled upon a gallery selling limited edition Picasso and Dali prints. Should I move here?

In the four days we were there, we lost wifi for half a day, the water in the shower didn’t drain, we had ants and gnats, and for 24 hours there was no water. I let Emma deal with it. 🙈🙈🙈. We asked for a discount and Lucia just shrugged in that classic Italian way and said “I’m just a teacher.”

Regardless, we had another awesome day in Montepulciano. We toured De’Ricci winery in a cave and had a tasting. The winery has a really interesting history. The mascot for the winery is a hedgehog because back in the 12th century, there was a poor boy who could predict weather with such accuracy that he was charged with sorcery! To save his life he had to tell the tribunal his secret — that he watched hedgehogs interact with the sun’s patterns. He was then appointed to the court, became wealthy and used his riches to help the town’s impoverished. To learn what happens next, go and take the tour! You won’t be disappointed.

We then had a capuccino and tiramisu in a gorgeous cafe from art nouveau days. We sat near the balcony and had random people off the street standing next to us taking photos out the window.

We moved accommodation to a hill town called Volterra for a couple nights. Not a lot of tourists there, which allows for a more authentic Italian experience. On the way, we stopped to see the Siena town square including the gorgeous duomo and the site of the annual horse race. 🏇 For dinner I had delicious fresh pasta called spaghetto…which I initially thought was fat spaghetti, but it’s just the singular form for the word spaghetti.

We then visited the beautiful yet touristy hill town San Giminiano. I ate a fabulous gelato, saw some Lego art, watched an Irish opera singer practicing for a wedding later in the day and drank a gin and tonic with the best view everrrr.

Rome hotel

Hotel Meridiana

De’Ricci winery

Recommend the tour & tasting.