Tuscan Cities Mentioned In This Post: 

  • Montepulciano
  • Pienza
  • Siena
tuscany digital nomads

Tuscany, Beautiful Tuscany

Early in the courtship process, there are often many new and unexpected discoveries both sides learn about each other. Some of these enlightenments are minor bumps along the way while others may threaten to end a relationship before it has really begun. Our young love with Tuscany was not unlike most new couples. At first we were captivated by her beautiful rolling hills, majestic landscapes and the fact that this was truly the vision of the dream from many years ago. As we became acclimated to one another, some of Tuscany’s cooler side (quite literally very cold) came out to bite us unexpectedly.

Tuscany is a very high-class type of gal. Everything about her seems to reflect power, confidence, fashion and luxury. That kind of status comes with a price, however, which was much the opposite of our experience in Split. She is very rooted in tradition, which is evident in her well-preserved countryside hilltowns, cobbled streets, extensive landscapes of grass, vegetable crops, trees and water.

As the weeks have rolled by, Tuscany has played with our hearts at all turns. Whether it was the highest highs of amazing trips with new friends, or the lowest lows of isolation from technology, overspending and disoriented wanderings, she has provided us with quite an adventure. The following stories are an account of some of our top cities visited so far. We hope you enjoy!


Montepulciano Digital Nomad

Montepulciano – Piazza Grande

Home! At least for about a month. When we first arrived here we had actually left Rome early due to a more stressful vacation than what we had planned. The pace here and throughout most of Tuscany is quite a bit slower than Rome as well as back in Croatia. Work starts a little later as it is very important to have a nice long coffee and piece of pie to start most days. We also take a longer lunch and enjoy a coffee after lunch. If something doesn’t get done it is not such as big a deal.

The views are breathtaking. I can recall being worried before we arrived that we would miss the view of the water, being so far inland. Luckily looking roughly 25 kilometers east we have a great view of Lago Trasimeno, which is just across the border into Umbria. The prefix “monte” stands for mountain, which is no understatement. With the supermarket and open air market both at the bottom of the city and our place plus the coworking space near the top of the city we manage to get a workout in nearly every day.

There are several large churches in and around town, all of which I believe we’ve visited now. Our favorite is San Biagio, the more iconic domed church featured in most photos of Montepulciano. On our first walk down to the church after our arrival, the bells were ringing and the sun was beaming brightly. We got to experience Easter Sunday mass there, full of parishioners, incense and echoes of a mixed Latin/Italian sermon. Biagio is even further down the valley, which makes for a super easy walk down and a more or less breathless walk back up.

Co-Working here has been wonderful as well. Wisionaria (our coworking space) is located conveniently right in the main square of Piazza Grande. They recently upgraded to fiber internet connection, which the first company in this region to do so. In addition to getting to know people at the space, we’ve become good friends with Max and Simona and gone on several day trips with them around the area!

San Biagio Church

San Biagio Church

The food is of course amazing. The handmade local pici pasta, pecorino cheeses, wild boar, Chianina beef, sauces and other delicacies are always cooked to perfection and topped off with a side of bread. Danielle got the go-ahead from the doctor to start reincorporating certain foods so she’s started to enjoy a glass of wine and perhaps a little pasta here and there as well.

The town itself was very empty our first few weeks, but since Good Friday arrived last week the town has been quite busy! It’s interesting how much we took the offseason for granted. Soon we’ll have to start waiting in lines, making dinner reservations and battling hoards of travelers instead of simply just walking into a half empty space. We’ve also made friends with the local butcher, cheese shop lady and the people at our favorite coffee spot, Caffe Poliziano!

Our only real issue here has been access. There is not much in the way of public transportation outside of a few local bus routes so getting to an appointment or to and from the train station is more costly and time-consuming. Having friends with a car and who like to travel on the weekends has been such a blessing, allowing us to tour many parts of Tuscany with someone who has actually lived there!


pienza digital nomad

Duomo Di Pienza

Our first experience of Pienza was a rather unfortunate occurrence. Read more about that in this how-to guide. However our second go around was with Max and Simona on Good Friday, which was an entirely different adventure. Having already seen the city, walked the shops and meandered around town a few weeks earlier we were very much looking forward to our night out with some locals. Pienza is known for many things including being the home of Pope Pius II several centuries back, some pagan worshipers (magicians) several centuries before the Pope and more recently the home of the best cheese in all of Europe (PECORINO DI PIENZA).

Fun fact from our friend Max, pecorino cheese is not actually original to Tuscany. In fact, it really came from islands like Sardinia and Sicily where sheep more typically graze. Apparently many areas of Tuscany used to look a lot more like forest and brush than the rolling grassy hills we see today. Moving back to Pienza, we’ve heard from multiple sources (most of them biased) that Pienza does produce the best cheese ever and since our arrival have eaten many varieties (Cugusi is the best brand) to support their claim.

Our dinner reservation was at La Bandita Townhouse, one of the really higher end restaurants in town, but a great value for the quality and uniqueness of the food. As we sat, consuming tasty appetizers, pastas and meat, a processional passed through town and down our street. In front, hooded white figures with cloaks (a bit scary at first as they looked just like KKK members) marched on followed by Jesus covered on the cross and a crowd of warmly dressed locals. This processional was a representation of the Passion of the Christ. 

We concluded dinner with delicious white chocolate and coffee gelato, salad (for Dani) as well as some coffee to keep us awake a little while longer. Then we headed out into the street to watch as festivities wrapped up near the main church square. Strolling the streets of any of these Tuscan towns is a delight, but it was great being able to experience it with our new friends.  


sienna digital nomad

Palazzo Pubblico

The city of Sienna didn’t get a fair assessment from us to be honest so I’ll keep this one short and sweet. The day we arrived, was the day we accidentally lost Dani’s phone on the bus, so it was a costly and time-consuming ordeal to get to Sienna as well as to find the phone once we got there. A bit burned out already, we walked the streets up around and down into the main square in search of a nice meal and a bit of down time. Piazza del Campo was beautiful and covered with people out enjoying cool sunny afternoon. 

We searched around for a bit to find a good food spot and settled on a small tucked away restaurant between del Campo and the Duomo. Cold to the bone, our waiter sat us near the door to keep us at a nice chilled temperature. The food was the worst we’d had and cost 50 euros. It also took forever to arrive so our short window of time in the city dwindled quickly. Afterward, we wandered aimlessly trying to find a fun activity and ended up going back and forth a few times before finally settling on the Museum of Santa Maria Della Scala. The inside was poorly lit, disorganized and had no real interpretation, but we did our best to explore most areas. 

The highlight of the trip for me was when we stopped by a fancy looking Gelateria and got one of the best ice creams I’ve ever had in Italy. It was hazelnut and coffee with Aztec chocolate. Then we left! I think eventually we’ll return, perhaps with some friends on a day trip to give it a fair shake. 

P.S. Sorry for this crappy review Alyssa, maybe we can visit again when you come to Europe next year?

That’s all for now folks! Hope you enjoyed possibly our longest post yet!

– R