Toscana for Twenty Sunrises

Taking in the beauty, history, and gelato

(This article was cowritten, so paragraphs beginning with “M” were written by Mollie and ones beginning with “R” were written by Ryan)

M - After our sprint through Scotland, France, and Switzerland, we knew we needed to land somewhere for a good long while. This fit into our plan of setting up a home base in Tuscany, as we had fallen in love with Italy when we visited two years prior.


**M** - We chose Arezzo for this very purpose. Arezzo is a smaller city, somewhat off the beaten trail, but it sits along the high speed train routes- about an hour south of Florence and one and a half hours north of Rome. Having easy access to the trains was important to us because we have Eurail Global passes and Arezzo's central location made it easy to take day trips to other parts of Italy.

M - Unsurprisingly, after our sprints through the UK, Paris, and Switzerland, we didn’t take full advantage of being able to explore by rail. We ended up taking fewer than five day trips. Honestly, we were super happy to put up our feet and enjoy Arezzo! It’s a laid back place, populated by friendly locals. It has a farmers’ market (open six days per week) to enjoy, beautiful vistas, and usually we were usually the only tourists around. It was a stark contrast from Florence where it feels as though English is more widely spoken than Italian. Don’t get me wrong, we loved Florence when we visited two years ago and highly recommend it to anyone who hasn’t been before. However, considering we’d explored Florence at length before, we didn’t feel the need to spend great lengths of time there on this trip.

M - We found a great Airbnb up the hill, within the historic part of the city, complete with the typical Italian shutters and lack of window screens. The first few nights Ryan was getting COVERED in mosquito bites. Apparently he’s tastier than me, as I pretty much came away unscathed. By day four, we opted to build our own window screen for the living room so that we could air out the apartment. This meant going to a mom and pop hardware store and explaining (in Italian) that we needed a large roll of screen netting and some thumb tacks. Did I mention that the ceilings, walls, and floors were all concrete? This meant we had a perpetually damp-feeling ground floor that desperately required open windows during the day. I know I’m not painting our experience here as particularly nice, but I once we had built ourselves a screen it all worked out beautifully.

M - The roads outside were narrow and made up of giant paving stones. However, this didn’t stop cars from driving down our street at terrifying speeds, but this seemed to be typical for Italian drivers. A highlight of Arezzo was the Mercato Logge del Grano- an indoor farmers’ market with local produce, olive oils, wines, pastas, beer, etc. On days we didn’t feel like cooking, we would go to the market’s upstairs bistro for lunch. For 12 euro per person we could get a full meal that was created and inspired by the very produce being sold at the market. The meals were simple but so, so delicious. Also, the staff were all fantastic and very friendly- even with a language barrier.

M - Another highlight was our favorite gelato place- Gelateria Artigianale Sette Voglie. It had the best hazelnut and pistachio gelato we’ve ever had, seriously. Here we also ran into a language barrier, but that disappeared after the fourth visit when the shopkeeper realized Ryan spoke Spanish. As it turns out, she was from the Dominican Republic. It’s amazing at how language can either bridge or separate you. Mirabelle, the shopkeeper, recognized us as American tourists who love gelato and was always nice to us, but our conversations were extremely limited. Once we realized each party spoke Spanish, we began to exchange names and stories, and Mirabelle was able to give us some local tips. It was really nice to connect with someone like this, especially on a trip like ours that frequently leaves us somewhat isolated.

M - If we weren’t at the market or eating gelato, we would wander the crooked streets of Arezzo, getting lost in the old city only to turn a corner and discover we’re just a block away from home. We enjoyed sitting in the park at the top of the hill, watching the clouds form and disperse over the verdant olive groves and terracotta red rooves 1. We got into our yoga routine again, after a long break from Argentina. We finally caught up on our blog posts, which unfortunately did not last long 😋 To put it simply- we lived La Dolce Vita!

R - Our time in Arezzo was fantastic, and a much needed respite after our quick dash through the UK, France, and Switzerland. I won’t reiterate what Mollie already said, but I’ll mention a particular experience she didn’t cover above- our visit to Caffe River. I have a blurb written about them in our Coffee section.

R - I wanted to see if there was any specialty coffee available in the Arezzo area, though I was keeping my hopes low. The only result on Google was Caffe River. I reached out to them asking if their location was a cafe or simply an office, and also to ask if they had any recommendations for coffee in the area. Marco responded to my email to explain what I had already suspected- Italians for the most part have no interest in third wave coffee, to say nothing of pour over. They’re also very price sensitive with regards to coffee which makes it hard to offer specialty coffee with a corresponding higher price, as no one would buy it.

R - However, Marco also invited us to go visit their headquarters to get a tour of the facility, and to roast some coffee with them. I’ve never gotten a tour of a roastery before, so of course I jumped at the chance.

R - The facility was impressive, and getting to see the sorting, roasting, and packaging processes were a great experience- very interesting to a coffee enthusiast. We also headed to their lab where we were given the opportunity to check out samples they’d been sent from their coffee farm partner. This included seeing coffee cherries and beans in various states I hadn’t seen before. Daniele (the head roaster) then pulled out their Ikawa Roaster and asked us what type of roast we’d like for our coffee. You can see the video of the roasting here.

R - We spent all afternoon at Caffe River’s HQ, and it was a fantastic and unique experience. We very much enjoyed talking coffee with Marco, Elisabetta, and Daniele. Caffe River sent us home with three different coffee samples that they’d roasted for us on the spot- a Costa Rican, a Brazilian, and a Ugandan. The visit was easily one of the highlights of our time in Arezzo.

R - Aside from that, as Mollie said, we spent a lot of time just hanging out and living normal lives in Arezzo- exploring the town, cooking, and eating out. It made for a fantastic refuge, and provided us with an authentic Italian experience in a place that feels very local and non-touristy. However, one thing I don’t miss about it is the bread… Tuscan bread is the WORST. For an area with otherwise excellent food, it’s a weird blind spot. There’s some debate about why Tuscan bread has been made without salt for centuries. Regardless, in my opinion, it’s a tradition that should be corrected- it’s truly terrible, but I guess it’s good if you’re trying to cut carbs since it won’t tempt you at all.

R - An additional anecdote I almost forgot to include: We had a very Seinfeld-ian experience while in Arezzo. One day we went out to eat at a restaurant, and I discovered the owner had lived in Chile for a year, so we chatted a bit in Spanish.

R - As we sat down at one of the restaurant’s outdoor tables to enjoy our meal, a hawker/beggar came over to the tables to ask for money (or sell something, I wasn’t quite clear on that). As other tables declined, he arrived at our table and asked in Italian. I responded “no Italiano”. He then broke into perfect English and repeated his request. I figured the easiest course of action to be left alone was to pretend I didn’t speak any English, so I responded “perdon, no hablo Ingles o Italiano, solo Espanol”. He gave us an exasperated look, and sat down at the empty table a few feet away from us. Apparently restaurant owners give beggars free food in Arezzo, because soon the owner came out to give him some food. This was incredibly awkward, because it meant that Mollie and I now had to continue our lunch conversation exclusively in Spanish in order to maintain the pretense that we didn’t speak English. Thankfully as I’d already been speaking in Spanish to the owner, when we went to pay I continued to speak exclusively in Spanish. The whole situation felt like something George Costanza would find himself in.

R - A few days later, we were at a sandwich shop paying for our order. The woman working the counter knew English and we were interacting in English. We heard the bell ring as someone walked into the shop, and someone got in line right behind us. Of course, it’s the same beggar, coming in to get free food from the sandwich shop. Cue music. I was stuck continuing my interaction with the cashier in English, and I just hope he didn’t recognize us 😂.



**M** - We could not come to Tuscany without a stop in Florence, no matter how many Americans are there! We spent two years wishing to relive our last trip to this city, so that's exactly what we did. We went back to our favorite mozzarella bar - Obica, our favorite gelateria - DONDURMACI Gelateria Della Passera, and walked back around to see the Duomo and Ponte Vecchio. Obica was slightly disappointing and we were sad to find that "our" hidden little gem gelato spot had a line out the door of English speakers 😭😭

R - There was a lot of nostalgia to be had in Florence. We were able to navigate it surprisingly well from memory, as we were walking through streets we’d learned pretty well on our previous visit there. It was disappointing to find that it somehow felt even more touristy than it was two years ago. As such, we didn’t spend too much time revisiting it. That being said, if you haven’t been before, Florence is a must- the architecture, the Accademia Gallery, and the Uffizi Gallery are not to be missed.


M - Oriveto is a small, typical Tuscan hilltop village that Rick Steves “discovered”. This was a quick trip from Arezzo, free with our Eurail passes. Unfortunately, all the good food options we had scoped out beforehand were closed (seriously though, what restaurant is closed on a Thursday?!) so we ate mediocrely. We still enjoyed finding a quiet bench that overlooked the hillsides nearby, near a church built in 1300CE.

R - Orvieto is charming, but I found it to be surprisingly touristy. However, it was a nice change of pace from Arezzo. Arezzo very much feels like a “real” city, meaning that in addition to the historical center, it also has less charming blocky modern buildings, normal traffic, etc. Orvieto feels more like a preserved historical town, making it seem far more like an Italian fairytale. This of course makes it far more attractive to tourists, so you end up finding a lot of overpriced food and kitsch- a definite trade off.

R - We were glad to have visited Orvieto as it was a nice change of pace, with beautiful architecture, picturesque narrow roads and paths, and beautiful hilltop views. We were also glad to be heading back to sleep in Arezzo where we felt much more at home and less like we were in a tourist trap.


**M** - Famously known for Saint Francis of Assisi, this town far exceeded our expectations. It was exceptionally clean and had the old city Jerusalem stone feel- the same white rocks as paving and building stones. We listed to a Rick Steves tour here that brought us from a Roman amphitheater to the monastery. It seemed like every windowsill had beautiful flowerboxes- apparently there is a competition each year in June for the best flowerboxes.

R - Assisi is beautiful. Like Orvieto, it’s a historic hilltop town, but even more impressive to look at and walk through in my opinion. The city is incredibly well-kept, and despite having tourists, it didn’t feel as touristy as Orvieto did- possibly because most of the tourists here are actually pilgrims. Part of the reason the town is in such excellent historical condition is actually due to the Black Plague, which sent the city spiralling into deep decline. This meant that while other nearby towns continued to thrive and modernize with the times, Assisi basically stayed the same as it was. The pink stones used throughout the city come from Mount Subasio, and give the town a very distinct look- as Mollie mentioned, a similar feel to Jerusalem Stone. Even if you’re not particularly interested in the religious component of the city (like me), it’s definitely worth a visit.


**M** - The Eternal City. Like Assisi, we also were blown away with Rome. It was incredible to be walking along the street to suddenly stumble upon ancient ruins! We toured the Colosseum, the Forum, and the Pantheon (thank you Rick Steves audio tours!). We took a Rick Steves audio tour of the Jewish ghetto, the residential neighborhood across the Tiber River called Trastevere, and his Rome city walk tour. We walked over 34 miles during our two days in this city! Our legs felt like jelly the following days!

R - We went to Rome twice in the same week- it was our last week in Arezzo, so we took a day trip on Monday to Rome, and we also went to Rome on Thursday. Thursday morning we checked out of our Arezzo Airbnb, took the train to Rome, spent the entire day there, and then took the overnight train to Syracuse (a miserable experience I don’t recommend). As Mollie stated, we walked over 34 miles in Rome- over 15.5 miles on Monday, and over 18.5 miles on Thursday, so we covered a LOT in the two days there.

R - Rome is an odd place. It’s an ancient city that has been thrust into the modern age as one of the major cities in Italy. Everywhere you look there are historical sites randomly strewn about the city, both minor and major in significance. We did a ton of Rick Steves audio tours as Mollie mentioned, all of which were great. We found some decent food, but unfortunately, much like Florence, Rome has become VERY touristy, and as a result the food tends to be overpriced. You can find great food for reasonable prices, but not in the parts of town that house the majority of the tourist attractions. 34 miles of walking over a two day period is way too much, we ended both days absolutely exhausted. I’d recommend either spacing out Rome for longer (maybe four days rather than two), and also suggest getting around using transportation other than your own two feet. That being said, getting to see the Colosseum, the Forum, the Pantheon, Palatine Hill, the Trevi Fountain, the Jewish ghetto, Trastevere, etc was fantastic. We also took the opportunity to go see the Vatican.

Vatican City

R - I wasn’t sure how I’d feel about the Vatican before going there. However, our introduction to the place was quite negative. We arrived at 3:00 PM, knowing that ticket sales to the Vatican museum stopped at 4:00 PM. Immediately we were approached on the street by a guy trying to sell us “Skip The Line” tour, telling us that the hour to buy tickets was over two hours long and we wouldn’t make it in unless we took one of their tours. We politely declined, despite his protestations.

R - As it turned out, we had approached the Vatican from the southeast (St. Peter’s Square), but according to Google Maps, the ticket sale booth was on the north side of the Vatican. We began walking around the Vatican to get to the booth, and we were absolutely mobbed by these guys trying to sell “Skip The Line” tours. We saw them aggressively trying to sell to other people as we walked by as well. We finally made it to the area where the entrance to the ticket area was, but as we didn’t see ANYONE waiting to get in, we were unsure if we were in the right place. We stopped nearby a moment to check our phones, at which point no less than six people came over to us individually to try and sell their tours. At this point I reverted to my default which was to pretend I spoke no English or Italian, only Spanish. I could see them visibly upset that I was claiming I didn’t understand what they were saying, and they would throw up their hands in exasperation and walk away. Eventually we confirmed we were in the right place, and walked in. Shocker- there was one person in line in front of us, and we were inside within two minutes. It wasn’t exactly the “over two hour wait” those annoying tour hawkers were trying to convince us existed.

R - Worse yet, we discovered reading online that the “Skip The Line” tours were even more of a scam than we had thought. Entry to the Vatican is 17 euro when purchased at the box office, and the “Skip The Line” tours were advertised as somewhere between 23-27 euro- a slightly higher price. While they’re not lying about “skipping the line” (assuming there is one), what that really means is that you go through the entrance for tour groups rather than individuals, at which point YOU STILL HAVE TO BUY A TICKET. Most people badgered into buying these tours are doing so with the belief that they’re paying slightly more for a tour which includes price of admission, when in reality it most certainly does not. This made me extra glad I ignored those guys, who I wouldn’t have bought anything from on principle by virtue of the fact they were UNBELIEVABLY annoying. The Vatican would really benefit from clearing those guys out of there, as they really sour the experience for anyone even trying to walk to the entrance of the Vatican- there’s no way to avoid getting mobbed by these assholes.

R - Finally we made it inside, albeit with me in quite a bad mood. We decided to hightail it to the Sistine Chapel since that was our primary point of interest. For some reason the Vatican had the “short path” closed off, which meant we had to go around and through various other exhibits in order to eventually reach the Sistine Chapel. The sheer opulence and breadth of the collection was astounding, and to be honest, disgustingly avaricious. Displays of wealth rarely give me such feelings of negativity, but it felt like the Vatican was just HOARDING precious artifacts, art, and wealth. Especially given the brutal and bloody history of the church, it felt simply wrong that I was being charged 17 euro to go in and see all this that had been taken from society and amassed over centuries.

R - Eventually we made it to the Sistine Chapel, and listened to the Rick Steves audio tour for it. The Sistine Chapel ceiling is a wonder, absolutely worth seeing, and likely the greatest painting ever produced in the history of humanity. At one point however, our audio tour was interrupted by a priest who called out over the microphone to lead people in prayer. Despite the annoyance, it was hard to feel too upset given that we were in a chapel after all. However, it was a reminder of what I mentioned above- the greatest painting in the history of humanity wasn’t located in a museum, it was tucked away in the beating heart of the Catholic Church, in a chapel. The work of art wasn’t necessarily what Michelangelo would have wanted to paint, it was a religious work commissioned by the Church. Despite the impressive beauty and size of the work of art, it was a stark reminder of the power and influence the Catholic Church wielded over Europe and the world for such a long and dark period of time.

R - After checking out the Sistine Chapel, I felt like I’d had my fill of Catholicism for the day. So rather than see St. Peter’s Basilica, we opted to head back out into the city of Rome. I don’t think I ever need to go back to the Vatican, but seeing Michelangelo’s Sistine Chapel ceiling is a must for anyone who finds themselves in Rome at some point in their lives.

1 - For those curious: Rooves is not incorrect but is a dated plural of roof, used in the UK and New England. Ryan thought I was making it up

DWNTGB (Do We Need To Go Back) Rating

Ryan -

Since we’re not doing DWNTGB ratings for each individual place on this list- rather just doing it for Tuscany as a region, my answer is a resounding yes. There’s a lot more to be explored in Tuscany, and even if I’m not there for exploration, it’s a fantastic place to set yourself down to relax and enjoy life.

Mollie -

Yes, there’s more to Rome that I would like to see, plus I would love to tour the Duomo in Florence, and explore Cortona as was recommended by Mirabelle. And there’s always more gelato to eat…

Conclusion: Take Us Back

See also