Italy, Part 2: Tuscany & back to Rome

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Oct 26-30, 2021

Family Fun


Ahhh this will forever be a day of Hays family travel folklore. The morning started well, quick breakfast and packing up to check out with our Airbnb host. Our plan was to pick up our rental car and drive to Tuscany (wine country) a few hours north. Our goal was to drive to Orvieto for lunch, then check in to our Airbnb in Castellina in Chianti. Josh and I did this trek 12 years ago and we felt it was a proper component for Matt & Tomi’s first visit to Italy. 

To help reduce the abysmal traffic congestion, Rome recently began limiting who was allowed to drive in the city – giving permission only to bus drivers, taxi drivers, and those with special permits. Because of this, we all had to take a taxi to the rental car pickup spot instead of just Josh going and coming back to pick us up. 

We were six people, with luggage, so our only rental option was a large van with manual transmission. Y’all these rental cars were packed in so tightly on the street, that we had to ask the guy who rented to us to get it out of its parking spot. We piled in, ready to start our drive. Josh immediately noticed the gear shifting was a little funny but it seemed workable, and the mind blowing traffic was so much more stressful at that point. Italians make 5 lanes out of 3. In many places there are not even lane lines. Mopeds whip in and out of lanes, and everyone is slamming on breaks every 5 seconds. 

About 45 minutes later we found ourselves on the highway, about halfway to Orvieto. The car was not improving. It wouldn’t shift properly, didn’t seem to recognize the gear and you could hear the engine revving in a not good way. I pressured Josh to pull over to restart the car and see if that helped. Against his better judgement of waiting for an exit, he pulled over. From there, what was a frustrating situation became even worse. The car would not shift into 1st gear. And then not start at all. For the first time ever, Josh purchased the roadside assistance (thank goodness), so we called that number. It is a bit of a blur from there. We had to wait for a phone call to confirm a tow truck, and simultaneously I started calling the rental company to ask them to bring us another car as we were on the side of a highway with trucks blowing past us and shaking the car. The rental car company refused, saying we had to make our way back somehow after the car was towed. And then they would give us a different car. Honestly, if it had been just me and Josh, we probably would’ve just done that. But we had the whole family and all our crap. And I was so angry that this company had such a poorly performing car in its fleet that I (with Tomi’s encouragement) used some pretty strong words to let them know it was unacceptable to leave a family with young children stranded on a highway in a crap car that they provided and they needed to remedy it. NOW. 

Meanwhile our tow truck showed up. The driver was the kindest Italian granddad and when he saw our boys’ faces in the back (who were in tears at this point thinking we would never leave that highway), he explained to us he legally could not take the car and leave us and even though he wasn’t supposed to, he would tow us WITH us still in the car to the nearest gas station. When we got there he also talked to the rental company and gave them his thoughts on leaving us stranded. They still wouldn’t budge. He couldn’t stay any longer with us, but gave us a taxi contact who could fit us to take us to some other destination and wished us luck.  We were in a conundrum. We needed to be at the Airbnb before dinner time as a chef was arriving there to make the dinner. If we returned to Rome, we would end up back tracking and costing ourselves extra hours.  We considered taxiing to a closer town and trying our luck with a rental there, but those cities are smaller, had shut down for the early afternoon, and a car big enough for us was unlikely to be available on such short notice. 

It was time for the big guns and Tomi put her powers to use. I was also on the phone with AmEx (whose site we’d used to book the car), who also called the rental company and tried searching for other rental options (none showed available). Long story short-ish, by the time Tomi, AmEx, and I were done with them, they’d been hit from all angles and reluctantly agreed to bring us a car. 

All told we spent about 3 hours in this limbo world, at a covered picnic area adjacent to a gas station. We at least had access to food, water, and toilets and were no longer on the side of the road. As Caleb said, it was #notideal, but can you really road trip in another country without some sort of crazy story that includes an Italian grandpa who tries to save you and an evil car rental company that leaves you stranded at a gas station? In the rain?

Finally, our car arrived and without much fanfare we returned to the highway. Because we’d lost so much time we had to skip Orvieto, eating lunch instead at the gas station, and make our way as quickly as possible to Castellina in Chianti. We had to make a quick grocery stop to pick up necessities for the house and made it in time to greet the chef who was already cooking. 

Chef Francesco who cooked a wonderful, very welcome Italian meal.

The property of this place was stunning. It had been around for a couple of hundred years and was used during WWII as a lookout point. The property was owned by a family that still operated the small vineyard, producing their own wine (but not selling it).  We arrived at sunset, unpacked our things, and finally took a breath to unwind while our Italian chef, Francesco,  made dinner. We had a sausage bruschetta, a venison meat pasta, a chicken/beans/potatoes soup of sorts (my fav of the whole meal), and oh my goodness the best Tiramisu I’ve ever tried.  It was a great ending to a frustrating day. I was proud of us for the teamwork to get there, glad the boys saw that things don’t always go as planned and you have to sometimes problem solve on the spot. Let’s just hope those times are few and far between!

The Il Villino Farmhouse


Our morning started with a quick breakfast in the villa, then greeting our driver for the day, Alessandro. We had booked a half day wine tour via our host so we were not entirely sure what the day would hold except they promised 2 vineyards/wineries and that it was completely ok for the kids to be there. You might be thinking, “what sort of parents take their kids on a wine tour?” Well, it may not have been ideal, but #protip, if you’re going to do it, do it in Tuscany on a private wine tour. The places we went were so welcoming to us and the kids, and they weren’t even the only kids we saw. 

Our first stop was Poggio Amarelli. We were there early, workers were still showing up, and were greeted by the wine maker, Alessandro, who works with the Mazzarrini family to create some amazing wines. He is newer to the company, which is run by Marco and Adriana Mazzarrini. Alessandro toured us around their facility and introduced us to the family cat, Truffle, with whom the boys immediately fell in love. After checking out where the wine is made and a little of the history, we were taken upstairs to the tasting room, which we had all to ourselves and given a private tasting with Lorenzo, who we all decided needs to be our best friend. We learned about the different distinctions of Italian wines by their own system (DOC, DOCG) and as well as the European Union system (IGT). We talked about how wines have to been tasted and accepted as Chianti Classico  every year or they can not be sold under that name. We tasted 6 wines and were even treated to a 2010 Chianti Classico Reserva that had been opened days prior, is not usually on the tasting menu, but was still good that day for us to try. The presentation, the accompanying snacks (probably the best assortment of snacks I’d had ever at a wine tasting), the personality of the owners + Lorenzo, and the beautiful site, made us all fall in love with the place. It is where we bought the most wine of our trip in Tuscany. 

As we left the place was filling up with bigger groups of visitors to try the wines/eat a bite. I felt lucky that we’d gotten to be there when everything was still quiet. 

When Alessandro  picked us up that morning he’d offered us either 4 hours/2 wineries or 6 hours/2 wineries + lunch. We decided lunch would be a good idea to keep the boys happy so the second place we visited, Tenuta Torciano, not only offered a tour/tasting, but also an incredible 3 course lunch with an 8 wine tasting. Y’all the food was so good, but SO filling. I could barely move.

One surprise from the tasting was finding a white, Vernaccia Di San Gimignano,  I enjoyed from a region I mostly associate with red wines.  This tour was more about the beautiful property/vineyards. We didn’t go in and see any of the facility but mostly learned about the family who still owns/runs the vineyard. The great great grandfather had 18 children, which allowed for so many family members to still remain part of this business. It was a larger feel than our first stop, and I think our taste buds were still biased towards the prior tasting, but we very much enjoyed the vibe, experience, the FOOD, and talking with Leticia, our guide/sommelier, whose grandmother’s lasagna was served to us. It was easily the best I’ve ever had. We purchased more bottles and then had Alessandro drive us back home for an Italian cooking class we’d scheduled via our Airbnb. 

Here’s another blip in perfectly made plans. For one, we were told the chef would arrive at 5:45, but instead she came at 4:45, literally minutes after we’d returned from our wine tours. We’d also booked a 3 course Italian style meal that was to include once course of pasta, one chicken based course, and a dessert. However, there was a big communication error between our host, her husband, and the chef, and Paula (the chef), arrived with materials for making 3 pasta dishes. By this point we’d been in Italy 5 days, had eaten SO MUCH pasta and pizza, that we were looking forward to something more rounded in cuisine and less focused on pasta. That being said, what can you do? So we asked Paula to stay, teach us her magic in pasta making, which we’d never done before, and make three dishes: a spinach/ricotta gnocchi, tagliatelle with tomato sauce, and gnocchi with sage butter sauce. Probably one of the nicest parts of this experience was seeing Josh, Matt, and even Caleb, put themselves to work to make our pastas. They were pretty gung-ho! 


Thursday morning started with an earlier alarm. Matt and Tomi were interested in another wine tour, and I knew the boys needed something different to see/do, so we’d planned to drive to Florence where one group would go on a wine tasting tour we booked on (via TripAdvisor) and the other would do a bike tour around Florence booked through the same site. We left the house by 7:15am to get to town in time. Florence traffic is nearly as stressful as Rome’s for the uninitiated. On top of that, Google maps wasn’t updated on some changes of certain roads to one way only. We were in a large van so also parking became an issue. We dropped off Matt and Tomi for their tour (Josh decided last minute to join the bike tour with the boys and me). The meetup times were about an hour apart so we had some time to deal with traffic and parking, trying to use google to steer us in the right direction. The place we found was on a super narrow street with some sketchy looking guys giving us the “daily rate” that they seemed to just pull out of their butts, but Josh was so happy to not be driving and get out of the car. We agreed and they took the keys from us to park the car. We both crossed our fingers the car would still be there when we returned. 

We grabbed a quick “second breakfast,” as the boys call it, at a nearby cafe, and found our tour guide. We were joined by a Dutch tourist as well and the 6 of us set off on our bike tour, with an earpiece in to hear our guide talk as we rode. Our guide was a native Florentine with an expertise in art history. You could tell she loved her city and encouraged us to go beyond the tour later and see more sites (which we didn’t really have time to do). We learned about the Medicis who had ruled the area off and on for about 300 years. I’m no historian but they were a bit of a mess. They ruled, they got kicked out, they came back. They commissioned art and renovations of churches only to also run out of money. They did, however, influence banking, art, and architecture. And if you think I’m over generalizing here, I am. I leave the true art history explaining to my SIL 😉 And wikipedia if you aren’t lucky enough to know her. 

One of the things that stuck out to me was a particular square – Pizza della Repubblica. Originally this was the site of what would have looked like the roman forum, with temples, a market place, and other very very old structures. In the 19th century, Florence became capital of Italy, which lasted only about 5 years. Around this time, it was decided that Florence needed a more modern look so they actually destroyed all of the older forum buildings around this square, and many medieval buildings throughout the city. They wanted a “modern” palatial look in that area and while it is pretty and still “old” by typical American standards, it is crazy to think of how much was destroyed. 

Halfway through the bike tour we stopped for gelato at a shop where the owner makes his own gelato and serves the buontalenti cream flavor that is name for the original gelato of Florence. IT was GREAT gelato and we got there before the crowd so even better! 


After the bike tour we walked back over Ponte Vecchio (super old medieval bridge, now pedestrian only with jewelry shops lining it). Cosimo the 1st had a corridor built above this bridge so that he could walk from his office and first palace to his other, larger palace his wife requested that he build for her and their 11 children, without having to walk in the streets. Because of this, the meat market that had traditionally lined that bridge was forced out and goldsmiths brought in so he wouldn’t have to see/smell the animal remnants from his view. That corridor still exists and they are renovating it for tourists to walk through. We got a recommendation for lunch from our bike tour company and had a really nice leisurely lunch at Borgo Antico, in the Piazza Santo Spirito, while we waited for Matt/Tomi to finish their wine tour. I think this was only my second chicken/vegetables meal of the whole trip and it was delicious! 

Opinion of the tours: I really liked the bike tour, especially because we ended up being a small group and it was a way to see a good amount on a short time frame (and not walk the kids to death).  Having gelato halfway was a great way to bribe the kids to stay interested.

Matt & Tomi’s wine tour was MEH. It was very rushed because the company does two tours/day. They’d gone on the first tour so had to get back on time for their guides to do the second one. They were with about 10 other people, which was not a bad size, but said they felt like they were on a conveyor belt. They also ended up going to wineries super close to where we were staying so basically backtracked a good portion of what we’d just driven to get to Florence. HINDSIGHT: Booking a private driver/tour makes for a more relaxed and efficient experience. It was slightly more expensive to have the driver but he picked us up from our villa, is familiar with all the roads and good places to go, and you don’t feel rushed through your experience. All worth the extra $25/per person in my opinion. They did meet some fun people though and enjoyed a rooftop late lunch with them when they got back to town.

We met up with them for a gelato (the boys’ second of the day, #awesomeparentsweare, and to show them a couple of highlights of the city as we made our way back to the car.  And yes, the car was still there – phew!

More Gelato! (Squint and you’ll see part of the Duomo in the background)

Leaving Florence at 4pm put us in the mix of some pretty heavy traffic (another reason to have a driver) but we finally got back, had some down time and decided to order pizza delivery so that we could just chill at the villa and drink more of the wine we’d scored on our tours.


This was our last morning in Tuscany. We needed to pack up and head back to Rome so that we could check in to our hotel, return the rental car, and get Matt/Tomi COVID tested for their return flight. Our game plan was to hit up Orvieto on the way home so we could see one more city, grab a bite to eat, and then get back ASAP. 

Orvieto is crazy old, with ruins/tunnels from pre-Roman (Etruscan) days. It sits far up on a hilltop so the views are stunning (and strategic). There is another Duomo there that took 300 years to finish and these cute, tiny, winding, hilly, cobblestone streets you take to get to it from where we parked. It is smaller and quieter than any of the bigger cities we’d toured. Knowing we didn’t have a whole lot of time, we walked to the church, appreciated all the art/architecture on its exterior, then began the search for restaurants open for actual lunch at 12:30 (early for several of them, apparently!). We found a good spot, I had an amazing truffle risotto that I’ll remember forever, we had some fun people and stray cat watching, then walked back down the hill. Near our parking was an old overlook and area that led to a famous well built by Pope Clement VII while he was seeking refuge in Orvieto. We tried to find it only to realize it was its own tour type thing with admission tickets etc. We didn’t have the time so skipped it and got moving.

The drive to Rome felt long and the closer we got, the more stressful it was. There were several traffic incidents causing us to slow to a crawl but we made it in one piece to our hotel in Trastevere. We quickly unloaded so that Josh could start the arduous process of returning the car while the boys and I waited at the hotel and Matt/Tomi went out for the things they needed to do. 

Josh’s car rental return was a whole experience of its own. The G20 summit was going on in Rome the next day, so VIPs were apparently in town and meeting somewhere super close to this rental agency. When Josh finally got through rush hour traffic to get to the spot, he found it blocked off by soldiers. Long story short, he was able to get through after driving around several times (and I’m sure looking pretty suspicious!). Poor guy, at least the taxi ride back to our hotel was quick and easy. 

After a bit, we asked our hotel for dinner recommendations and based on that went to Tonarello. Our hotel said to me that it was the number 1 spot in the area even for local people, but I’m pretty sure the tourists have found out about it because it was busy! They make their own pasta and are known for their Roman dishes. While we were all getting pretty full of pizza and pasta we felt like we needed to go out with a bang and we were not disappointed. Luckily we went early (as he encouraged) and Romans eat a bit later, so we did not have to wait for a table inside (outside was packed with two-tops). The walk there was lively, but even more so on the way back. Bars, restaurants, musicians playing, it was a different vibe from the parts of Rome we’d been to at the beginning of our trip. 

Hard to capture the vibe on these old small streets in Trastevere

After getting the boys to bed, we capped off the night with Matt and Tomi  in the cute courtyard of our hotel, which used to be a botanical/herbal garden of a cloister. We reminisced about the ups and downs of the trip. What we hoped to do on other trips and just life in general. It was a great way to end the trip and we are so grateful they came over to Europe and took on this adventure with us. 


We met for a quick early breakfast at the hotel with our whole gang before going just the four of us to the airport (Matt and Tomi had a later flight). The travel home was uneventful and the cool, damp, windy weather of Maastricht welcomed us back home.

Last photo of the trip: Goodbye, Italy!

Josh, the boys, Melissa, and I leave again on Thursday for a trip to Avilés, Spain where Josh and I will compete in ITU Age Group Duathlon Worlds competition. I feel like my head is spinning from the laundry and the packing, but here we go! 

Make sure you check out Part 1 of our trip to Italy.


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