We arrived in Gubbio from Monte Sant Angelo and spent our first morning exploring—the main palazzo in the town square, a Leonardo da Vinci exhibit displaying many of his inventions, and finally a ride up the mountain behind Gubbio on the funivia from the parking lot at the edge of the small medieval town to the top of the mountain looming over it to see the views of the town with the Apennines in the distance. By the time we got back to town, we were hungry and craving pizza, which we’d had surprisingly little of since landing in Italy.

We tucked ourselves into a tiny table in the back of a very crowded osteria. The place was buzzing with locals on their lunch break—not a single tourist—which I knew was a good sign. We ordered two pizzas, porcini mushroom for me and margherita for David. I no longer asked what size a pizza would be in Italy—after years of asking, I knew that the answer would be normale, and that a pizza served in Italy was generally around 14 inches in diameter and was intended for one person.

I had spent so much time in Rome prior to this trip that I was used to the very thin and crunchy crust of Roman pizza, but I was learning that pretty much everyone in Southern Italy preferred pizza Napoletana, which has a puffy, soft outer crust, with very thin and soft crust in the center. I finally understood why Italians ate pizza with a knife and fork—it was simply too soft and floppy to pick up a slice to eat.

It wasn’t, however, too soft to crack dental work.

David had spent the past year dealing with tooth extractions, implants, braces, and bridges. His dentist had rushed to get his new front permanent bridge done in time for our trip, and it looked lovely. But the porcelain material must have been flawed because the two-week old “permanent” bridge cracked right in half in the front of his mouth on the first bite of his very soft pizza. Luckily, he didn’t swallow the porcelain pieces, which I wiped off and put into my purse.

We quickly finished our lunch, then went straight to the hotel to ask for help. Gubbio is a small town, and like all the other small towns in Italy, everything was closed in the afternoon. We were scheduled to leave first thing in the morning, and I was in a panic. I explained the situation to the owner of our hotel who called her personal dentist, and he agreed to see us later in the afternoon—after he finished his lunch.

Medical emergencies in a foreign country were, unfortunately, not new to me. When my late husband collapsed on vacation in Madrid, I spent two months there while he was in a coma. It had been incredibly difficult to work through that situation—in addition to the obvious stress from his critical medical condition, I was far from home and negotiating a medical system I wasn’t comfortable with. I knew nothing about brain aneurysms or cerebral hemorrhages, leaving me questioning the treatment plan. I didn’t speak Spanish, which was a huge handicap. The doctors in Spain, at least the older and more experienced ones I trusted the most, only spoke Spanish, and I was never certain the younger interns were translating correctly for me.

After that experience, I vowed to be more prepared so that I could be more in control in an emergency situation, and I had arrived in Italy fully prepped. David had developed epilepsy a few years earlier after a car had rear ended him, and just months before our trip he had suffered a very bad cluster of seizures that landed him in the hospital. The doctors had adjusted his medications after that and asked him not to drive for a few months to be sure his seizures were under control. Worried something might happen while we were in Italy, I had prepared a short conversation should I need to explain this to anyone.

Il mio compagno ha avuto un incidente con la sua macchina. My Italian notes went on to explain that the car accident had caused a lesion in his brain that had resulted in epilepsy. I had described in Italian what his seizures were like and what medications he took just in case he would need medical attention. I researched where the closest hospitals to Rionero were in case I needed to take him for treatment. I made sure I had all his doctor information on hand before we left and copies of his medical insurance. I was prepared for the worst and, unlike in Spain, I could speak Italian. I knew that if he had an epileptic emergency that I’d be able to navigate his care in Italy. But it never occurred to me that I’d need to navigate care for him because of a dental emergency.

While David sipped on a neat glass of whiskey (it was only 2:00 in the afternoon so I took this as a sign that he was agitated even though he was trying to act like this was no big deal), I flipped through the translator on my phone to make sure I understood enough words to speak to the dentist. At 4:00 we walked to his office and took a seat inside.

When the dentist peaked his head out, I said, “Abbiamo un appuntamento. Quest’e’ David.” He nodded hello and his assistant took us both into the back. I had intended to wait out front, but neither of them spoke any English, so I needed to translate. I explained to the dentist how he had broken the bridge as I pulled the small broken pieces out of my purse.

We were hoping he would make a new temporary bridge, but it was late in the afternoon, and I could tell he didn’t want to attempt that. Instead, he told us he could only glue these pieces back on. He made sure we knew this was just a temporary fix—obviously, I thought—and then he got to work. I was worried this wasn’t going to hold, so I asked him how long he felt this would last. While I didn’t fully understand his answer, it was something like “your guess is as good as mine, and probably not very long.” Great. Not the answer we wanted. We still had six weeks left in Italy.

We left the dentist’s office and went straight to our hotel room to call David’s dentist in Denver. He was horrified to hear what had happened and said his staff would make a new temporary bridge that day and ship it overnight so it would be waiting for us when we got back to Rionero the following week. I sent a text to Maria explaining what had happened and asked her to make an appointment with the dentist in Rionero for the following Friday so he could remove the broken bridge and install the new temporary one.

For the next week, I spent at least an hour every day trying to track the FedEx shipment, both online and on phone calls, arguing in Italian with the agents. Overnight, it turned out, just meant it left the US and arrived in Europe overnight. But actually getting the package delivered, I was learning, was going to be a challenge. First it bounced around Europe before finally arriving in Italy. Then once it was in Italy it was held up in customs. FedEx eventually confirmed customs had released the package, but after a couple of days I discovered that was wrong. FedEx referred me to their customs agency that clears medical shipments, who said they needed a full accounting of what was in the package so they could release it. Days later it was still being held hostage, and when we arrived back in Rionero we were forced to cancel the appointment with Maria’s dentist.

Despite my improved language skills, despite my valiant efforts to track the package, despite all my hard work, so far, I had failed. Despite Italy’s reputation for being somewhat bureaucratic, I thought I would have more in control in a situation like this. Clearly I didn’t.

Another full week later, the bridge had still not been delivered. The FedEx site showed it was in Reggia Calabria, the region south of Basilicata, and was out for delivery, which made no sense to us since this was hours away from us. With little faith that we had any idea where the package really was, we decided to continue our adventure and not let the situation deter us. David really didn’t want his bridge to be the reason we missed anything we had planned to see or do on this trip. He was eating carefully so as not to irritate the tooth that was only partially covered with broken pieces of porcelain, so we both figured it would be fine.

We departed for our next excursion a day trip to Alberobello and Monopoli before spending the night at the airport in Bari to fly to Sicilia early the next morning. As we ate dinner at the airport hotel that evening, I checked on the shipment. The FedEx site showed the package was now in Rome, but honestly, we didn’t believe anything at this point, so we flew to Sicilia as planned very early the next morning.

We spent the first three nights in Palermo, visiting historic sites, eating arancine, climbing to the top of churches for the views, and shopping at the incredible markets in the centro storico. David’s mouth was holding up and we were thinking maybe he’d be lucky enough to get through our time in Italy and back to Denver before having to deal with the removal of the broken bridge and the installation of the new one. He was having a bit of sporadic pain that he was managing with Tylenol, so it didn’t seem like there was anything that needed to be addressed right away.

After Palermo, we drove west to the pretty town of Trapani on the northwest coast of the island. During our first breakfast I could tell David didn’t feel well. His pain had increased significantly since the day before, radiating up from the front area of his mouth into his face next to his nose. While I’m not a trained medical professional, I knew this was probably a sign of an infection since the tooth had been exposed for some time now. David wanted to continue with our plans for the day, but I insisted he needed to see a dentist before we went anywhere. But who? Here we were again in a small town and surely everything would be closed for most of the day. Despite all my preparations for this trip, I didn’t even know where to start to get him the care he needed.

There was a man with a cable knit fishing sweater who we had seen hanging around the front desk of our hotel chain smoking. We couldn’t tell if he owned the place, worked there, or just liked to talk to his friends all day, but when he overheard us discussing the need for a dentist, he was quick to offer his help. He asked if we knew there was going to be a dental meeting right here in our breakfast room at the hotel this very evening. No we did not, we told him. While he left to call his personal dentist, I joked with David that he should just show up and see if one of these twenty professionals could help. He could be the subject for a panel discussion about bridges and porcelain failures. I wasn’t sure David saw the humor in that, so I was relieved when the man returned and told us we had an appointment in 45 minutes.

Twice now this had happened. Someone called their personal dentist who agreed to see David right away. I’ve had medical “emergencies” in Denver that required a month-long wait for an appointment. These Italian dentists weren’t rushing to see David because he was their patient, but because someone had asked them for a personal favor. They certainly weren’t rushing to see us because of the fees. The last visit had only cost forty euros. I can’t even talk to my dentist for less than $100, let alone get emergency treatment. Italy may have its challenges with bureaucracy, but Italians, it seemed, had their ways around that.

I had experienced the kindness of strangers like this in Spain while my husband was hospitalized. A friend of a friend in Denver who lived in Madrid had taken me to lunch and done my laundry. An old college friend of my friend’s cousin had offered legal advice and helped navigate the hospital system. A colleague of a high school friend of my husband’s had worked the system to get me medical records. The situation in Spain had been largely out of my control, and I had accepted that. Why did I think an emergency in Italy would be any different? What made me think I could control this any more than I had been able to control the emergency in Spain?

When we entered the dentist’s office I went through the story once again, explaining that we had been waiting for a temporary bridge, but that it hadn’t arrived. He X-rayed David’s mouth and told us he thought there was an infection, so he was prescribing an antibiotic. Before leaving he kept explaining to David—in Italian with me translating—that this was very serious, that he really needed to get this fixed, that he should wear a mask so that the cold air didn’t irritate his tooth, that he should not bite on this tooth at all. This all seemed obvious to me, but I kept my mouth shut while David assured him he’d follow all these instructions.

With antibiotics and plenty of Tylenol, David was ready to enjoy the rest of our time in Sicilia. After the dentist, we hiked around the town of Erice, another one of the Borghi più Belli d’Italia spots, snapped photos of Trapani from high on the hill, and watched the sunset over the island just off the coast. We were enjoying a glass of wine in the hotel lobby before dinner when David’s dentist walked in for the evening dental meeting. He approached us immediately and shook David’s hand quite heartily. “Come stai?” he asked, clearly worried about David’s condition. David assured him he was feeling fine and that he was doing everything he had been told. The dentist smiled with relief, then excused himself—it turned out that he was the keynote speaker for that evening’s dental meeting in our breakfast room, and he needed to prepare his remarks.

The next day we went for a wine tasting at DonnaFugata in nearby Marsala. Over the course of two hours we learned about Sicilian wines and enjoyed a tasting with lunch. As the driver, I merely sipped and spit, but David fully enjoyed the five glasses of wine our host Antonio poured. Whether the antibiotics or the wine were doing the work was debatable, but David was finally pain free.

We had planned to hike around the ruins at Segesta before returning to the airport in Palermo, but we were getting on each other’s nerves driving to the site, arguing about where to park and how to enter the site. I was trying to be patient—not my strong suit—knowing David—never one to complain—was probably suffering more than he was telling me.

We were still hoping that by the time we returned to Rionero on Friday the FedEx package might finally arrive and David would be able to see the dentist instead of waiting through the weekend. As I whipped the car into the parking area of Segesta, my phone pinged with a text from Stefano. The bridge had finally arrived in Rionero, and his father had it in their apartment. His mother had made an appointment with the dentist for 4:00 the following afternoon. It had taken three full weeks for David’s “overnight” package to arrive, but by Friday evening David would finally get the new temporary bridge installed, which I was certain would make our last three weeks in Italy more enjoyable.

The flight from Palermo to Bari was very early in the morning, but uneventful. I drove our new rental car from the flat coastal area around Bari into the rolling green hills dotted with windmills cutting through the farms of Basilicata. I’d grown to love this landscape over the last few weeks, and I felt like we were returning home as I drove to Rionero. David slept for the entire drive, exhausted from dental pain, hiking in Segesta, and the early flight out of Palermo.

Shortly before 4:00 we walked toward the “financial district” in Rionero—what we had come to call the main street leading to the train station because it was home to the three banks in town—and cut down the alley to the dentist’s office. The assistant let us in, and we sat down to wait. Surely David was going to be the last patient of the day. But as we waited, another woman came in. I listened to her explain that she didn’t have an appointment but that she had a bad toothache. No problem they told her, just come back in an hour. I was pretty sure in Denver I would have been told to go to an urgent care facility because the dentist had no intention of staying longer at work on a Friday evening.

I went into the exam room with David and began explaining the history of his case to the dentist as I handed him the new temporary bridge. “Penso che il materiale era scadente e il ponte fallì,” I explained, wanting him to know that David hadn’t caused this, but rather the porcelain itself had failed. He responded with something very close to “ya think so?” in Italian making me feel a little silly.

He then started to remove the broken “permanent” bridge. It sounded like he was using a sledgehammer to crack it off, and I adjusted my seat so I could get a better view. He was using some ancient device to repeatedly crack away at it, and it looked barbaric. David kept tensing his legs and feet, clearly uncomfortable—the dentist hadn’t given him any painkiller. I watched this torture for 22 minutes before the dentist swore loudly. He had cracked off David’s front tooth as he was working to remove the final bits of porcelain.

I wanted to scream, but sat quietly, hoping he had a solution. He kept moving in and out of the room, talking to his assistant, who I now understood was his wife, about where they should have dinner, and poking around in David’s mouth. He seemed like he was on a mission, so I didn’t interrupt.

Twenty minutes later, he pressed the new temporary bridge, which he’d had to partially remake to cover the broken tooth, into David’s mouth. Then in rapid fire Italian he made sure I understood this was only temporary and that David really needed to see a dentist when he returned to Denver. I wanted to say “ya think so?” but instead said, “Grazie mille dottore.”

David was in pain from the hammering on his mouth and I was in pain from watching, so we left the dentist and went straight to Alter Ego for Francesca to make us an old fashioned. “Singola o doppia?” she asked reaching for the Woodford bourbon.

“Most definitely a double today,” David told her.