🌍 Travel: Italy Road Trip - Post 1 of 2 We Almost Died Three Times Before We Even Got to the Volcano (Summer 2024)

Naples to Sicily with a teenage son, a three-legged dog, and absolutely no margin for error

Our Southern Italy Road Trip. A woman, her son and their tripawd rescue dog

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There's a version of this story where everything goes smoothly. Where the GPS works, the weather holds, the rental car company is honest, and you arrive at your glamping tent to a glass of local wine and a sunset view instead of a lightning bolt hitting the fence six feet from your window.

That is not this story.

This is the story of a road trip from Naples to Sicily in the summer of 2024 that tried to kill us — or at least give us enough panic attacks to last a decade — before rewarding us with nine days on the slopes of Mt. Etna right as it erupted on the Fourth of July. Ash on the car. Ash on the terrace. Ash on everything. Happy Independence Day.

I'm telling you this because the travel content you see online is a lie by omission. Nobody shows you the cliff road that's falling apart under your tires. Nobody admits they double-paid for car insurance because a fast-talking counter agent in Naples got to them before they could think straight. Nobody posts the photo of the crate they had to order overnight on a volcanic island to get their dog onto a plane.

I have all of those stories. This is what the trip actually looked like.

First, We Almost Couldn't Leave Naples

My son Jovan flew in to meet me in Naples, Italy. I had been solo traveling since May — Rome, Pompeii, Sorrento, Procida (you can find a list of those posts here) — and now we were doing the southern leg together with Midnight, our three-legged rescue dog who has been hit by a car, survived surgery, and still manages to be the calmest member of our travel party. We stayed in Naples a few days and then headed to Ischia.

But first, and this is when I learned, that Booking.com doesn't do same-day taxi transfers, at least not at that time in that city (and from many experiences I've had after this, it's rare). We were stuck outside our Airbnb without a ride to the ferry. I put it off thinking I could book the same day. I don't know why I procrastinated. When I realized I couldn't book one, I started contacting all the people I had met while in Naples.

The driver that took me from Naples to Pompeii just a few weeks before while I was solo? He wasn't available until later in the evening (it was noon). The tour guide that took me through the mountains in Naples? He was tied up with tours. They were both really nice and concerned about me being stuck but they couldn't help at that moment and that last minute. I reached out to my previous Airbnb host. Thankfully, he came through. What a relief! He picked me up with my son and dog — phew! — and drove us to the ferry station. He told us they had never seen Naples be this busy so early in the season. Usually it starts later, he said. No wonder there were no same-day taxis.

The Italians' Favorite Island

First, I needed to drop off one suitcase. As usual, we had too many and too heavy. I had found a luggage storage right by the ferry station. Of course, people usually leave their luggage for only hours or maybe one overnight. I needed one week of peace and serenity— the week we would be in Ischia.

For luggage storage, the app I'm using while abroad is Bounce. You can also search "luggage storage" in Google, Apple Maps, or your favorite search engine to find all the options near you. If you're not seeing good results, try Google AI mode or any other AI search tool you prefer.

I had read up on Ischia — the island of the three where most Italians vacationed. As I had seen in the line to go to Procida, the island most visited by non-Italian tourists is Capri. In my search for a stay in Ischia, I found a hotel on Booking.com. Nothing on Airbnb that worked out.

The ferry ride was beautiful. Jovan was mesmerized by the ocean and the views of the coast and the mountains. We took the slower ride from Calata Porta di Massa — one and a half hours — as opposed to the faster hydrofoil route, which is only 50 minutes. This time, just like the taxi, I didn't prebook. I bought the tickets at the counter. It was SO hot. People kept coming up to us giving Midnight water. He was panting heavily. We sat in the shade and waited. It was a long while because we had just missed the last trip.

The ride itself was beautiful and enjoyable. But once we arrived, we had that movie moment. You know the one — the music is playing, you're loving life, happy as can be, and the record stops suddenly with a terrible scratching noise? That was exactly what it was like.

Welcome to Ischia. Passports, Please. (Just Yours.)

We got off the ferry along with everyone else, but we were the only ones who were stopped. About four or five men stopped us and asked for our passports. I was suspicious immediately — they had no uniforms. They didn't look official at all. I thought they were trying to rob us. I kept asking: why do you need our passports? And I pointed out that they hadn't stopped anyone else but us.

And then it came back to me instantly — we were the only brown people on that ferry. I had noticed it during the ride. It's typical, so as always, I shrugged my shoulders and kept on enjoying the scenery. But when they stopped only us, the realization I had made on the ferry came right back. How could I ever forget I'm brown and stand out in a ferry full — and I do mean full — of only very pasty people?

We went back and forth for a while. He told me not to worry about who he had or hadn't stopped. They wouldn't let us leave — or should I say enter the island — so I had to give them our passports. They made a phone call and gave our passport numbers to someone on the other end. We waited for quite a bit. They knew by my face — and as usual I expressed it — how disgusted I was with all of them. Had I seen this done to every passenger it would be no big deal. It was done only to us.

This of course took all the wonder and enjoyment out of the trip. I had no idea at the time what was going on in Italy with foreigners. Especially brown foreigners. Two years later and lots more travel on my timeline — I now know. I'm up to date and educated on just how disgustingly racist they are. Here's my post from just a couple of months ago while in Athens a second time, learning what is happening in Europe and their immigration policies:

Awakened Architect Part 1: The Death of the Bucket List — Why I'm Done With the "Tourist Dream"

Needless to say, I wasn't motivated to do much in Ischia. I stayed inside mostly working. I went on a hike. I went grocery shopping to cook, as usual, and I spent time on the grounds of the hotel reading, working, and just enjoying the quiet. The place was pretty and had a beautiful view — but you could only see it from the pool, as our room was tucked away in a corner. I literally booked that place while on the ferry. The host even had a happy hour, and I was not in the mood to attend. The way we were welcomed left such a bad taste in my mouth. So I did what introverts love to do most.

Retreat.

I must say the car rental there was easy, as the companies were online. There were three to choose from. They were prompt, on time, and professional.

I eventually found my peace there. But they made me work for it.

Rental Car Insurance Upsell

I had done what I thought was the responsible thing: I booked a rental car and added insurance through Booking.com before we arrived. It was already paid. It was already confirmed.

Then I got to the counter.

The agent was not friendly. He had the demeanor of a robot who'd been assigned to a job he resented. Again, the place was full of tourists. The only women there renting a car were with their husbands, who were doing all the talking and handling all transactions. It takes seconds to scan a room, and the main reason I notice these things so quickly is the stares I'm constantly getting. Most of the time I ignore it, because really, what am I gonna do? I just keep living my wonderful life. But it happens so much that every so often I look back at them like "did I just fall off a FREAKIN' alien ship?" — when all along, the kind of people that stare at me are the ones that look like aliens.

Back to the rental car rep — I've been wishing for some time that robots take over these jobs because these people are always miserable and out to ruin your vacation or whatever you're on. In my case, exploration. He sold me on car insurance. We had gone through so much already — getting stuck in Naples, finding someone to take us to the ferry, getting racially profiled in Ischia — that I actually forgot I had already purchased insurance through the online booking. I purchased it again like an idiot. Paying for double coverage.

I didn't realize until later — much later, the kind of later that involves a glass of wine and a long look at my credit card transactions online — that I had paid for the same coverage twice. The Booking.com insurance was sitting right there in my email. I knew I couldn't get my money back from the rental car company, so I contacted Booking.com asking why he would sell me more insurance when he clearly saw I already had it through the booking. They admitted to this being a common practice to extract as much money as possible from customers.

Aaarrgghhhh!!!!!

Booking.com graciously refunded me the insurance I had purchased with them, which was very kind. However, the insurance with the rental company was three times higher of course. Oh well. The damage was done. Lesson learned.

I want you to remember this moment when I tell you that in 2026 I can now reconstruct the exact coverage terms of any rental car policy I've ever signed, cross-reference it against my credit card protections, and identify a duplicate upsell within thirty seconds. Growth is expensive. Mine cost me double on car insurance in Naples. And this is not the only occasion in all the years of travel.

Ercolano: Vesuvius, Finally

Our first stop together was Ercolano, just south of Naples at the base of Mt. Vesuvius. For me this was unfinished business — during my solo trip, I had planned to climb the volcano from Pompeii and missed it because of an Italian national holiday that shut everything down. I wrote about that in the Pompeii post. Vesuvius had been watching me from a distance for weeks.

We went up. It was everything a dormant volcano should be — massive, silent, and completely indifferent to the small humans walking around its crater rim trying to comprehend what they were looking at. Midnight stayed in the apartment while Jovan and I stood at the edge of something that had buried an entire city alive.

Two weeks later I would be standing in ash again. Different volcano. Different story. Subscribe to read all about it.

The GPS Road That Was Trying to Kill Us

I booked two nights in Ercolano but we only stayed one. The second night was solely to go to Mt. Vesuvius for the day and take off in the afternoon to our next destination. We headed south into the mountains. I was done with the ocean. Our destination was Contrada Sant'Elia — a stone agriturismo in the mountains of Campania, hosted by a place called Ruralis, tucked so far into the hills that the host had specifically flagged in the listing: do not follow GPS onto the narrow mountain road.

We didn't follow the GPS onto the narrow mountain road.

Then we followed the GPS onto the narrow mountain road.

Here is what happens when you do this: you arrive in what feels like the right area, you can almost see the property, and then the GPS tells you to take one more turn. The turn leads to another turn. And then the road starts to narrow. And then it gets narrower. And then you realize you are on a single-lane cliff road above the Campanian mountains that appears to be actively disintegrating — no guardrails, crumbling edges, no room to turn around — and the only way forward is to keep going deeper into a situation that started as a wrong turn and is now something closer to a survival scenario.

Looking back, I had actually followed the host's instructions perfectly. So perfectly that before we took that wrong turn, we were only four minutes away from the place.

I was driving, of course. Jovan was 16 but because of our travels since 2022 had not gotten his license yet. He was in the passenger seat. Midnight was in the back, perfectly calm, watching the scenery like a dog on a road trip. Oh, and it was after 10pm.

The host, when we finally reached him by phone, responded with "nooooooooooooo!" — and that's when I panicked. He told us this road had been sending tourists to the wrong place for years. He had contacted Google Maps multiple times asking them to update the satellite data, which shows the road as functional when it has not been functional for a very long time. Google had not responded. The host asked if I would submit a correction request too, once we hadn't died and were safely at the property. I did. I now do not hesitate to report anything and everything to Google. I do it every time I encounter this problem, which is more often than you'd think. Satellite maps photograph roads from above. They don't know which ones are being held together with gravel and optimism. It could save a life. I've always been a "see something, say something" person because I've always been able to spot problems miles ahead.

So, about getting off that deadly cliff.

There was no room to turn around. The road had narrowed to the point where forward was no longer an option and reversing was the only exit — except reversing meant going backwards along a crumbling cliff edge in the dark with no guardrails. At some point in the mountain wall beside us there was a dark indent — a recess, a dent in the rock big enough to get the car into if we backed in far enough to redirect. We did not know what was in that recess. There was a large boulder at its edge. Behind the boulder, in the beam of our flashlight, was darkness that could have been a shallow pocket in the rock. Or a hole straight into the abyss inside the mountain, for all we knew.

Our phone was at 8% battery!!!

We used the flashlight. We inched backwards. We got the car turned around. I still don't know what was behind that boulder. I have decided not to think about it too carefully.

I don't go on narrow roads anymore. Not one more meter of pavement narrowing in front of me without turning around. The cliff road in Campania retired that habit permanently.

One more thing about technology on this trip: I have a Google Pixel. My son has an iPhone. In Europe and Southeast Asia, and parts of Türkiye, his iPhone has been largely decorative. The Pixel has kept us navigated, connected, and functional in every country we've been in. When I say the Pixel was the only reason we got off that cliff — I mean it literally. It was the only phone with a signal strong enough to reach the host, and the flashlight that got us turned around on 8% battery before the screen went dark.

Contrada Sant'Elia: Seven Days of Stone and Silence

We made it to Contrada Sant'Elia. The property was extraordinary — ancient stone walls, mountain silence, the kind of place that makes you understand why people settled in difficult terrain and never left. We stayed seven days. We needed all of them to decompress from the cliff road.

It was pure serenity. The owner had built a forest for bathing, borrowed from the Japanese forest bathing culture, and he provided a guide on how to experience it properly. It was amazing. We also had a jacuzzi tub on our patio. On the grass. Midnight, Jovan, and I enjoyed every minute of sunlight, mountain breeze, and jacuzzi soaks possible. Along with bottles of wine and Italian cookies and snacks. It was peace we very much needed. We only ate out once when we arrived — at a family-owned restaurant with really great food. But I wanted to cook the rest of the time. I usually do when I travel with my son because he eats like there's no tomorrow. He's a personal trainer now who has meticulously built every inch of his body in bodybuilder style. He's done a great job and now he trains others — it's his current career of choice.

Campodorato: One Night, One Lightning Strike

After Sant'Elia, we drove to Campodorato for a single night of glamping — bell tents in an olive grove, string lights along the stone path, a fire circle below the trees. The kind of place that exists in the space between camping and something you'd describe to someone who's never understood why people camp.

We had stopped at a small grocery store at the base of the mountain — the last one for miles — to stock up before heading up. Once again, we reached the nearest street of the property and once again we turned around. The next turn was onto a small mountain road, and being traumatized by the events of the week before, I was afraid to end up on another non-working road on the side of yet another cliff. We drove around trying to find it. The sky had turned the particular shade of grey that precedes something serious. Cell connection was terrible, as it had been pretty much the entire time in Italy. We stopped somewhere where we had service, and while looking at the map on my phone inside the car, lightning hit the fence.

Not near the fence. The fence. The metal fence approximately four feet from where we were sitting in a hybrid vehicle, which I suspected was more susceptible to lightning — as in, attracting it. Someone I asked later said this is true. I didn't research it, so don't come for me if you find out differently.

Midnight did nothing. He is not moved by lightning. He is, however, completely undone by the thunder that comes after, and by loud street traffic — in apartments, he finds the bathroom and does not come out until silence returns. He is missing his front left leg from being hit by a car as a puppy, before we adopted him. I suppose his noise phobia stems from that. Another thing about Midnight from that traumatic event: he has been poked, prodded, and treated for more things than most animals survive, and as a result he lets us do anything medical without resistance. They're so innocent and vulnerable.

I didn't hear a beep from him when lightning hit the fence, but my window was only slightly open — it was sprinkling and hot — just enough for me to hear and witness the strike up close.

Later that evening we ate a beautiful dinner outside. Midnight was right next to us. It was raining hard so we had to move inside. We enjoyed the swing on the property and all the beautiful outdoor decor they had obviously put a great deal of time into. Jovan was ecstatic with the food, of course.

We had one night. We had a wonderful breakfast and excellent coffee outside the next morning. The hostess' father, who had helped her build the place into what it was, fell in love with Midnight. He wouldn't stop talking to him the entire morning and all the way to the car, saying goodbye to the dog as we left.

Both mountain stays were great experiences. Unique, peaceful, and serene — despite the near-death experiences getting there.

We crossed the Strait of Messina a few days later. Sicily was waiting. So was an erupting volcano, an impossible dog crate hunt, and a rental car I left at the curb with the keys inside.

That's Post 2. Subscribe so you don't miss it.

You can watch my video about all this in my You Tube channel:

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