From Flat Tire Chaos to Tuscan Dreamland

Date: November 22
Location: Taormina, Pisa, Castelmuzio
Weather: 65 and sunny (Taormina), 45 and partly cloudy (Pisa), 36 and cloudy (Castelmuzio)

“We have a flat tire.”

Not exactly the words you want to hear from the friends driving you to the airport.

The plan was simple: Carlotta and Marta would bring the car up from the parking garage – a bit of a walk – and we’d leave around 10am. But as soon as they reached the garage, they discovered the tire was flat. Carlotta called me at 9:30am.

“Hi, we have flat tire. But don’t worry – I will find you transportation, a taxi or something. We called the assistance line for the rental, but no answer.”

I hung up and Carla asked, “What’s up?”

“Well… they have a flat tire.”

We looked at each other and started laughing. We have a long history of laughing at the worst possible moments – and honestly, it’s all part of the adventure. Plus, we had complete faith that these two would figure it out.

We kept packing, and around 9:50am I said, “Let’s take our bags down now.” Either we’d be out in the street trying to flag down a taxi (which we hadn’t seen once in this ancient village), or Carlotta and Marta would appear like magic.

The moment we stepped outside, my phone rang.

“Hi Lisa, good news – the tire is fixed and we are five minutes away.”

I checked my watch: 9:55am. Of course. These two are a well-oiled machine. They always deliver.

The next challenge was fitting our luggage into their tiny car. But again – they found a Jenga-level solution and off we went to the airport.

I asked how on earth they fixed the tire. Carlotta explained:

First, they drove – on the flat – to a gas station, but it was closed. Then she thought, “Where can I find a bunch of men standing around doing nothing who can help?” Naturally, the bus terminal. Sure enough, it was full of men ready to jump in. She used the “I am old, I don’t know what to do” line… and they practically lined up to assist. They even had the equipment that fills the tire with sealing foam, so within minutes the car was road-ready again.

I again marveled at how seamlessly those two operate: tolls, phone calls, directions, navigating chaos – they’re like Olympic figure skaters executing a perfect routine. They glide through it all.

Check-in at Catania Airport was shockingly easy. No lines, no security wait. Carla’s bags were over 40 kilos, and Ryanair is notoriously strict, but they didn’t charge a thing – just waved everything onto the belt.

After finding our gate, we grabbed coffee and sandwiches – thank goodness, because it ended up being our only meal until 8pm. We had no idea a full travel marathon was ahead of us.

Ryanair is the Spirit Airlines of Italy… only more bare bones. Everything is an add-on. The seats look like they’re made of cardboard, and the safety instructions are decals stuck to the seatbacks – no pockets, no pamphlets. Honestly, though? Probably the most useful safety display I’ve ever seen. When the food and beverage cart rolled by without stopping, we figured you had to prepay for everything, even water.

It was only an hour and ten minutes – we would survive. Carla produced two peppermints she’d pilfered at LAX, and that was our in-flight dining experience.

The plane landed on time, and luggage came out immediately – only four bags total for the entire flight. It felt like a commuter hop.

We waited 20 minutes in the cold Pisa air for the shuttle to the rental car facility. I’d chosen a local rental company instead of Hertz, on the advice of Italian friends who “know people” and can help if something goes wrong. At the counter they offered an upgrade from a Fiat to a bigger SUV, but in Italy that’s the last thing I want. I prefer not to wedge myself between two medieval stone walls just trying to park.

They handed us a bright siren-red car – no one would miss us on the road.

It took seven minutes to drive to the parking lot for the Leaning Tower of Pisa, and another five minutes to walk to the site. No crowds whatsoever this time of year. The usual souvenir stands lined the walls, but once you step through them, the sight of the tower and surrounding buildings is still breathtaking.

We did our cheesy “holding up the tower” photos and wandered around in the gold light of sunset. Puffy pink clouds floated above – impossible to capture properly in photos.

As we headed back, I realized I needed a bathroom. This is always the Italian dilemma: bathrooms are scarce, usually require a café purchase, and toilet paper is optional. I found a café, but the line for the toilet was ten people deep. We had a 2.5-hour drive ahead to the villa in Tuscany, it was getting late, and stopping meant arriving late for dinner. But realistically… we were going to be late.

An hour in, I pulled off at a gas station – and hallelujah – clean, empty bathrooms. Carla didn’t have toilet paper, but I’d lucked out, so I “spared a square” (actually several), and off we went again.

We arrived at La Moscadella around 7:40pm. Pulling into the gravel parking lot felt like coming home. The setting is spectacular. Everyone had already arrived and was seated – it felt like a grand reunion.

I tried to ignore the table of 20 nearby, half of them children, plus another table with three more. I love kids – but some parents often don’t manage them well in fine-dining settings. You don’t want your elegant Tuscan dinner to sound like a night at Chuck E. Cheese. When all the kids left the dining room afterward, the difference was immediate. I made a mental note to strategize with Isabella about future meals.

Dinner was several courses – wonderful but abundant. I’m halfway through my trip, the richness is catching up to me, so I limited myself to half portions of everything. Everything was delicious, but I need to pace myself if I’m going to survive until Saturday.

After dinner, Carla and I tried to find the parking for our villa in Castelmuzio. Since it’s a hilltown, parking is below the village, but I had no idea where – and the concierge was gone. I think they assumed that because I’ve been here many times, I knew. I did not. Eventually I gave up and parked outside the village, and poor Carla (with a bursting bladder) walked the ten minutes with me in the crisp night air.

Thankfully, our visible bags had already been brought to the villa during dinner. Our upstairs rooms look like they were lifted straight from a “Live Your Tuscan Dream” catalog. We chatted, unpacked, and I finally went to our rooms at 1:30am… feeling wide awake.

What is with this time-zone adjustment? They say it takes one day per hour – and I am living that rule. At this point I’m so deep into a sleep deficit I doubt I’ll catch up on this trip. But somehow, it all works. Sleep-deprived but soul-thriving.