Messed Up In Italy: A Unique Comedy of Errors

2 bumbling travelers who messed up in Italy

Confessions of a Bumbling Travel Novice

Who has a fear of traveling overseas and screwing it up? Plus, is actually crazy enough to go with only their 19-year-old daughter as a guide? Me, that’s who!

And I messed up, big time! It was the two stooges in Italy!

But, I get ahead of myself! Let me start at the beginning.

This is a story you want to hear!

Two Bumbling Travel Novices Decide To Take A Really Big Trip

As it happens, I was working from home one day and noticed an email come across my cell phone. It was another travel deal from So, I picked it up.

“Hey, you want to go to Italy?” I asked my daughter, Faith. The deal was less than $1000 each, over a week, for two people, flight, hotel, and rental car included.

“Sure.” My baby girl answered.

Of course, I booked the trip then and there before she had a chance to change her mind. Not to worry! My girl is an adventurer like her momma.

In less than one minute, my mini-me and I were headed to Italy!

How To Prepare For A Trip To Italy

When doing travel research, I learned that Italy is an ancient country with few elevators. The country nourishes its cultural and architectural heritage, maintaining the buildings built by its ancestors centuries ago.

Then I read the Duomo in Florence, one of the places I wanted to go, contained 463 excruciating steps to the heavens. Thus, my out-of-shape self and my daughter headed to the gym. Over the next three months, we worked on building stamina via the treadmill and stair-stepper.

And thank the Lord, we did.

Also, using a translation app on my phone, I spent an hour each day teaching myself just enough Italian to get into trouble. I wanted to be able to ask for help or directions if needed.

My research informed me that Italy’s biggest issue in the area of crime was the vast array of pickpockets waiting to assault unsuspecting pockets and handbags.

No problem, right? There’s no way I would later say that I messed up in Italy. Since I was so well prepared!


We’re On Our Way!

The big day soon arrived. After a 16-hour flight with a brief layover at London’s Heathrow Airport, we arrived in Rome.

Getting our luggage and going through customs was no big deal, and we found our rental car without issue.

From there, it was all downhill.

The tiny car, as are all vehicles in environmentally conscious Italy, was about as long as our suitcases. Of course, it was a stick shift. (Which I hadn’t driven in years.)

I Might Have Messed Up On The Way To the Hotel

On the way out of the airport, we immediately entered a roundabout where I promptly nearly took out two Italian drivers. Horns were blaring, but I was too focused on not getting lost, to notice.

In my defense, it was dark, and I had just gotten off a long flight. Plus, I had a three-hour drive in a foreign country, in the dark, ahead of me. I had preset GPS on my phone back at the airport, where Wi-Fi was available. Our portable Wi-Fi system was to be delivered to the hotel.

We were starving. Did you know the food on planes is sometimes nasty?

On the way to our 12th-century castle, turned hotel, in Tuscany, we spotted a place off the autobahn (freeway) that looked like a restaurant.

It was not. The inviting restaurant turned out to be an auto parts store in a sketchy part of town. However, I had already pulled into a parking spot in front of the building.

And couldn’t find the reverse gear to back out.

Faith looked at me. “What are we going to do?” She asked, eyes wide and anxious.

It would not be the last time she would ask me this question.

So, I assessed our tiny go-cart, I mean car. Next, I put the gear in neutral, got out, and pushed the wee bit of fiberglass and metal out of the parking spot.

But, it kept going. Straight toward a group of people and some parked cars nearby.

Faith was still in the passenger seat. Her face said it all. Without hesitating, I dashed around, jumped into the driver’s seat, hit the brake, then the accelerator, and then first gear. Finally, we sped out, leaving rubber behind.

Yes, I had messed up again! Sheesh!

Consequently, we decided not to stop again, but I did take a wrong turn and ended up in a desolate area, on a two-lane road. Mistakenly, I tried to turn around. But, as I still couldn’t find the reverse, we got stuck sideways across the road.

Unfortuneately, we then looked up to find a long row of vehicles lined up on both sides of our car, impatiently waiting for us to get out of their way. A lovely, Italian man stepped up to help us.

As I used many hand gestures and tried to explain in my limited Italian, the man said something in Italian, got into the car, and began to drive.

Thinking he was stealing our vehicle with all of our luggage, passports, and money, we chased him a short distance down the road. Thankfully, he pulled the car over and stopped, allowing the other drivers to resume their journey.

Where’s Our Hotel?

However, our castle did not seem to be where the GPS said it would be. We were in the middle of nowhere, and of course, the area was rural and deserted.

Once again, I turned around, and an exact, identical experience of the earlier turnaround attempt repeated itself.

Those Italian drivers can come out of nowhere.

On our third circle back, Faith spotted what appeared to be an alley between a gap in the trees. It was a deeply rutted, dirt lane. As we traveled along this bumpy roadway, she spotted a crude, wooden sign announcing the presence of our castle-turned-hotel.

We had arrived!

Where Is Everybody?

By now, it was eleven o’clock at night, and lighting was limited. Not a soul was around. In the eerie quiet, late at night, in the presence of a looming castle in a foreign country, Faith turned again to look at me.

“What are we going to do?” She asked.

With teeth gritted, I informed her that we had paid to spend the night here and we were going to spend the night! Dragging our luggage behind us, we set off to search the area.

Painted frescos on hotel walls in Italy

The painted frescoes on the ceiling and walls in our honeymoon suite

painted frescoes in Italian hotel room

Thankfully, after passing through a private courtyard, we happened upon a huge, wooden curved door in the wall. And to our not bright and un-shining eyes, an old-fashioned, brass key rested in the lock.

“See,” I told my fatigued, weary daughter. “They knew we were coming, and they left this key here for us.”

Living Like Queens In A Castle Is Not Messed Up

Indeed, Faith and I entered the most elaborate apartment we had ever seen. It was as big as our house back home, and it had a spiral staircase leading upstairs! Gorgeous hand-painted frescoes were on the walls and ceiling.

It was fabulous! Except for one thing!

Even though it was the last day of February, there was no heat. Thus, it was icy cold!

So, road-weary and feeling dirty, we decided to take a nice shower. However, there was no warm water either, so we decided to remain dirty for a while longer.

Thankfully, I found five wool blankets in a humongous armoire, and we covered one of the beds with them. Before finally falling asleep, my daughter asked me the question that had already been mulled over in my mind.

“What if we wake up in the morning and there are men with machine guns all around us thinking we stole this room?”

“Nonsense!” I told her. “I paid for this room. Now, let’s get some sleep!”

Eventually, morning came, and we were awakened by the sound of birds singing. Happily, I threw open the wooden shutters and saw charming scenery that took my breath away!

“Welcome to Italy.” The gorgeous, foggy countryside seemed to say.

First View of Tuscany

Our First View of Tuscany From The Honeymoon Suite Window

Welcome To Italy Novice Travelers!

Faith and I dressed and headed to the office, where we found hotel employees who spoke excellent English. (Most everyone in Italy knows at least a little bit of English.) There, we were informed the apartment we had overtaken, was the honeymoon suite which had been shown to a prospective couple the day before.

As if apologizing, the hotel employee told us, “Someone must have accidentally left the key in the lock. We don’t even have the heat turned on in that part of the building.”

“No kidding,” I responded.

Our First Morning In Italy-Tuscany

After being shown to our new salon, (with which we were quite impressed), Faith and I showered and dressed for the day. Then, we headed to the hotel’s cafe for breakfast and encountered a nice surprise.

Two couples were in the tiny cafe, dining together. Being American, we all noticed each other. “We’re from Grand Prairie,” they said, which was only five hours from where Faith and I live. One of the couples even had a daughter who attended college in our city!

Needless to say, we spent an hour with the two couples, laughing and sharing travel stories. Thankfully, one of the men told me how to find the reverse on our little car. Regrettably, it was their last day in Italy, and they were headed back home.

However, our lively conversation came to an end when we heard screaming and noticed an elderly man at a nearby table putting his hands over his ears and pitching a fit.

Apparently, we Americans were being too loud.

So, we said goodbye to our friends who were vacationing on the same travel package as Faith and me.

Driving Through Tuscany

Faith and I pulled out of the parking space with no further trouble. Hence, we spent the day driving through Tuscany and fell in love with the beautiful, rolling hills, amazing olive and grape groves, cypress trees, and ancient buildings.

Personally, the atmosphere took my breath away.

Significantly, Faith was most impressed by the fact that at age 19, she could legally drink wine.

We enjoyed a wonderful lunch at an outdoor cafe. I don’t remember the name of the town, but we enjoyed the locals who stopped by and talked to us.

Later, Faith and I ended the day in Sienna, with gelato and a visit to the most gorgeous cathedral I have ever seen.

But, I have to say my favorite town was San Gimignano, a medieval, walled, hilltop city with 14 towers, charming shops, bakeries, and restaurants.

A charming terrace in San Gimignano

A beautiful lookout in San Gimignano, Tuscany. There was no gaffe made by coming here.

Adventures Of Two Bumbling Novices in Florence, Italy

Day Two was spent in Florence, the capital of Tuscany. Florence is a beautiful city where Leonardo Da Vinci spent most of his life. In fact, Florence is known as the art capital of the world. While there, we visited its beautiful cathedral, the ancient bridge, Ponte Vecchio, with its many shops, and the San Lorenzo Market and Mercato Centrale.

However, the highlight was the stunning, very large, and lifelike Statue of David, completed by Michelangelo, in 1500. You can see the veins running through his arms, the muscle tone throughout his body, and even the expression on his face. In case you are interested, David can be found in the Galleria dell’Accademia.

Faith had to have a close-up video of David, but for modesty and dignity, I will not be showing her video here.

Thus, I will say all of the art at the cathedral and various museums was amazing! Many of the paintings go back through the ages. The oldest I found dates to the 1300s.

And, the Duomo with 463 steps that we worked so hard to be able to climb? Didn’t get to see it. All tours were filled up for the day, and I had not pre-booked.

Yes, I messed up again!

Fun In Venice

The next day we were up at dawn to catch the train to Venice. It was rainy and cold, and we loved it. The city on the water is the place of dreams!

Of course, we rode a gondola and since I’m a little larger than my daughter, my side of the gondola kept dipping toward the water. “Lady, lady,” The gondolier kept admonishing me, “Scoot back to your side.”

“But I’m afraid I’ll fall into the water,” I whined.

“Lady,” he said in his frustrated, Italian accent, “It’s only a foot deep!” I’m guessing it’s not a big deal if a tourist falls into the icky water!

However, it was all good as we got to see Leonardo Da Vinci’s house, which was crumbling but beautiful.

We also had a wonderful time eating lunch at another outdoor cafe on Canal Grande. The cute, little Sicilian server asked Faith on a date, but too bad, we had to get back to our hotel that evening.

After a heavenly day (I didn’t mention it was Carnival, and lots of people were dressed in elaborate costumes), Faith and I set out to find the train station. We had a two-hour return trip ahead of us. After a few minutes, we realized we were lost.

At that point, I stopped to ask an Italian gentleman how to get to the train station. His wife, nearby, thought he needed help giving directions. While they passionately argued about how to advise us, Faith and I snuck off and found our destination one block away.

In the Florence train station, we ate the best McDonald’s quarter pounder that I’d ever eaten before we made it back to our castle around eleven o’clock.

Dancing in Venice With a statue

Faith found someone to dance with in Venice.

Fabulous Cinque Terre

The next day, I took a two-and-a-half-hour train ride to Cinque Terre, a fabulous Italian national park on the cliffs of the Ligurian Sea. Five colorful and picturesque villages live there, and scenic hiking trails are abundant.

As the day before had been cold and rainy, we wore cool weather clothes and big coats.

It was 100 degrees.

Seemingly, Italian weather is similar to West Texas weather, where you can experience several seasons in one day!

Nevertheless, Faith and I thoroughly enjoyed our hike from one village to another on the rocky trail. Because of the traveling stamina, we had acquired, we were able to see four of the five villages. We left Vernazza, a small town with a nude beach, off of our itinerary.

Surprisingly, we made it safely back to our hotel around eleven o’clock without a single gaffe!

A Magical Day in Pisa With A Very Big Gaffe

As Pisa was slightly less than an hour and a half away, we decided to drive. While speeding along with the other vehicles on the autobahn, I happily thought no police car would be able to pull over speeders since no shoulders were present on the road.

This was our last day in Italy, and up to this point, we had had no problem with pickpockets. I had been holding tightly to my purse for the last five days, so I let down my guard.

I messed up.

Later, I would find that not only over $200 in Euros was missing from my purse, but Faith’s passport was also gone. But since we had not yet discovered this mess, we thoroughly enjoyed the day. Such as another sumptuous, outdoor meal in the shadow of the majestic tower of Pisa and climbing the stairs to the very top of it.

As we were leaving, I noticed an older South Korean couple. The man was struggling to help the woman balance on top of a rounded baluster so he could take her picture “holding up the tower.”

Thus, this aggressive American (me) tromped over, took hold of the woman so she wouldn’t fall, and instructed the man to take the picture. While he snapped the photos, I felt a hand on my back and turned to see a line of about 15 South Koreans, in single file, behind me. Each one holding onto the person in front of them.

We all were holding up the tower together.

Three other photographers had joined the initial photographer in snapping this opportune moment.

Somewhere in South Korea, I am in a lot of vacation photos

the obligatory pic-holding up the leaning tower

When first entering this historic area, you see hundreds of people lined up for blocks, their hands held high to hold up the leaning tower. All with a willing photographer to catch the special moment.

Two Bumbling Novices Meet An Italian Cat

Faith and I continued on our way and spotted a nearby cat asleep in a yard. Being an animal lover, I called the kitty in English. However, he didn’t move a muscle.

Then, I called “Qui, Gata, Gata!” in the faltering Italian I had learned. The cat’s head perked up, looked in our direction, and he came bounding over for some pets.

Therefore, we learned that Italian cats speak Italian.

Time To Go, And Dang It, I Messed Up Again!

Regrettably, it was already time to leave Italy. Somehow, we were up at 5:30 AM for the three-hour drive back to Rome. We wanted to be at the US Embassy by 8:30 AM in a desperate attempt to make our 11:35 AM flight.

It only took an hour and a half to get Faith a temporary passport. In a vain attempt to make our flight, we sped to the airport. When we got there, they had just closed the call for our flight, and we were forced to stay another day.

Forced to stay an extra day in Italy? How awful!

Seriously, we were so tired, all we wanted to do was sleep. We had gotten up every morning at dawn and left, only to return around 11 PM every night. Which was necessary, because how did we know if we would ever make it back again? Thus, we had to see everything we could!

I found a little place in the airport where business travelers often spend the night and booked a room. The plan was to get a shower and then see a bit of Rome.

Which didn’t happen.

After our showers, we fell into our beds and slept for 16 hours. Yes, we did!

So, we made it back home but didn’t get to see any of Rome. Therefore, I guess a return trip is required.

Thus, I messed up again! Or did I?

After arriving back home, Faith and I realized neither of us experienced even a tiny bit of jetlag! All we had to do was sleep 16 hours before our overseas flight and swallow a few jetlag-prevention tablets, which I bought at Target.

What You Can Take Away From My Screw Ups

To be honest, the primary purpose of this post is to entertain and hopefully create a few smiles.

However, there is another purpose.

If I, a 56-year-old woman, can take my 19-year-old daughter on our first trip overseas, you can, too!

Sure, I was nervous and slightly terrified.

But my desire to go was stronger than my fear. And for that, I’m very thankful.

Even though I made a few gaffes, Faith and I both survived. But, would we do it again?

Yes, in a heartbeat.

We had the most magical time and fell in love with this beautiful country, its culture, and its people.

As a result, I didn’t really mess up at all!

Oh, yes, and then the speeding and parking tickets began arriving in the mail. 14 in all. Did I mention Italy has no need for shoulders on their roadways because they have traffic cameras everywhere?

Hiking in Cinque Terre


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  1. Talk about a whirlwind of adventures! This makes for a great story and you guys will never forget this trip. Thank you for sharing!

  2. Great, fun story. Sometimes vacations that start out with glitches are the best ones ! I loved Italy. Did not get to Tuscany – next on the list,

  3. Wow what an adventure! Sounds like you guys had a crazy but great time. I’m impressed you guys trained for the stairs! So smart and at least that Italian helped with the cat! This was a great memory and bonding time for you both. I’m sure your daughter will never forget such an amazing trip even with the few funny stories- but coming home to 14 tickets? geesh!

    1. Yes, it was the one unpleasant part of the experience. If you ever drive in Italy, mind the speeding laws and familiarize yourself on where you can and cannot go.

  4. What a delightful read. I can totally relate to not being able to find reverse on your rental car. Im beginning to learn to check all out before leaving the rental yard.

    Oh my on the speeding tickets!

    I do want to visit Italy!

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