Ah, family vacations, those magical stretches of time where memories are made, bonds are strengthened… and everything that could possibly go wrong somehow does. Our trip to Italy was filled with sunshine, gelato, ancient ruins, stunning coastlines, and a spectacular series of logistical misfires that no amount of planning could have prevented. From lost luggage to rogue hills, unexpected air-conditioning hierarchies to fine dining hijinks, it was the kind of trip where “We’ll laugh about this later” became our unofficial motto. And now, dear reader, we invite you to laugh with us, as we present some of the best (worst?) travel fails from our epic Italian summer adventure.
The One Where Ally Called the Airline 1,000 Times 📞🧳
Our Italian summer escapade started with high hopes and tightly packed bags. Jon, ever the optimist, crammed his essentials into a small carry-on to avoid the hassle of checked luggage. The plan? Keep it with him the whole way. The reality? A flight attendant at the gate gave it one look and tagged it for the hold.
No big deal, until their layover in Lisbon went sideways. A delayed flight meant Jon, Ally and family missed their connection to Rome. As for Jon’s suitcase? Who knows. It certainly didn’t make it to Lisbon. Or Rome.
With many hours to kill, Ally insisted Jon buy a change of clothes. He skipped the changing room (rookie mistake) and grabbed items by size. Cue the moment he realized European sizes are not the same as U.S. ones. The shorts were indecently short. The underpants could qualify as compression wear. The shirts were… let’s say form-fitting.
After a long day of Lisbon limbo and more flight delays, they finally arrived in Rome at 1am, sweaty, tired, and still bag-less. That’s when Ally went full detective mode. Every spare moment, morning, night, mid-gelato, she was on hold or arguing with a new rep from the airline. That’s if anyone answered the call in the first place. The rest of us began to time her calls. By the last day, huddled in a Venetian restaurant hiding from the rain, she checked her call log and gasped:
1,004 calls.
One. Thousand. And. Four.
Three days after we got home, the suitcase reappeared on their Virginia doorstep: relaxed and well-traveled. Jon tossed the entire European wardrobe into the donation pile. And Ally? She still twitches every time she hears hold music.
The One Where Mandy Walked Us Up a Hill 🥵⛰️
After a long, joy-filled day in Rome capped by some excellent Cacio e Pepe at the Instagram-famous Tonarello, we said goodbye to our friends and prepared for the walk back to our Vatican-area apartment. The riverfront stroll had been lovely on the way in, but Mandy had other ideas.
In a heat-hazed moment of optimism, she suggested a shortcut. “Just up this little hill and we’ll loop back to the river,” she said cheerfully.
Spoiler: there was nothing little about that hill.
What followed was a sweaty, uphill slog past garbage trucks, a random open-air theatre, and several unimpressed locals. Fifteen minutes in, we finally descended… only to find ourselves right back where we started.
The kicker? Adam suddenly stopped in his tracks, looked around with dawning horror, and announced to the group:
“You buffoons! We’ve been here before.”
Mandy is now banned from navigating while talking. Or walking. Or really, navigating at all.
The One Where the Kids Got the Air Conditioning 🧊🛏️
Italy in July: gorgeous, yes. Comfortable? Absolutely not. During our stay in Vernazza, we booked three charming rooms at a harborside hotel. The twist? The rooms weren’t actually by the harbor, they were up, up, and up some more.
Dragging our bags up steep stone stairs in the blazing sun was a bonding experience we’ll never forget (though we’ve tried). We divvied up the rooms without checking them: adults claimed the first two, and the three older teens took the third room at the top.
We returned later that night from a perfect day on the water, ready to collapse. Except… it didn’t cool down. At all. We tossed, we sweated, we cursed the fans. The next morning, the parents stumbled to breakfast looking like survivors of a sauna session.
The teens, however? Bright-eyed. Rested. Suspiciously smug.
Turns out their room had glorious, blissful, hotel-grade air conditioning. And they hadn’t thought to mention it. That was the last time we assigned rooms without a full inspection.
The One Where the Kids Discovered Fine Dining 🍽️💸
Another gem from Vernazza, apparently the epicenter of our misadventures.
One evening, the group split: adults to a relaxed harbor-side dinner, teens to their own night out, armed with a credit card and one single rule of “send proof-of-life photos.”
We adults took the easy route, choosing a breezy table by the water to watch the sunset in peace. Meanwhile, the teens hiked to a hilltop restaurant someone had recommended earlier, one known for sunset views, romantic vibes, and, as it turns out, phenomenal food.
We sipped wine. They sent photos. Gorgeous, glowing, golden-hour photos of gourmet dishes and million-dollar views. Their smiles? Radiant. Our wallets? Suddenly lighter.
Was it worth it? For them, yes. For us? Let’s just say we now include the phrase “no fine dining unless we’re invited” in every family meeting.
As much as we love to plan (and over-plan) our trips, it turns out that the most unforgettable moments are often the ones that go hilariously sideways. While Italy delivered on every postcard-perfect promise: jaw-dropping views, soul-satisfying meals, and that unbeatable golden-hour light, it was the fails that turned this trip from great to legendary. We may have gotten lost, overheated, overcharged, and utterly outmaneuvered by our own kids, but we also gained a collection of stories that will be retold at family gatherings for years to come.
So here’s to missed connections, accidental hill hikes, and teens in five-star dining rooms, because sometimes the best adventures are the ones you never meant to have.
Ciao for now… and on to the next challenge!
Go Together Life 
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