As featured on Smart Move Italy.com – Bedtime Stories
Once upon a time in a city that never slept—because who needs sleep when you have a 24-hour taco stand? —Where the buildings scratched the clouds like an overzealous cat lived a ridiculously good-looking and successful couple still searching for La dolce vita. They’d been at it for 21 wild, wacky, and utterly exhausting years, pretending to live the high life in this occasionally heartless concrete jungle, all while secretly wondering if “high life” meant a never-ending supply of espresso and overpriced avocado toast.
Then, on a day that was destined to be legendary, the sea decided it was time for a surprise visit and gave the land a big, soggy smooch, sending both of them crashing back to reality with a comedic thud. Enter Hurricane Sandy, the dramatic diva who waltzed into NYC in October 2012, turning the city into a watery disco and prompting everyone to cha-cha away from their usual routines—some even did a complete life makeover!
For a whopping 8 days, 50% of this bustling hive of 11 million souls experienced a blackout that made us all feel like we were living in a low-budget dystopian movie—no power, no work, just people wandering around like confused zombies searching for Wi-Fi!
With no restaurants, no entertainment, and no distractions, people suddenly found time to daydream—or, let’s be honest, freak out a bit. In this unexpected timeout, Raymond and Leonardo took a long, hard look at their lives and realized they were both on the same quirky wavelength: they yearned to trade their hectic city lives for a sun-soaked return to their Mediterranean roots, chasing that elusive dolce vita—basically, living like a couple of pasta-loving beach bums!
When the power finally flickered back to life and our dynamic duo returned to their desks, they started pondering their future as if they’d suddenly won the lottery—except without the money, and wearing their “I’m a responsible adult” hats. They figured it might take a miracle, a magic wand, or just lots of caffeine to shake things up and transform their lives!
Then in 2014, as the American people prepared for another presidential election campaign, there was a sense of excitement about the possibilities that lay ahead, even amidst the surprising emergence of a bombastic reality TV star as a contender. This sparked renewed energy and enthusiasm, prompting many to start thinking about positive changes and new opportunities for their future.
They embarked on a heroic quest to find their next big trip, launching a full-scale expedition into the depths of the ‘Goggle search’ rabbit hole, armed with nothing but their wits and a questionable amount of coffee. After an epic saga filled with animated debates over pancakes, sandwiches, and very fancy dinners (because who doesn’t love cramming their faces while plotting?), they triumphantly declared, “Bella Italia, here we come!” as if they had just discovered treasure instead of just another pizza place.
Now that the big decision was out of the way, it was time to get down to the nitty-gritty details. Our couple had watched so many relocation shows, like House Hunters International and Escape to the Continent, that they’d practically earned PhDs in house hunting. Armed with pen, paper, and a cup of dubious coffee, they embarked on the epic quest of brainstorming everything they wanted in their dream home. What would this new life smell like—freshly baked cookies or something suspiciously similar to gym socks? What about the taste—gourmet meals or takeout sushi that always mysteriously comes with extra soy sauce? And let’s not even get started on how new life would look—like a Pinterest board exploded in a house or a toddler’s art project gone rogue!
Words like “farmhouse,” “traditional,” “rustic,” and “renovated” spark excitement, as they bring to mind wonderful outdoor spaces, stunning views, and the charm of a city, town, or peaceful field just waiting to be explored.
“We must have at least three bedrooms,” one said
“Yes,“ the other concurred, “and two bathrooms.”
“A garden or terrace or perhaps some land? Raymond queried
“Maybe an olive grove?” Leonardo added
As they bickered over their wish list like two toddlers fighting for the last cookie in a cookie jar, they finally settled on a budget that resembled a toddler on roller skates—wobbly and highly questionable! They unfurled a map of the ‘boot-shaped’ country as if it were a secret treasure map leading to endless riches (or at least, endless gelato). Their wild escapade kicked off, sweeping through the land from the frosty north, where penguins donned their best winter coats in a fashion show, to the sunny south, expertly dodging sunbathers and ice cream trucks like pros. They navigated from towering mountains—where a yodeling llama might just be their new guide—to the salty sea, all in a wonderfully ridiculous mission to find the Holy Grail of gelato!
“Definitely close to amenities, possibly near the French border. Imagine going to France for lunch!” exclaimed Raymond.
For the next few months, the couple dived into house hunting like it was an Olympic sport, marking potential towns and homes with the enthusiasm of kids on a treasure hunt. Once they finally pieced together a plan that resembled a mildly coherent map rather than a spaghetti spill, Raymond triumphantly booked a flight, crammed their suitcase with dreams (and maybe some snacks), stuffed his pockets full of hope, and took off across the pond like an overly optimistic pelican.
In July 2015 Raymond landed in Nice, jumped into a rental car, and set off across the border into Italy.
He traipsed along the Ligurian Sea’s coastline from Imperia to Genoa, then hopped over to La Spezia, swung by the Cinque Terre, and finally ended up in the Tuscan coastal town of Livorno. While the views were picturesque and worthy of a travel brochure, let’s be real—navigating those rocky cliffs felt more like a workout than a vacation! It was all very dramatic and romantic, like a scene from a movie, but living there? Unless he had a mountain goat for a roommate, he figured maybe a flat in the suburbs sounded more practical.
After what felt like a never-ending Olympic marathon trapped in cars, stumbling through houses, and ricocheting between towns and villages, Raymond landed himself in a downright hilarious case of Goldilocks Syndrome—everything was either as huge as a royal castle, as tiny as a dollhouse, had views so bizarre they made him reconsider his life choices; hills steep enough to confuse even mountain goats, prices that would make a piggy bank faint, or just looked like it was auditioning for a reality show titled “Extreme Makeover: House Edition—What Were They Thinking? ”
Add to this the delightful chaos of Italy’s breathtaking views, scrumptious pasta, and a steady flow of Aperol spritzes, and his brain was doing somersaults, rendering any reasonable decision as elusive as a pizza slice at a diet convention.
Thankfully, their inaugural adventure in Bella Italia wasn’t a total flop; they walked away with a crystal-clear list of definitely-not things! Who knew figuring out what you don’t want was just as crucial as knowing what tickles your fancy? It’s like ordering a pizza and realizing you really can’t stand pineapple on it—who says you can’t learn anything on vacation?
Raymond made a triumphant return to NYC, and they leaped straight into the wild and wacky world of ‘Google Search’ like kids in a candy store, armed with nothing but a stash of snacks and a foolproof plan to unravel the age-old mystery of why cats can’t resist the urge to launch everything off tables!
In February 2016, he made his grand return to Italy, this time setting up camp in the illustrious Tuscan town of Cortona. Little did he know he’d be sharing this picturesque paradise with a Russian real estate agent straight out of a fashion magazine—glamorous, charming, and a little bit off her rocker. Behind the wheel of her pint-sized smart car, she transformed from delightful diva to a turbo-charged terror, zooming through the streets as if she were auditioning for a role in a Formula 1 movie, complete with dramatic tire screeches and reckless abandon.
They joyfully zoomed through the enchanting Val d’Orcia, eagerly visiting many of the renowned medieval towns like Lucca, San Gimignano, Pienza, Radicofani, and Cetona, where his guide skillfully maneuvered her car into petite spaces and whisked him in and out of charming properties with the grace of a whirling dervish in stylish 3-inch heels.
And they also crossed the mountains into La Marche and scoured the coastline of the Adriatic Sea.
Over those six days, she somehow managed to drag him through over 40 properties that ranged from a questionable pile of bricks in a field at the bottom of a ravine to grand estates that were so outrageously out of their budget it could make a comedian weep—at this point, the laughter was less about joy and more like a frantic coping mechanism!
With just one day to go and his brain still doing somersaults, he decided to make a break for it, expertly dodging her devilish grip as if it were a game of Twister gone wrong, and with a grin, he politely turned down her offer to tour another 10 ‘Zimply divine’ houses that day, because let’s be honest, even the best housewarming gift couldn’t make that kind of torture worth it!
Instead, after a lazy breakfast he gathered his wits about him and decided to just get in the car and see where he ended up.
He cruised south from Cortona, zipping past Lago Trasimeno like a contestant on a reality show about scenic drives, navigating those twisting country roads into Umbria. A pale sun was shining so bright in the cloudless blue sky that it practically needed sunglasses, and on that picture-perfect winter morning, it seemed like the universe was throwing a giant cosmic party just for him, with stars aligning and the gods grinning down like they just heard the best dad joke ever.
“You’ll never believe it, but I’ve found the perfect town for us!” he declared, catching Leonardo off guard with a late-night wake-up call from NYC. “It’s called Citta della Pieve.” He went on, taking a grand sip of what he claimed was the best cappuccino since the dawn of time, “I mean, if they serve this kind of coffee, imagine how the gelato will blow our minds!”
CITTA DELLA PIEVE
Citta della Pieve was a medieval hamlet that casually perched on a hill, as if it were a royal guard keeping watch over the unfolding drama between Umbria and Tuscany. It wasn’t your typical snooze-inducing medieval hilltop town—oh no, this place was about as crowded as a farmer’s market on a rainy day, making it the perfect getaway from the infamous tourist stampede!
Citta della Pieve had a tangible life force, energy, and a pulse that transcended just being pretty to look at or a magnet for tourists.
It was a genuine Italian town, alive and kicking, radiating a warmth that made you feel like you were being hugged by a giant lasagna. The charming red brick buildings looked like they were showing off their smiles, while the narrow winding streets were bustling with locals of all ages, trying hard not to trip over each other as they argued over the best pizza toppings. Meanwhile, the cafés were buzzing with groups deep in conversation—not about world peace, but rather the great debate of whether to have another espresso or if that’s just a sign of weakness.
It had been less than a year since they hatched the brilliant plan to move to Italy, and I can hear the collective gasps—“They must be bonkers to base such a monumental life decision on a whim!” But hey, when you know, you know, right? Sometimes you just need to channel your inner pirate, throw caution to the wind, and trust your gut, even if it’s telling you to swim with the pasta!
As Raymond lounged in the winter sunshine, cradling his cappuccino like a prized trophy while eyeing the waiter chatting to guests and passersby, he thought – Well, this is it! You’ve hit the jackpot of chill vibes. Now, what’s the game plan? Maybe audition for a reality show about hip lounging?
The day Raymond swaggered back to NYC, they dove headfirst into the chaotic world of house hunting in the enchanted land of Citta della Pieve. Just as they were about to unleash their epic search criteria—probably involving unicorns and a moat—the very first house that flashed across the screen was none other than their soon-to-be farmhouse on the hill, as if the universe decided to skip all the hassle and say, “Here you go, future farmers of nonsense! ”
Their hearts skipped a beat; this house was so perfect it could’ve auditioned for a reality show—between the size, the location, the dreamy garden, and a budget that didn’t require a second mortgage, it was practically begging them to move in and throw a party!
Was it too good to be true?
They immediately fired off an email to the agent, practically holding their breath in anticipation—like they were waiting for a text back from their crush. Days turned into an eternity, a week passed, and still no reply. So, they thought maybe they should try again, you know, in case the agent was busy cuddling their cat or something. Meanwhile, they continued their house hunt, but somehow, each time they found themselves creeping back to that charming house on the hill—it was clearly playing hard to get.
Finally, they got a response—though, as it usually goes, it felt like waiting for a snail to finish a marathon! It turns out international agencies, in their infinite wisdom, love to showcase properties on behalf of smaller agents by plopping them onto their own sites, which sounds great until you realize it means the vendor’s hopes are now stuck in the slow lane, leading to responses arriving at a delightfully leisurely pace!
Raymond shot an email to the local agent, stating that he had just returned from a wild property hunt in Italy—yes, he actually lost a shoe in a vineyard—but before he could consider a second round of house hunting, he absolutely needed a video tour of the entire house, inside and out. After all, who doesn’t want to see the kitchen where the fridge might hold more secrets than the local gossip?
A few days later they got the video……………
The video was a real treat—Sure, the house looked like it hadn’t seen a visitor since the dinosaurs roamed, and yes, it might just qualify for a reality show about the worst home renovations, but hey, the structure was stronger than your Aunt Edna’s fruitcake! The rooms had enough potential to launch their own Instagram influencer careers, and those views? Absolutely chef’s kiss! Bursting with excitement, they called the agent to declare that Raymond was making a whirlwind trip to Italy just for this house. Naturally, they needed a little reassurance that it wasn’t some kind of online mirage—because let’s be honest, some properties linger online longer than stale bread, and those listings could use a serious makeover themselves!
Assurances were given quicker than you can say “plane ticket,” so Raymond booked a flight, touched down on a Saturday morning in late February, played house tour guide, and promptly made an offer—because who doesn’t want to own a farmhouse on a hill, right? By Monday, the owner was more than happy to say yes, and in just 10 days, they were the delighted (and slightly bewildered) new owners of their very own rustic slice of heaven!
Now all they had to do was master the fine art of closing and selling a business, pack up their apartment and storage unit—good luck squeezing that inflatable dinosaur in there—and organize a game of Tetris with their worldly goods to get them across an ocean. Oh, and let’s not forget the emotional rollercoaster of saying goodbye to their wonderful friends, who wouldn’t stop asking why they were abandoning ship. Finally, they’d board a one-way flight to Italy, armed with nothing but hope, cheese dreams, and a questionable amount of luggage!
They drove along the white gravel road, their hearts fluttering like startled pigeons as their 200-year-old “new” home came into view, a towering structure all shuttered up like a gigantic hibernating bear, ready to waken and demand breakfast after years of relentless beauty sleep.
As they approached, they found that Mother Nature had pulled off her best springtime magic trick, transforming what had once been a posh front garden into a wild jungle fit for a family of serious garden gnomes, with tree shoots and weeds shooting up almost 6 feet high—clearly, even the garden forgot about February’s pruning party!
They wrestled their way through the jungle of overgrown plants, fished out the door key from beneath a suspiciously heavy pot, and with a theatrical flair, clapped their hands like a couple of overly enthusiastic seals before flinging the door open and shouting, hoping to spook away any uninvited party crashers who might have taken up residence!
They dashed from room to room, bounding up the three floors like caffeinated bunnies, flinging open the shutters as if they were auditioning for a home improvement show, letting the sunlight and wind chaotically waltz through the empty house. As they descended back down the stairs, they couldn’t help but notice that the old terracotta floors resembled a rollercoaster more than a flat surface; they were practically on a water-themed adventure, the walls were shedding paint like a bad case of dandruff, the color palette screamed “vintage thrift store,” and the fitted kitchen looked like it had time-traveled from the days when disco was king!
By the time they reappeared in the jungle they once called a garden, their excitement had transformed into a fierce determination—because apparently, starting a new dream life also required a degree in horticulture and a whole lot of elbow grease. Time to roll up those sleeves and dive headfirst into the chaos of starting over, armed only with optimism and a questionable number of garden gnomes!
The building restoration kicked off indoors: Imagine the undulating stone floors donning their new pink terracotta outfits, looking fabulous! The walls got a fresh plaster job, while the old kitchen cabinets, well, they were kicked to the curb for some dazzling oak units and glitzy Carrera marble countertops. The walls got a makeover too, along with all the light fittings that got the boot. A local woodworker, probably armed with a coffee and a toolkit, was recruited to whip up some fitted storage throughout the house—because, let’s face it, who doesn’t need more places to hide the clutter? All this action was happening while they were twiddling their thumbs, waiting for the ‘Permesso’ (permission) to jazz up the outside of the house by fixing the mortar—which turned into an epic saga. For three weeks, starting at the crack of dawn, it was like a thousand woodpeckers were having a rave on the house with their relentless knock, knock, knocking. Spoiler alert: it was just the workmen, armed with their little trowels and hammers, playing archaeologists as they disentangled the concrete hugging those ancient stone walls!
Within six months, most of the work was completed, and despite feeling like they’d run a marathon in concrete shoes, they were surprisingly happy and chuffed with what they had managed to achieve using their charmingly limited Italian. They figured it was a magical blend of flailing arms, exaggerated smiles, a determined expression like they were in a cheesy rom-com, and the miraculous gadget known as Google Translate that got them through it all. Honestly, their tradesmen were so forgiving that it felt like they were handing out passes for ‘Terrible Italian Skills 101’; in fact, everyone in the town seemed to take delight in their baffling yet endearing attempts at speaking the language. We soon learned that the locals found it downright entertaining that we were so invested in their community, trying our best despite sounding like confused parrots, and after all the obstacles and hurdles we had to hop over, we just kept on smiling!
All the while, the bureaucratic dragon loomed on the horizon, guarding the shiny treasure that was Italian Residency. Our intrepid couple heard tales of woe from fellow expats who had struggled with this multi-headed beast of red tape. They figured, why not party like the Italians? So they gleefully decided to tackle everything at a leisurely pace—slowly, without breaking a sweat or screaming in frustration. This laid-back approach surprisingly worked like a charm. Whether it was ordering a plate of pasta or charming the Carabinieri at a roadside stop, their golden rule was simple: lead with a disarming smile, and hope for the best! This philosophy helped them wade through the murky waters of bureaucracy with a semblance of sanity. But as they set off to claim their residency jewel, they quickly learned that not all communes (town halls) or Questura offices were cut from the same bureaucratic cloth. Città della Pieve’s commune was like a friendly Italian grandmother, all hugs and warm cookies, while Raymond, being a British citizen, snagged his residency with the ease of spreading butter on warm bread since the UK hadn’t yet been ousted from the EU. Poor Leonardo, though, had a different saga; as an Australian, he felt like he was wrestling a three-headed dragon. His quest involved three years of tangled misinformation, more consulate trips than he could count, a truckload of translated documents, and an ongoing relationship with the Perugia Questura. In the end, just when he was about to throw in the towel, it turned out the magical answer was right there: if they got married in Italy, Leonardo would get his golden ticket. Who knew love was the ultimate bureaucratic cheat code?
So there they were, tying the knot in the commune—right in the middle of a power outage on a brisk December morning in 2018, with two bewildered locals looking on as if they’d just stumbled into a rom-com. And voila! A few months later, Leonardo finally got his Permesso, and just like that, the bureaucratic dragon was sent to take a nap, hopefully with a cozy blanket and some hot cocoa!
Once they had sent the dragon packing and given a new lease on life to the giant now whimsically dubbed “La Torre,” they were gleefully surprised to find that packing their bags for a new country was the easy part. Living there, however, was like tiptoeing through a minefield of hilariously awkward ‘translation’ faux pas and cultural hiccups. Imagine them stumbling over their own tongues while attempting to order a coffee and somehow ending up requesting a pet llama instead! These quirky blunders catalyzed a whirlwind of cringe-worthy moments and delightful surprises as they waded through the dense jungle of social cues and etiquette, all while proudly flaunting their shiny badge of being the “Straniero” (that’s just a fancy way of saying “the hilariously confused foreigner”) in town.
Everyone wanted to know their life story and what they planned on doing next.
Was it worth it? Was it the right decision? Was it what they expected?
The simple answer is yes, yes, yes.
But there is one very important ingredient in this story that Raymond believed was the true key to their success—charity! You see, he operates under the principle that whatever you’ve got—whether it’s time, experience, or resources, no matter how pitifully small—should be shared like it’s a free donut at the office. After all, sharing is caring, and who doesn’t love a little sprinkle of generosity on their day?
So almost from day one, he was on a quest to find a project they could physically throw themselves into, thinking it would magically connect them with the local Italian community and attract other charitable oddballs. And lo and behold, just weeks after touching down, they stumbled upon the perfect match—who knew charity could be as easy as finding the best gelato shop in town?
The Ceramic Lab Terrarte, nestled in the bustling Centro Storico, was like Hogwarts for special needs kids and adults—only instead of wands, they wielded paintbrushes and clay! It was all powered by volunteers who probably mistook the place for a pottery-themed reality show. Leonardo’s obsession with art and Raymond’s flair for community service had a delightful collision that created a legendary spot where creativity flourished—and so did the occasional playful pottery mishap!
It appeared that before they could say, “Oops, we need a handyman,” the restoration works were wrapped up, and their house transformed into a scene straight out of a cheesy sitcom, complete with a soundtrack of music and endless laughter. Folks from all corners of the globe showed up like they’d just won the lottery, ready to bask in their good fortune and indulge in a dolce vita that probably included more gelato than is medically advisable!
To celebrate their first anniversary, they decided to throw a massive shindig for their new pals, who they’d practically unwrapped like gifts on a hot summer night. As dusk set in, over a hundred guests strutted up the gravel driveway to La Torre, looking like a rainbow had exploded on them, humming Italian tunes that could charm the birds from the trees. Arms overloaded with baskets stuffed to the brim with the finest local produce—because who doesn’t need a hefty dose of vegetables? Meanwhile, music was blasting, and dashing waiters were doing their best impressions of superheroes while serving mouthwatering food and wine—pure bliss wrapped in a napkin!
THE GARDEN PARTY
During that first year, fueled by the wonderful guidance of the many friends they had made, they joyfully discovered a vibrant tapestry of food festivals, hidden art treasures, theater, vineyards, music festivals, and delightful spa towns, all right on their own front doorstep, waiting for them to explore.
Their fearless nature had launched them on a globe-trotting escapade in search of la dolce vita, only to discover it in Umbria—the green heart of Italy! Who knew paradise was just a pasta dish away? This charming place is so magical and beautiful that even the locals sprinkle kindness and compassion like confetti, especially during those tricky times when you realize your favorite wine ran out!
These days, you’ll find Leonardo at his antique writing desk on the top floor, gazing out at the breathtaking rolling landscape, probably pretending to be a tortured artist while composing prose. Meanwhile, Raymond is downstairs, either fussing over their garden like it’s a prize-winning potted plant or getting lost in art projects that even Picasso would raise an eyebrow at. And as the world speeds up its unlocking, they’ll ditch the homebound activities in favor of indulging in the delightful chaos of their charming town—or, who knows, they might just hop over to ‘Bella Italia’ to find out if the pasta tastes as good as the scenery!
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