Written for Harpers Bazaar
After a soul-searching southwestern road trip and an introspective solo “honeymoon”, it was time to head to my happy place: Italy. I’d always adored the warm southern country and dreamed of somehow, some day, calling it home. Maybe now, with nothing holding me back, would be the time?
Armed with an August free of obligation and an opportunity to visit a Tuscan vineyard, I seized the chance to spend my final weeks of freedom in the land of red wine and renaissance architecture. I agreed to every passing invitation from friends, ex-colleagues and media contacts and planned an Italian tour entirely hosted by locals with my Italian-speaking, can-drive-a-stick-shift, gets-along-with-everyone girlfriend, Jackie. With visions of blazing through the Italian countryside in a convertible Fiat, headscarves flapping in the wind, Jackie and I hopped on a nonstop flight from JFK to Rome.
Once on Italian soil, we rented a car (an Audi station wagon as they were tragically out of Fiats) and pointed our compass toward a remote destination off of the coast of Tuscany called Monte Argentario. We planned to stay with Rufus, a quirky British Earl I had known for a decade, who spends every summer in his bohemian seaside villa, 2.5 hours from Rome. As we approached the island peninsula, the landscape merged from rambling countryside to rocky mountains. Fluffy grasses flanked a single, narrow road that encompassed the mountain. We tried not to look down the cliffs at the water far below as Jackie navigated the enormous Audi around each hairpin turn, with toy-like vintage cars whipping by us with ease. Following Rufus’s directions that sounded more like a Shel Silverstein poem than a map, we passed through the pinkish town of Porto San Stefano, climbed the last bumpy hill to the thicket of olive trees and waited for another car to let us through the rickety wooden gate. Rufus, roguish gentleman in his fifties, welcomed us with sunscreen kisses alongside his Dutch, ex-supermodel (then) girlfriend and their two impossibly gorgeous, bronzed teenagers. For the next few days we spent our mornings on the rocky beaches, our afternoons barefoot at the single, seaside cafe and our evenings over relaxed dinners at the private homes of Rufus’s many friends. In the far-flung resort town frequented by the European jetset and Italian vacationers, we were an anomaly. Upon overhearing our American accents on the beach, one genuinely perplexed sunbather asked Jackie and I how we got there .
Comprised of Italian, French, and a few untraceable accents, this well dressed crew seemed to handle everything from dinner conversation to divorces with relaxed grace. Monte Argentario’s community of seasonal locals was so much more intimate than other European resort towns that I felt tempted to accept our new friend’s invitations to stay longer. On our last night, we feasted al-fresco in a sprawling, multi-level home set into to the mountain’s edge. Courses of risotto, local cheeses and tender veal cutlets were all hand-prepared by our host and we served ourselves, sitting casually around the patio. The full moon lit up the ocean and our little party, and as the wine flowed freely, an amusing battle over the music began. Soon we were up on our bare feet, dancing and twirling alone and together under the glow of the night sky. Eventually we collapsed breathless and scattered on picnic blankets and chairs, and I wandered off to the kitchen for a glass of water. There, I stumbled upon an unlikely couple stealing kisses and I backed out quickly, blushing. Two teenagers sauntered by, returning from their own party, and their parents greeted them warmly before sending them up to bed, unfazed by the late hour. Despite the perceived familiarity of the moment, I realized how little I actually knew about these people. This laid back luxury was intoxicating, but surely their regular life outside of August was much more...regular? If I made real moves toward a life in Italy, surely it wouldn’t be this glamorous… would it?
In the morning Jackie and I bid adieu to ocean views and headed inland toward Montalcino, home of Brunello di Montalcino. An American friend with ties to the food and wine industry had spent time in the tiny town as a wine distributor, and so set us up with her colleagues at Franci, a locanda, or bed and breakfast, with three fairytale rooms. Hosted by the husband and wife owners, we sipped from bottles of Brunello older than us, while listening to the bells of the medieval village below. Bellies full and a little tipsy, we stumbled toward the Fortezza for a tour followed by a more “official” wine tasting inside. Here we were greeted in the Fortezza’s Enoteca by Arnot, a jovial sommelier with a Cheshire grin bellowing, “I’ve been expecting you!” Seeing him behind the bar, huge balloon glasses and rows of bottles ready for sampling, I imagined this shiny, bald man to be the gatekeeper to heaven. If Arnot wasn’t friendly enough before, his enthusiasm multiplied when he found out that I’m half Belgian, just like him. Suddenly the pours became more generous, and in a mix of French, Italian and English, the three of us joked like old friends and soon it was clear that a case of wine (each) was an essential souvenir. A great investment for someone who doesn’t have an actual home–but then again, what better thank you gift for all of the friends housing me back in New York? After expressing my fantasy of living a real life in this magical Tuscan town, Arnot scoffed while proposing that “moving to Montalcino is simple… Just marry me!”
My boozy buzz subsided but the magic of Montalcino continued when Jackie and I accepted a dinner invitation at Cupano, one of the region’s most well respected vineyards. Here we met Ornella, a woman with style and wit that defied her aged years. Lionel, her equally sharp and subtly charming French husband, gave us a brief overview of their decades spent cultivating the perfect grape. He also explained their aversion to modern conveniences like electricity, noting that until fairly recently they’d lived almost completely off the grid. Despite eventually acquiescing to the usefulness of creature comforts, their enormous rambling farmhouse remained rustic and simple. Our meal was of the same vein: eggplant caponata and cheese followed by grilled branzino topped with lemon and olive oil, roasted potatoes and wilted spinach. We savored each morsel from the dirt floored, vaulted brick patio while watching the sun set over the vineyard. Without music or distraction, the flavors of our food came alive as did the stories of these two complete strangers, as interested in our foreign lives as we were in theirs. Considering the success of Cupano, I mused on Lionel and Ornella’s choice to live such an uncomplicated life, willing it to someday be my own. It took every bit of self control (and Jackie’s nudging, she did still have to drive after all) to deny just one more glass of wine by the fire pit and a bed upstairs for the night.
Instead, at dawn I shelved my dreams of the simple life and headed north towards Castelfalfi. Here, an 800 year old Medici estate between Volterra and Florence was converted into a resort compound with villas and apartments, a golf course and two hotels. Upon arrival, we learned that we were just in time for Ferragosto, a huge Catholic Italian holiday of which I’d previously been ignorant. As Italians do, Ferragosto is celebrated with a feast. And so, on our first night in town, Jackie and I were invited to an elaborate buffet at one of Castelfalfi’s two restaurants, La Rocca, perched high atop the castle walls. Wandering up through the Borgo, or village, timeshare owners prepared for a festive night: the bustling sounds of aperitivo, the Italian happy hour, could be heard everywhere, and the impossibly clean streets were notably lacking many children or elders,reminding me of designer Brunello Cucinelli’s elegant compound just a few miles over in Solomeo. We arrived to the Michelin-starred feast just in time to fill our plates with every delicacy imaginable before watching the sun set over 2,700 acres of private countryside. As I glanced around at the other tables, mostly couples and yes, a few families of all ages, I wondered where they spent their real lives. From the sound of it, this holiday destination was a respite from countries outside of this one. I considered what it would be like to become neighbors with Stefano Ricci, vacationing regularly in one of the Castelfalfi apartments. But real life this was not, and so the search for a home continued.
After our Tuscan tour, Jackie and I bid arrivederci to our Audi in Florence and continued by train up to Lake Como; home to Max and Andreas, friends I had met only six months earlier in Costa Rica. Exhausted from the five-hour journey, we were thrilled to find Max, grinning and waving his long arms from his convertible Volkswagen Bug just outside of the train station. At 6’5”, I wondered if Max ever put up the hood or preferred to cruise around even in Como’s snowy winters with the top down out of necessity. Max had insisted we take his apartment during our stay, while he crashed around the corner at his parent’s more spacious home. For the first time in our “live-like-locals” adventure, Jackie and I were the closest to living like locals. Max’s comrades were as welcoming as he was, and in addition to boating us around the lake and dazzling us by embarking from the landmark Hotel d’Este, they also shared their favorite local haunts. We sampled everything… from the wineshop turned gastronomia, Castiglioni, to Osteria Del Gallo, a Como classic where friends had celebrated a recent wedding. At Caffe dei Viaggiatori, Max introduced me to a local specialty that sounded terrifying but quickly became my obsession: a delicate slice of chilled veal slathered in velvety tuna paste called vitello tonnato. As we wandered the idyllic streets lined with gelaterias and posh shops, I imagined the possibilities of a life here. I mulled over the idea of picking up my styling business from a city like Como, and ran it by a fellow American expat at dinner. The American, a successful musician, and his British wife were just a few years older than I and they hadn’t looked back since transplanting to Como two years before. Now, they were building a bed and breakfast that would cater to travelers seeking a stylish yet unpretentious travel experience, and encouraged my idea to move. Providing an asterisk to the husband’s conviction, the wife warned of Como’s sleepy winters and resort dependent business. I considered the realities of a city built on seasonal tourism and decided that Como, while very liveable, just wouldn’t be for me. And so once again, despite invitations to stay, we said our farewells and promised to keep in touch.
Finally, a lengthy train ride took us back down to Rome, where Jackie and I had just 24 hours to spend before returning to NYC. Over the past weeks I had daydreamed dozens of potential lifestyles from the more realistic (styling in Como) to the farfetched (running a bed and breakfast in Tuscany). I had discovered on my American road trip a few months earlier that community and work were the two non-negotiables required from my next home. While most of the places we’d visited had friends that could help build my community, I worried about leaving those dearest to me back in the US. Plus, being self-employed, the thought of acquiring a work visa without a company to sponsor me seemed daunting. But there was no time for moping, Jackie and I still had one precious day in the country we shared as a favorite, in a city we both knew well. Without the pressures of sight-seeing or staying with friends, Jackie and I reveled in a slow-moving morning at the classic Hassler hotel where we’d splurged for our last night. We avoided the afternoon heat—and the tourists—by ducking into tiny shops and befriending trattoria owners over unrushed meals. We did, however, have one more acquaintance to meet, one I hardly knew at all. I had met Luca* on my birthday months earlier, and we shared a whirlwind romance during a business trip that brought him from Los Angeles to New York. Besides some pretty creative emoji banter, we hadn’t really spoken since. But if ever there was a time to be bold, it’s when in Rome… So, sounding much like a Carnival announcer, I texted “Luca! For one night and one night only, I’ll be in Rome next week. Wanna give a girl a tour?” Within moments of hitting send, I got a reply; “Ciao Bella! I’m in Sardinia, but that’s my last day in Rome too, let’s do it.” My stomach fluttered with excitement but also fear. What if he wasn’t as cute as I remembered? Or our conversation was super awkward? But we agreed to meet for gelato and a nightcap along with Jackie and his friend, Francesco*. Turns out, Luca was far cuter AND more clever than I’d remembered and I immediately regretted not planning to meet sooner. To Jackie’s delight, Francesco’s clear green eyes and accent were captivating enough to distract her while Luca and I giggled and swapped spoons, trading pistaccio for Nutella.
Long after our gelato had run out but not wanting the night to do the same, the four of us decided to take a midnight stroll through the city. Hanging back from the others, Luca reached shyly for my hand as we left the piazza, and by the time we passed the colosseum we were arm in arm. Silent and lit from within, the massive structure stood even more majestic than under the scorching light of day. Without the crowds, the ancient city was ours. Soon we came upon the glowing Trevi fountain, unusually quiet without the throngs of tourists. I shut my eyes tight, making a wish as I tossed a Euro over my shoulder. Luca and I shared our first (sober) kiss around that time, and the rest was a blur of canoodling until we climbed the Spanish Steps bringing us back to our hotel. From the window of a passing cab we heard a jovial voice shout “get a room, you beautiful lovers!” as we stood kissing and talking in the street like teenagers. “I’ll be in New York again soon, and I’ll take you on a date” Luca promised. I told him I’d be in Los Angeles sooner, having already planned it as my next destination and he offered to show me Palm Springs some day. I thought how unlikely either of these scenarios were, but then again, so was this one.
Before we could meet or disappear from one another’s lives again, we ran into each other at Fiumicino airport the next morning. Somehow we hadn’t realized our flights were at the exact same time (9:55 am) from the same terminal (5), going to opposite coasts (JFK and LAX). I thanked my lucky stars that I’d taken the time to put in my contact lenses that morning and we shared one last lingering kiss in front of Duty Free before boarding. I walked onto the plane stifling a grin and watched Roman Holiday before falling asleep. I may not have sorted out my dream life in Italy, but at least for now, I was living a dream.