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Guide to Renting a Villa in Sicily, Italy

Sicily,Italy,dinner guests,outdoors,eat,La Favorita,villa for hire,17th century

Photo: Andrea Wyner

“Enigmatic,” “ornery,” “inscrutable”: on the rare occasions that western Sicily comes up in conversation—let alone in travel guidebooks—it’s usually prefixed by one or more of those words. This, people tell you, is a region so insular that even Italians are flummoxed by the place. Its dialect, customs, and cuisine (couscous; spleen sandwiches) are a world apart from the mainland, and even from the island’s more touristed east coast. “If Sicily is another country, the west coast is another planet,” said an acquaintance in Rome. He did not seem to consider it a particularly friendly planet.

Despite or because of all this, when my wife and I decided to rent a villa in Italy in the company of five close friends, it was western Sicily that drew us all in. The sun-bleached coastline; the shadowy, souklike markets; the ancient temple ruins at Selinunte; the salt pans at Mozia; the cultural affinity with North Africa (hence the couscous): to us the west coast sounded mesmerizing, and its apart-ness from the Italy we knew was central to its allure. We took the region’s impenetrability as a challenge—a game in which a rented villa would be a distinct advantage. Under the cover of our borrowed house, we could embed among the natives: shopping for couscous at the market, sipping Aperol Spritzes with the neighbors. We would live like locals, just as all those villa-rental brochures promise, and unlock western Sicily from the inside out.

First, though, we’d have to find the villa. On the continuum of daunting travel experiences—Mexican cliff diving, flying Aeroflot, carpet shopping in Marrakesh—few spur as much anxiety as “renting large house in unfamiliar land.” You could liken it to a blind date, except this date lasts an entire week, can cost untold thousands of dollars, and levies a hefty penalty if you try to skip out early. Of course, with great anxiety comes great reward. Anyone who’s successfully navigated the vagaries of villa renting will agree that it was worth the time, stress, and money invested—and that the experience was more meaningful and memorable than any stay at an equivalently priced hotel could be. That certainly was our takeaway, after that strange and unforgettable week was over. Though we encountered plenty of frustrations, all seven of us look back on it as one of our favorite trips ever. Could we have done it better? Absolutely. Would we have changed a thing? Honestly, no. But we learned some essential lessons for next time.

Know what you want—and what’s beyond your reach.

Once our group had settled on our maximum price ($7,000 for seven adults and a child, for seven nights), we made a list of must-haves (four bedrooms; large kitchen for communal cooking; strong sense of place) and would-loves (ocean view; pool; housekeeping service). Those were just the basics—our actual list was a lot longer. The fantasy was to find a characterful old house near a charming seaside town, where we could sleep unbothered by car horns but still walk or drive to a local market, a good trattoria, and our soon-to-be favorite café.

Our list, it turns out, was overly hopeful. As several agents explained, “character” and “sea views” are a rare combination in Sicily, where the older, statelier houses tend to be located inland (on the former feudal estates their owners once managed). Since modern-day visitors prefer to be near the water, much of Sicily’s coastline is dominated by smoked-glass condos and 1970’s resort strips. So finding that charming old Stealing Beauty-esque villa—but one set by the sea—was not necessarily in the cards. We resolved to compromise: we’d trade a waterfront setting for a house with real personality.

Choose an agency with strong local connections.

Plenty of villa companies represent properties across the globe, and some do a very fine job. The key is finding an agency with people on the ground who can inspect properties and learn the terrain firsthand.

After browsing scores of listings from dozens of villa-rental sites, we got in touch with Think Sicily, a well-rated, decade-old agency representing 93 properties around the island. Though the company’s booking office is in London, its founding directors—Huw Beaugié, a British expat, and his Palermo-born wife, Rossella—live and work in Sicily.

We placed a call to Max Lane, Think Sicily’s local consigliere for the west coast, and relayed our wish list. We also sent him links to villas from other agencies that looked promising. Max came back with three properties that roughly fit our needs, all of them exclusive to Think Sicily. The standout: a seven-bedroom, six-bath, 17th-century ocher-and-cream palazzo called La Favorita. It was located just outside Marsala, a few minutes’ drive from the coast. At $8,500 a week, it was beyond our maximum, but the price included a full-time staff: maid, butler, even a cook. (The cost of La Favorita now starts at roughly $10,000 a week.) And judging from the photos, the place had character to burn. Plus, the owner was a countess—a countess! How could we go wrong?

Take advantage of the agency’s expertise.

The best agents are there to help, not only to sell—functioning less like real estate agents than travel concierges. Four weeks before our departure, a two-pound info packet arrived by mail, containing Think Sicily’s own 192-page A Portrait of Sicily guidebook; a road map; and a thick spiral-bound booklet of orientation materials specific to our villa, including a plan of the Palermo airport, directions to the house (with helpful photographs of tricky intersections), tips for driving in Sicily (more nerve-wracking than you’d imagine), a handy glossary, menu suggestions from our chef, and instructions for everything from trash disposal to how to operate the air conditioners.

Lane, too, was generous with his knowledge, and didn’t object to our peppering him with e-mail inquiries about what to see and do on the west coast. He shared plenty of advice on Sicilian customs and cuisine (we absolutely had to try the busiate con pesto trapanese with shrimp and sea urchin at Fior di Sale, just north of central Marsala) and offered to arrange excursions for our group (Marsala wine tastings; a sailing trip to the Egadi Islands). None of this felt like up-selling, but rather like the enthusiastic recommendations of a veteran insider. Having lived in Palermo for 14 years, Lane knows the island better than most Sicilians.

Pack perspective and a sense of humor.

No matter how much advance research one does, there are bound to be some surprises upon arrival, as well as a certain degree of letdown. The first surprise we encountered at La Favorita? The owner herself was staying in the neighboring guest cottage while we rented the main house—a detail that Think Sicily had neglected to mention.

Contessa Elisabetta was indeed Palermo nobility; her ancestors had used the estate as a hunting lodge in the 1600’s. Back then the property stretched clear to the coast, with only fields, forest, and wild game in between. (Elisabetta apologized for the general decline of Marsala in the 400 years since.) La Favorita still enjoys relative tranquillity on its four-acre plot, with long, shady allées of olive and lemon trees.

As for the house itself, “character” didn’t begin to describe it. Every room contained a hundred things to gaze upon and wonder over, such as the study filled with the mounted heads of long-dead African mammals and one menacingly tusked cinghiale. Or the library littered with coral, starfish, sponges, and horseshoe crabs. Scary-looking swords dangled over the foyer. A flock of stuffed birds had colonized the den. At every corner we met another of the contessa’s ancestors, staring out from smoke-blackened canvases—fierce-eyed men named Eustachius or Bernardus, clad in armor and peacock plumage. The place felt like a natural-history museum crossed with a haunted mansion from Scooby-Doo.

Can a villa have too much personality? This one sort of did. For every elegant detail (hand-painted tile floors; a 30-foot Persian rug), there were equally egregious design choices (a kooky coral candelabrum; acid-green upholstery). It was, in short, the home of a long-standing aristocratic family, one with so much wealth and stature that nobody ever called them out on their eccentric taste.

Staff can be an asset and a challenge.

Some find the very idea of butlers, maids, and personal cooks ostentatious. Others worry they’ll just get in the way. Both have a point. But a fully serviced house can offer real advantages, if you manage expectations—your own and the staff’s.

Our first 24 hours were consumed with the awkward task of making ourselves at home: puzzling over window latches, figuring out light switches, worrying about that weird metal tube protruding from the fireplace. But our main concern was dealing with the contessa’s staff. On paper it had sounded idyllic. Davide, the majordomo, would serve our meals and look after the house; Maria would come each morning to clean; and Daniela was in charge of the cooking. All three could help with our friends’ two-year-old son, Rainen. Downside? None of the staff spoke fluent English. (Another key detail that Think Sicily neglected to mention.) Daniela, however, was fluent in French, as is my wife. So it fell to Nilou to speak for us.

The contessa, meanwhile, kept popping by unannounced, making us feel like houseguests rather than masters of our domain. She eventually picked up on this and made herself scarce—but even then her presence was felt. Daniela would invoke “Madame” whenever we departed from protocol. The contessa apparently had strong opinions about which china was appropriate for pastry, which wine went best with lamb, and when breakfast should be served (8:30 a.m. sharp—never mind that our jet-lagged crew was unconscious till 10). “Mais Madame dit…!” Daniela would say, frowning. But Madame says…!

By day three, we were feeling a bit thwarted by the specter of the bossy contessa. When Daniela once again brought up “Madame,” Nilou delicately replied, “Pour cette semaine, nous sommes Madame.” (“This week, we are Madame.”) Daniela finally got it—and from then on, she deferred to our wishes over Madame’s. The mood of the house notably relaxed, and during the second half of the week, the staff actually seemed to enjoy our company.

Don’t underestimate the power of the market.

One thing that Davide and Daniela could never quite fathom: why we would all voluntarily pile into our cars each morning and head off to market, rather than lounge by the pool and let the staff run the errands instead. But they didn’t understand—shopping for groceries was one of the highlights of our day.

Marsala’s food market sets up near the Porta Garibaldi, in the heart of the city’s old town. Dark canopies shield the fishmongers’ ice troughs from the searing Mediterranean sun. Since there are few people in Marsala who don’t live in Marsala, we couldn’t help standing out. By Tuesday we had become quasi celebrities. At Da Pasquale, the butcher would wave when we approached; produce vendors offered us free samples—peppery fennel fronds, tart fragole selvatiche (wild strawberries). That storied Sicilian reserve quickly dropped away. Old women counseled us on which of the five varieties of melanzane (eggplant) were best for baking versus frying. An amiable Tunisian herbsman spent 20 minutes with Nilou, outlining the subtleties of his basil. Later that day he friended her on Facebook. Operation Sicilian Embed: successful!

Let the cook cook.

We’d originally planned on making most meals ourselves, but we soon surrendered the stoves to Daniela. Her cooking was hearty, soulful, authentic—and exactly what we craved. I still miss her melanzane parmigiana, her roast spring lamb, her spaghetti con bottarga, her pasta con le sarde (that ur-Sicilian dish of bucatini, sardines, wild fennel, pine nuts, and raisins). Our meals were served outside, under a violet-flowering jacaranda tree. Davide set out fresh-cut white roses alongside the contessa’s wacky coral centerpieces, which never failed to amuse us.

The highlight meal of the week, however, came the night of my birthday, when we finally moved inside to La Favorita’s grand, over-the-top dining room. Hung on one wall was a massive 10-foot-high oil painting of the contessa’s family tree, starting in the 14th century. Davide had spent the afternoon secretly installing LED lights (yes, LED lights) under a plexiglass tabletop, which he then disguised under a white tablecloth. When we walked in to take our seats for dinner, he hit the switch—and we got our first delighted look at what we now refer to as the Disco Table.

Daniela, meanwhile, had prepared her tour-de-force dish of couscous di pesce, a specialty of western Sicily: fluffy, savory couscous mixed with calamari and shrimp, served alongside pan-roasted grouper and scorpion fish. Daniela had worked the entire morning rolling the couscous by hand. The meal was extraordinary. We gave her a standing ovation.

Learn to stay put.

“Our American clients generally want to get out and explore,” Think Sicily’s Huw Beaugié says. “They want to see the temples, the salt pans, or where granddad was born. Whereas European visitors tend to view Sicily as just another seaside destination. They’re happy to sit by the pool and never leave the house.”

We fit squarely in the first category. Our first three days were spent in a sightseeing panic, as we caravanned up and down the coast—visiting the windmills and salt lagoons north of Marsala; wandering the dusty Tunisian quarter in Mazara del Vallo; touring the ruins at Selinunte and Segesta. We rode a cable car to the mountaintop village of Erice (with its spectacular Mediterranean views and cobblestoned lanes, resistant to right angles), and found the finest cannoli I’ve ever tasted at Pasticceria Maria Grammatico. One evening we drove an hour inland, through undulating pastures full of sheep, to a remote hilltop restaurant called Ardigna, near Salemi, where nearly everything is made in-house: tangy ricotta, fragrant wildflower honey, garlicky salumi, silky tagliatelle, bittersweet amaro. The bill for our nine-course, six-hour dinner? Just under $50 a person.

And we lost ourselves on the back alleys and coastal promenades of Marsala, from whence Garibaldi and his thousand Red Shirts began their campaign to unify Italy. With its sunbaked, dun-colored façades, Marsala looks and feels closer to North Africa than to mainland Italy—which, in fact, it is. (The name comes from the Arabic Mars el-Allah, meaning “port of God.”) Beyond the market and the old town, however, the city’s outskirts are given over to canning plants, used-car lots, and drab concrete housing blocks. It has a certain sense of place, I guess, but it’s no Positano.

At a certain point we realized we were happiest enjoying the villa itself. “Oversleep, underplan” became our new motto. Aside from the morning market run and an evening foray for gelato, we stuck close to home: strolling in the garden, leafing through the contessa’s complete works of Rousseau, playing carambola on the 14-foot billiard table. Two-year-old Rainen preferred to hang out in the taxidermy room, gazing up at the gazelles.

All around the house were framed photos of the contessa’s contemporary family—at the dining table, by the pool, at the tennis court—looking like, well, nobility. (We came to refer to them as I Royal Tenenbaumi.) At the end of the week it struck us that we had re-created those very scenes ourselves, almost to the letter. We’d even started dressing for dinner.

For travelers with children, a house always trumps a hotel.

La Favorita could have felt overly stuffy and formal, but having a two-year-old in residence definitely lightened the vibe. And of course the villa offered obvious advantages for his parents: Rainen could have full run of the place, make as much noise as he liked, eat whenever he was hungry, and nap without interruption.

On our second morning we welcomed an unexpected visitor: the contessa’s adorable dachshund, Brisley, who turned up at our breakfast table, sniffing at his strange new guests. There’s nothing like a dog to make you instantly feel at home. And, of course, Rainen was smitten. Watching him and Brisley chase each other around the garden—and the backyard, the living room, the kitchen, and the library—kept us endlessly entertained. That dog was ridiculous.

Sometimes the things that throw you off become the very things you’ll miss the most.

So the week had its share of snags and disappointments. Inserting ourselves into an already functioning, fully serviced household hadn’t been easy. The contessa’s presence during our first few days was disconcerting at best. And the house itself really was spectacularly weird. Yet when we look at the 2,137 photographs taken during that too-fleeting week, it’s those kooky details and disarming moments that invariably make us laugh out loud and render that time so memorable.

Setting out for Sicily, we thought we’d studied, scouted, and planned for every outcome. But really, who could have imagined, let alone made up, a house as comically strange as La Favorita? Or a town as quirky as Marsala? Forget Positano, or any of those other, prettier places: this was even more transporting. Life at the villa essentially became a weeklong role-playing exercise. For seven days we tried on another family’s life—quite literally taking their place, like understudies in some aristocratic theater of the absurd. And La Favorita, so chock-full of character, in turn became a character—along with Daniela and Davide, the Tunisian herbsman, Pasquale the butcher, the contessa and her medieval ancestors, and, of course, Brisley the dog—in our delightfully odd, quintessentially Sicilian play.

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