Forget Hotel Buyouts. The Real Flex Is Booking an Entire Town for Your Event

It took a small army of planners, months of red tape, and the cooperation of the local mayor, but finally they had it. The tiny medieval village perched in the hills above Taormina, the tony Sicilian seaside town made famous by the second season of The White Lotus, was theirs.

The lucky couple, and 250 of their nearest and dearest, had completely taken over the village’s two main squares for the evening. A personable pizzaiola dished out pies and ice-cold beers from his small storefront right on the piazza. One nearby restaurant took on antipasti and pasta, another handled entrees and dessert. The village band provided entertainment, and revelers enjoyed wandering around shops that remained open just for them, browsing boutiques with cocktails and glasses of wine in hand. From the balconies of the apartments surrounding the squares, villagers marveled at the spectacle in front of them, dancing along with traditional tunes.

This wedding, in 2017, was the first time the village of Castelmola opened its doors for an exclusive-use event like this, but it’s hardly been the last. In recent years, masters of the universe accustomed to chartering superyachts and buying out resorts have begun extending the logic of exclusivity to entire towns.

Last spring, for instance, the show-stopping, multi-month wedding celebrations of Radhika Merchant and Anant Ambani—estimated to have cost some $600 million—took over the entirety of Portofino’s main square.

But the wedding in Castelmola was more innovative, sparking a trend that’s likely to only pick up steam. It was masterminded by Guido Spinello and Salvatore Lo Giudice—Taormina locals and founders of the luxury local travel company Sicily Lifestyle. Originally, they say, the wedding couple had hoped to throw a street party in Taormina proper. “But the city is a very popular destination,” says Lo Guidice. “It’s not easy to privatize a certain area here because of the number of people, the number of shops. So we started to think about an alternative.”

It was during a walk in the hills above Taormina when it hit them: The hilltop, stone-walled town of Castelmola, with its sweeping views down to the Mediterranean, was perfect. “This is it,” they said.

Since the wedding, they’ve done 30 additional events in Castelmola, the largest being a corporate event for almost 350 people. “We had musicians, painters, the mamma preparing maccheroni, artisans weaving baskets,” says Lo Giudice. “We are always involving more and more local people in showing their heritage, their passion, their history.”

Sicily Lifestyle now has exclusive agreements with the main bars and restaurants in Castelmola’s central piazzas and a very close relationship with city hall and the local authorities that issue all the authorizations to arrange events in public, explains Lo Giudice. And Sicily Lifestyle has partnered with Belmond’s San Timeo Palace and Villa Sant’Andrea and the Four Seasons San Domenico Palace, all in Taormina, to create events, as well.

What guests love about a Castelmola buyout, says Lo Giudice, is the way it lets them “live the kind of experience of being immersed in the local culture.” Thanks to evocative imagery from fashion brands, movies, television, and more, travelers “have a scenario in mind when they think about Italy: small villages, our traditions, our food.”

And it’s not only the local character you’re buying out; it’s local characters, too. Michelle Rago, whose eponymous Manhattan based event and travel company staged a party for 160 guests that took over Castelmola, recalls a Castelmola cook who prepared pasta à la minute and “was the vision of Italian machismo,” while his mother was “exactly like you’d imagine her, wrapped in an apron walking around the tables.”

“We started this because people who want to celebrate something, sometimes they don’t want to be in a space where everything is controlled, or artificial, like an event venue or hotel or restaurant,” Lo Giudice explains. “They really want the experience in a very authentic way.”

But while some come for authenticity, others see a town buyout as an opportunity to indulge in fantasy. For travelers on one of its private jet trips, Abercrombie & Kent hired actors to stage a traditional Sicilian wedding in Castelmola, inspired by The Godfather movies. Meanwhile, New York City–based event producer, stylist, and designer Alexandra Wynne recently organized a three-day celebration in Taormina for clients that began with a “Welcome to Sicily” party in Castelmola, during which traditional musicians in colorful outfits greeted the 150 guests, all of whom wore white, as they awaited the bride- and groom-to-be’s arrival. Once the couple made their entrance, everyone followed the local band into Castelmola’s main square for speeches, dinner, and dancing.

Travel advisor Jack Ezon—cofounder and head of Embark Beyond, who has worked with Sicily Lifestyle on two Castelmola events for clients—says there’s an additional benefit.

“It’s over the top—it’s bragging rights,” says Ezon, who has also organized exclusive use of a town square in the village of Alberobello, in Puglia, for a large dinner party and taken over private isles in the British Virgin Islands for birthdays. “When the town is all yours, you get to connect with the people who are all yours. You don’t get distracted by others being around.”

But the logistics of securing those bragging rights are not for the faint of heart. Beyond partying planning there is safety, security, and not a small amount of property—often ancient—to protect.

“In Italy, bureaucracy it’s still, let’s say, handled in a vintage way,” says Paola Bucci, a Milan-based events specialist with Vicenzo Dascanio, who is widely rumored to have organized and designed the Ambanis’ takeover in Portofino. “Bureaucracy can be really tough and really long.”

Bucci notes that Dascanio’s clients will often commit funds to help support the architectural and artistic patrimony of their event’s location.

But with the right funds and know-how, anything is possible—even in Italy. For one event, not only did Lo Giudice and Spinello organize the takeover of Castelmola, they also managed to orchestrate a buyout of Taormina’s open-air ancient Greek theater, overlooking Mount Etna, for a private concert. Originally, no alcohol was supposed to be served there, says the tech company sales executive who commissioned the event, but Sicily Lifestyle managed to negotiate to have wine. “Only Champagne and white, of course,” the executive says. “No red.”

And although a private concert in an all-but-impossible-to-secure ancient site was supposed to be the highlight of the multi-day event, Castelmola was what all the guests left Italy talking about.

“The Greek theater was wonderful, but everyone talked about how that town was the best part of the trip,” says the exec. “They couldn’t believe we pulled it off.”

By Andrew Sessa