When you first enter Terre di San Giustino, a manicured estate tucked away in the Tuscan hills of Monte San Savino, the house is nowhere to be seen. You meander past an olive grove, a private vineyard, and through a tunnel of cyprus trees before getting there. And when you do, the chic property manager, Barbara, is waiting, holding back two wagging Maremma sheepdogs, who are fluffy, irresistible creatures. Behind her, a hospitality staff sets up an array of beverages al fresco: sparkling water with raspberries and blueberries, bubbling prosecco, red wine made from their Sangiovese grapes. In the kitchen, the private chef works on perfecting his almond cake. Roses crawl up the walls of the earth-stone villa, and lavender bushes dot the property’s periphery. An infinity pool with white cabanas extends into the bucolic horizon.
Welcome to Airbnb Luxe.
Today, Airbnb launches its new luxury tier, which, as cofounder and CEO Brian Chesky tells Vogue, is “a selection of the world’s most extraordinary places to stay.”
Luxe is a long-anticipated project. Rumors of it started in 2017, after the company acquired Luxury Retreats, an upscale vacation rental company with a plum inventory. In 2018, Airbnb confirmed the news in a keynote presentation. Now, after almost 18 quiet months, there are 2,000 sparkling new properties available for booking in dozens of locations: Bali, Lake Como, the Swiss Alps, St. Barth’s, Amalfi, Santorini, and so on.
Airbnb Luxe isn’t just about exceptional homes and locations. Each lodging comes with a Trip Designer, a 24/7 concierge who organizes everything from airport transfers to restaurant reservations, excursions, and weddings. Yes, weddings—“People do tend to travel for special occasions,” says Keith Monaghan, Airbnb’s head of trip design. “We have been involved in wedding planning. We’ve been involved in vow renewals. We’ve done executive retreats, which have been surfing trips in Bali, where you have people with very different levels of ability to surf.”
For the company, catering to special requests is a vital part of the new platform: “We believe luxury travel is changing, and travelers are seeking more transformative experiences,” says Chesky. “With Airbnb Luxe, we are applying the same approach we’ve used since we launched Airbnb more than 11 years ago—creating local, authentic and magical travel moments now in amazing places to stay—to reimagine the way people think and experience luxury travel.”
Lofty descriptors and marketing buzzwords are one thing. But what is it really like to stay at an Airbnb Luxe property? A week before the launch, I set out to discover the answer—and in the process, became the first person to experience the new venture.
First, I needed to pick a place to stay. The options were exciting, to say the least. There were historic accommodations (a villa in Jamaica where Ian Fleming worked on his James Bond novels), exotic locales (a French Polynesian island with its own time zone that rents over $140,000 a night in August), and professionally designed spaces (a Kelly Wearstler house in Beverly Hills). Most have multiple bedrooms, and sometimes even multiple homes—the platform’s offerings are geared more toward group travelers.
I settled on Terre di San Giustino, an idyllic-looking getaway in Tuscany. The four-bedroom property was comprised of a series of stone buildings, each with their own name: Fienile, Scuderia, and La Colombaia. Amenities included an infinity pool, a tennis court, and a courtyard garden with a fountain and giant chessboard. It also came with a chef and housekeeping—a novel step for the company.
And, while we’re talking about cost, I should add that none of this comes cheap: Terre di San Giustino is $7,309 a night (the price goes up and down depending on the season). And that’s not factoring in the add-ons: like activities, grocery pre-stocking, airport transfers, and so on.
The booking process for Airbnb Luxe is different than traditional Airbnb. For a regular Airbnb, you pick a date range, request to book, and a host approves or rejects your request (with perhaps a little chatter in between.) With Luxe, you press a button to “contact a Trip Designer.”
They don’t approve you right away. Instead, they ask you questions: What brings you to this particular location? Who are you traveling with? The reasoning behind this, my Trip Designer tells me, is to make sure it’s the right fit. If you’re traveling as a family, they want to make sure the place is kid friendly. If someone in a group is handicapped, they want to make sure a first-floor bedroom is up to snuff.
For me, she raised the point that Terre di San Giustino was in a remote location—would I, as a solo traveler, prefer something livelier? I explained that an isolated escape was right up my alley.
We mostly instant messaged through the Airbnb app. As a typical millennial who dreads a phone call and loves iMessage and Slack, it was a refreshing way to plan. (Airbnb reports that, in a beta-testing of the Luxe platform, they found 60 percent of bookings were done on mobile.) However, if you’re someone who prefers to plan over the phone, there’s always a number to call.
After confirming that Terre di San Giustino was available during my desired dates, my reservation was approved.
Next up, planning. While most luxury hotels come with concierge services, Airbnb users have usually relied on the advice of their host (or the internet) for activity planning. (In 2016, the platform began to offer custom activities with Airbnb Experiences. But still, the brunt of organization and coordination fell on the guests themselves.)
Not so with Luxe. After a brief discussion of my interests (food, leisure sports), they threw out some suggestions. Truffle hunting, a winery tour via helicopter, a road trip in a vintage car, private tennis lessons, lunch at a Michelin-star restaurant, and a boat cruise on Lake Trasimeno were among the options. I said yes to the first three. “Do you have any suggestions for art excursions in the area?” I typed in my chat box. “I’ve been to all the big museums in Florence. Are there any smaller galleries or collections you’d recommend?” By the next morning, everything I requested was confirmed—and they’d arrange a visit to an Italian palace in Montepulciano, where a noble family still lives.
Eighteen hours of travel later, I arrived at Terre di San Giustino, with its aforementioned olive groves and cyprus trees. To qualify for Airbnb Luxe, each property must pass a 300-point inspection. The test is broken down into five categories: form, function, feel, location, and services.
Form: Essentially, design. The Airbnb team wants high-vaulted ceilings, attractive art, and closets with matching hangers. Vital are what they call “socially enhancing spaces”— “where everybody can see eye to eye and have a chat together,” explains Nick Guezen, director of portfolio strategy at Airbnb. “There should be space for everyone to sit around the dining room table. In the living room, there should be room for enough people to sit around and watch a movie together. Out in the gardens, different seating areas for people to have a drink and chat,” he adds.
Function: Is the air conditioning working? Does the kitchen have enough pots and pans? Is there a favorable bedroom to bathroom ratio? Are there extra pillows and blankets? Is parking available? (For Los Angeles homes, they also check for electric car ports.) Feel: Mood. They want unique attributes, whether it’s distinctive architecture, a statement-making entrance, or picturesque geography. They consider location: Is this home somewhere where you want to be, whether a remote locale or in London’s hottest neighborhood? And services: will you have professional resources at your disposal?
Terre di San Giustino is owned by a couple who live in New Zealand. It’s a classic Tuscan farmhouse with warm earth-tone stone walls adorned with ivy and red shutters, tile floors, and rustic wood-beamed ceilings with brick archways. The vineyard produces its own wine and olive oil. Once upon a time, it had horses. The equines are long gone—the stable turned into a guesthouse—but chickens and the two aforementioned Maremmas, Milo and Elsa (and occasionally, a dachshund named Francesco), wander the grounds. The garden is filled with signature Tuscan flora: lavender, sage, rosemary. A fountain bubbles in the middle of it.
As I wander through the estate, I make a mental note of all the 300-point items I can spot. Picturesque geography? Check—it’s of the vineyard and rolling hills beyond. Socially enhancing spaces? Check—there’s a courtyard with outdoor furniture, an expansive dining table, and a delightful alfresco dining area called The Summer Kitchen. Working appliances? Check—the pool is heated, the hot water is running, and the coffee machine pumps out a mean cappuccino. And yes, my closet does indeed have matching hangers.
My host, Barbara, was there throughout my stay. While my Trip Designers gave me updates about my itinerary and checked in daily, Barbara was my on-the-ground point person.
An Airbnb host is a pro or a con, depending on who you ask. Some people love them because they find joy in meeting new people, and are interested in the host’s knowledge about the local community. Others just want to be left alone on a vacation, and don’t want a reminder of whose towels they’re using.
But with Airbnb Luxe, your host is, well, a professional. Barbara is Terre di San Giustino’s property manager and on-site concierge. She oversees the home, the vineyard, and coordinates with the owners, Airbnb, and the guests. She speaks multiple languages and could moonlight as a wine connoisseur if she wished. She’s on hand to make sure everything runs smoothly: that breakfast is served at the right time, and the tennis instructor can find the home. Plus, she made a delicious welcome basket, full of Italian goodies like breadsticks, olive oil, and jam.
While Barbara made me feel fully at home at the villa, most of the day was dedicated to various excursions. Regular Airbnb “Experiences” are billed as “one-of-a-kind experiences hosted by locals.” With Luxe, add over-the-top to that description.
Take the must-do Tuscan activity: wine tasting. I did that! But I journeyed from vineyard to vineyard in a helicopter. And my guide, wine sommelier Filippo Bartolotta, had shown the Obamas around the region two years ago. The wineries I visited were top-notch: like Castiglion del Bosco, owned by the Ferragamo family and the recent site of Caroline Wozniacki’s wedding, or a biodynamic farm owned by the Illy family. I also toured medieval towns in the region—but in a forest green Morgan automobile and while eating sheep’s milk gelato.
After days spent exploring, I returned to my Terre di San Giustino, where gourmet dinners awaited: one night, I learned how to make pasta. Another night, I enjoyed a five-course tasting menu which included tomato chutney and pea biscuits, grilled seafood sausage with sea bass, mango and ginger lime sorbet, grilled fillet with parmesan croquettes, and orange Crème br?lée. Oh, and lots of prosciutto to start.
Luxury group travelers have a lot of options. They can book upscale residences through hotel groups like the Four Seasons, rental companies like Onefinestay (which has “trip advisors” and “home managers”) or high-end vacation clubs like Exclusive Resorts, which has “vacation ambassadors” who act as on-site concierges, as well as membership perks.
So where does Airbnb Luxe fall into all of this?
The company has always prided itself on its authenticity. You don’t visit a city with Airbnb, you immerse yourself in it. (“We imagine a world where every one of us can belong anywhere,” Chesky wrote in 2018.) It’s part of the fun: When I visited San Francisco last year, I stayed in a Bernal Heights apartment above a cannabis dispensary. Everything was immaculate and everything also smelled faintly of weed. My hosts, who worked at said cannabis dispensary, gave me CBD products and advice on where to get the best burrito.
I was wondering if that sense of immersion would be lost with Luxe. Luxury caters to comfort, and oftentimes comfort means not leaving, well, your comfort zone. Everything can become standardized and sanitized—it’s easy to end up eating off menus that reproduce what you have at home, doing tried-and-true tourist activities, staying in rooms that look like they could be anywhere in the world. Would Airbnb lose what, to me, makes it so special—wild and wide-ranging uniqueness—in its quest to capitalize on the high-end market and its often persnickety, demanding guests?
Guezen brought up a part of the checklist that is a little hard to explain. “Does it tell a story while you’re there?” he said. “Is it about tranquility, or is it about excitement? Is there a narrative in the home?”
As I sat on the lawn of Terre di San Giustino drinking Brunello and playing with the Maremma sheepdogs, a breed only found in Tuscany, I understood what he meant. The “story” that this house told was one of the local culture. Even with all its bells and whistles and chef-grade appliances, this place made me feel like I lived in the Italian countryside, albeit briefly. Amid the many requirement boxes, that’s the one that, to me, makes all the difference.