With the 2026 Winter Olympics underway in Italy, navigating Milan and Cortina — and securing the most coveted reservations — comes down to one thing: who you know. As the first Games anchored by two primary host cities, Milano-Cortina is also among the most geographically expansive Games in history.
“It is nearly a 500-mile spread between all the venues — Milan, Cortina d’Ampezzo, Livigno, Verona,” says Tiffany Layne, founder of LaVon Private Luxury, elite travel architects tells The Hollywood Reporter. “This is where accommodations and transportation will become highly important.”
Milan, the capital of Lombardy and host of the opening ceremony, is the main location for ice skating (where the world witnessed a gravity defying performance by Ilia Malinin, with Team USA clinching gold in figure skating), along with hockey and speed skating. A four-to-five-hour drive north, Cortina d’Ampezzo takes center stage for alpine skiing and curling, with other competitions being held in smaller towns throughout Northern Italy, including Verona, home to the closing ceremonies on February 22nd.
Given the vast scale and the difficulty of the logistics, tapping an industry-beloved travel designer is essential for anyone hoping to navigate the Games in style. Fortunately, Layne and the travel virtuosos below are unlocking a glimpse into their prized Black Books for THR.
Milan
Lodging + Leisure
With its metropolitan connectivity, Milan has emerged as the hub for Games-bound travelers. “For convenience, most luxury travelers are positioning themselves there, at top hotels like Mandarin Oriental and boutique properties that provide a bit more privacy and intimacy like Vico Milano. Four Seasons Milano is also very popular,” says Layne.
According to Italy’s consummate A-list insider, Fulvio De Bonis, The Carlton, A Rocco Forte Hotel and Portrait Milano are also among the city’s finest for those with discerning tastes. “The latter is a former 16th-century Archbishop’s seminary, largely unused for decades, with its beautiful internal courtyard hidden from the city,” he tells THR.
As CEO and Founder of Imago Artis Travel, De Bonis has designed bespoke experiences for titans of sports and entertainment including Tom Brady, Christian Bale, Jason Momoa, Michael Jordan, Viola Davis, and Oscar Isaac. Yearning to visit the Duomo minus the wall-to-wall crowds? De Bonis is your guy. “We arrange private visits, including the terrace, where you’ll be treated to the best views in the city along with areas of the Duomo that are not open to the general public.” This same level of access extends to Milan’s cultural, bucket-list icons. De Bonis unlocks unparalleled entry to destinations like La Scala and Santa Maria della Grazie, the site of Leonardo da Vinci’s The Last Supper. “We make the impossible happen for our guests.”
Dining + Nightlife
Coveted restaurant reservations are always in demand, but Layne notes that private hospitality suites are the real power move during the Games. “Clubhouse 26 is the main one and will have outposts in Milan and Cortina with menus curated by renowned Italian chefs.” Access is tight, often controlled by a single operator with packages typically purchased in advance.
For De Bonis, the Brera district is a must-visit for dining (he loves Il Solferino) and a leisurely stroll. “This is where Milan feels most authentic. There’s a quiet elegance to it — art, history and everyday life all flowing together,” he adds. And not to be missed is coffee or cocktails at Moebius — “it’s the most iconic and fashionable.” As far as nightlife, one spot claims the crown. “The place to be seen,” adds Layne, “is Philipp Plein Milano for sure.”
Cortina d’Ampezzo / The Dolomites
Getting There
While they’re more under the radar than industry-frequented favorites like Tuscany, Puglia, Sicily and the Amalfi Coast, the Dolomites are Italy’s next mega travel destination according to De Bonis. “It’s a paradise of pristine mountains and meadows, not only in winter, but especially in spring and summer.” And the onslaught of reservations is well underway. “The Dolomites are exploding; we’re booking so much travel there this year.”
Cortina d’Ampezzo is perched in the Veneto region and can be reached from several major gateways, including Venice and Milan, by train or car. Prepare for travel restrictions and checkpoints, though. “The smoothest options will be taking the train from Milan to Venice Mestre, then the Cortina Express bus, with private transfers arranged in advance,” says Agustina Lagos Marmol, owner of Dolomite Mountains, one of the most dialed-in luxury adventure travel company in the area. “Once in Cortina, moving around by hotel shuttle or official transportation will be far easier than relying on private cars.”
Sleep + Play
Of the numerous tycoon-worthy hotels in the region, Layne and De Bonis are particularly enamored with Faloria Mountain SpaResort, located just outside of the town center. “Owner and GM Daniele Colli, a former pro cyclist, embodies the hotel’s deep connection to biking and the outdoors,” says De Bonis. Hotel de Len is also situated close to the action and one of Lagos Marmol’s go-tos.
Our aficionados are also booking guests 50 miles west of Cortina in the South Tyrol region of Alta Badia for a more low-key visit. “Ciasa Salares is one of my favorite hidden gems that boasts one of the best wine cellars in Italy and is family run by Jans Clemens, who has a master knowledge of all things wine,” says Layne. And in adjacent San Cassiano, De Bonis has clients at Aman Rosa Alpina.
Farther out in the western region of Madonna de Campiglio (where Ski World Cup takes place), Lefay Resort & Spa Dolomiti is a haven for wellness revelers thanks to its over 50,000 sq ft spa — ideal as a post Games recharge.
With the help of private alpine guides, adventurous types can indulge in ski safaris (where guests swoosh across multiple mountains over the course of a day or more and visit various rifugios — authentic mountain huts) and even ski with a legend of the sport. “You’ll experience the real Cortina d’Ampezzo alongside Kristian Ghedina, a retired Italian alpine ski racer who achieved 13 World Cup victories and 33 podium finishes,” says De Bonis.
And make time for a “passeggiata” (or short walk) along Corso Italia. “This is Cortina’s main street and is an experience in itself,” says Livia Agnelini of Scott Dunn, high-end vacation specialists. “After skiing, locals, socialites and visitors gather here, creating a vibrant blend of style and tradition for excellent people-watching, luxury boutiques, inviting cafés, and cozy bars ideal for a pre-dinner aperitivo.”
Wine + Dine
With its amalgam of Italian, Austrian and Ladin cuisines, Cortina is home to several Michelin-starred restaurants. “The region has a distinct local culture, blending hearty flavors with refined Italian tradition,” says De Bonis. Think polenta and game meats with such local red wines as Pinot Nero and Lagrein.