Ilia Malinin of Team United States at the 2026 Winter Olympic Games on Feb. 8, in Milan, Italy. Vittorio Zunino Celotto/Getty Images Share on Facebook Share on X Google Preferred Share to Flipboard Show additional share options Share on LinkedIn Share on Pinterest Share on Reddit Share on Tumblr Share on Whats App Send an Email Print the Article Post a Comment 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." Related Stories News Cheating Olympian's Girlfriend Speaks Out After On-Air Confession: "Hurts to Be in This Position" General News Olympian Tearfully Confesses to Cheating on Girlfriend in "Most Absurd Medal Interview Ever" 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 th