How to Travel the 2026 Winter Olympics Like an Italian Insider
The 2026 Winter Olympics represent something unprecedented: a Games staged not in purpose-built alpine infrastructure, but across five distinct Italian destinations, each with centuries of hospitality tradition and cultural weight that no Olympic host has previously offered. Italy, characteristically, decided one venue wasn’t enough—because why stick to a singular domain when you can sprawl across Lombardy and Veneto in spectacular fashion?
From February 6 through 22, the world’s attention turns to northern Italy, and the savvy traveler’s opportunity extends well beyond the competition schedule. Milan, hosting the Opening Ceremony at San Siro, has quietly transformed into a luxury hotel destination capable of rivaling Paris and London—with a dining scene that finally matches its fashion credentials, after decades of playing catch-up. A two-hour drive northeast (or 90 minutes, if your driver shares the local disregard for speed limits) delivers you to Cortina d’Ampezzo, where the “Queen of the Dolomites” returns to Olympic glory for the first time since hosting the 1956 Games, which introduced the world to live international television broadcasting.
Continue northwest through the Stelvio Pass—one of the Alps’ most legendary driving roads, with 48 hairpin turns—and you’ll reach Bormio, which offers something no other Olympic venue can claim: 2,000 years of thermal bathing tradition, alongside the world’s most technically demanding downhill course. Another hour through mountain tunnels brings Livigno, the duty-free anomaly where Napoleonic-era tax exemptions mean 22 percent savings on everything from Gucci to Barolo. And Verona, a 90-minute train from Milan, closes the Games inside a Roman amphitheater that predates Christianity, surrounded by three-Michelin-star dining and wine country producing Italy’s most collectible reds.
This is a guide to experiencing these five destinations as an insider: where to stay, what to eat, which bars matter, and how to navigate the intersection of athletic competition and Italian hospitality that makes Milano Cortina 2026 unlike any Winter Games before it.
The 2026 Winter Olympics, the Italian Way
- Milan transforms into the world’s most fashionable Olympic gateway
- Where Milanese insiders wine and dine
- The cocktail bars that matter
- Shopping in the world’s most expensive retail corridor
- Cortina d’Ampezzo reclaims its throne as Europe’s most glamorous alpine destination
- Dining and drinking where the mountains meet the plate
- Bormio delivers authentic alpine luxury with thermal heritage
- Livigno combines duty-free luxury with freestyle spectacle
- Verona stages the closing act in a 2,000-year-old amphitheater
Milan transforms into the world’s most fashionable Olympic gateway
Milan hosts the Opening Ceremony at San Siro stadium on February 6, with performances by Mariah Carey, Andrea Bocelli and Laura Pausini. But the real story is the city’s metamorphosis into a genuine luxury hospitality destination—one that can finally rival Paris and London for hotel obsessives. The established pillars remain Four Seasons Milan, the converted 15th-century convent on Via Gesù that still delivers the city’s most consistent five-star experience, and Mandarin Oriental Milan, steps from La Scala. Both are Gruppo Statuto properties—the dynasty that also controls Hotel Danieli in Venice—and both will feel the competitive pressure of what’s coming. The Carlton by Rocco Forte reopened in November 2024 as the play for cocktail devotees: legendary mixologist Salvatore Calabrese runs the Carlton Bar, while Fulvio Pierangelini handles the kitchen. The suites occupy Via della Spiga’s most coveted stretch, making this the recovery address after long days navigating the Quadrilatero. Another option just down the street is Portrait Milano, from the Ferragamo family. Casa Brera, a Luxury Collection Hotel, suits those who prefer Brera’s gallery-and-aperitivo energy to the fashion district’s commercial intensity; the year-round rooftop pool doesn’t hurt. For travelers timing visits post-Olympics, Rosewood Milan and Six Senses Milan are the most significant openings through the rest of 2026.
Where Milanese insiders wine and dine
Milan’s fine dining scene has finally caught up with its fashion credentials. Enrico Bartolini at Mudec holds the city’s only three Michelin stars—the first Milan has seen since Gualtiero Marchesi’s legendary restaurant closed in 1993. The two-star tier offers more interesting dining for those who prefer counter seats to white tablecloths. Verso Capitaneo, where the Capitaneo brothers earned their second star in 2024, puts you directly on Piazza Duomo, with dishes like blue lobster with yellow courgettes and rose of red beetroot petals with caviar. But the restaurants generating genuine local heat operate well below the starred stratosphere. Trippa remains the reservations nightmare every food obsessive should attempt: chef Diego Rossi’s modern trattoria honoring offal releases bookings on the first of each month at noon and sells out within hours. Cucina Franca is the anti-Bartolini proposition—a short, plant-forward menu where the six-course tasting runs under $50. For the creative class, Sandì on Via Hayez occupies a former 1960s bakery with weekly-changing menus and natural wines poured by Parasite 2.0’s design collective.
The cocktail bars that matter
Two historic bars anchor any serious Milan drinking itinerary. Bar Basso on Via Plinio is where Mirko Stocchetto invented the Negroni Sbagliato—the exact year remains charmingly disputed, though regulars place it somewhere around 1968 or 1972, when he reached for Prosecco instead of gin and created a cocktail that would go viral five decades later. Camparino in Galleria offers the opposite energy: a shrine to Campari opened in 1915 by Davide Campari himself, where you drink beneath original mosaic tiles with the Duomo visible through arched windows. Arrive around 6 p.m. and order the Campari Seltz and nothing else. For those who’ve done the classics and want discovery, Bar Nico on Via Cesare Saldini has become the city’s hardest-to-find essential—a no-reservations natural wine bar by former fashion duo Chiara Pino and Riccardo Ganelli. Look for the red light behind a faded “Pastificio” sign; there’s no other indication you’ve arrived.
Shopping in the world’s most expensive retail corridor
Via Montenapoleone officially surpassed Fifth Avenue in 2024 to become the world’s most expensive retail corridor, and the transformation is visible at street level. Louis Vuitton reopened at Palazzo Taverna in April 2025 with two in-house restaurants, including a Milanese outpost of the Cerea family’s legendary Da Vittorio. Directly opposite, Fendi unveiled a multi-floor flagship with a leather goods atelier where you can watch artisans work. Saint Laurent doubled its footprint, with Anthony Vaccarello’s signature marble and eucalyptus interiors creating the moodiest fitting rooms in the Quadrilatero. The cultural counterweight is Fondazione Prada, a 20-minute taxi south to the former distillery Rem Koolhaas transformed into one of Europe’s most ambitious contemporary art spaces. The collection is reason enough, but insiders come for Bar Luce—Wes Anderson’s commission recreating a vintage Milanese café, complete with working pinball machines and Formica tables. For those whose appetites run toward Old Masters, the Grande Brera expansion at the Pinacoteca finally realizes the museum’s long-planned contemporary galleries—a proper excuse to revisit Mantegna and Raphael before wandering into spaces that now rival Brera’s commercial galleries next door.
Cortina d’Ampezzo reclaims its throne as Europe’s most glamorous alpine destination
Cortina d’Ampezzo returns to Olympic competition, hosting women’s alpine skiing, bobsled, luge, skeleton and curling events. It’s the region’s first Games since 1956, when RAI’s live broadcast introduced the world to televised Winter Olympics. While the town has spent decades trading in postwar glamour, the hospitality landscape is finally catching up to the scenery. Mandarin Oriental Cristallo Cortina represents the most anticipated opening of 2026—and the most dramatic resurrection. The Grand Hotel Cristallo is where Frank Sinatra and Brigitte Bardot held court during Cortina’s Dolce Vita peak; Herzog & de Meuron’s sweeping renovation promises the brand’s signature layered interiors rendered in alpine materials. For those who can’t wait, Hotel Ancora is ready to book. Diesel founder Renzo Rosso acquired this 1826 property, then handed interiors to former Soho House design director Vicky Charles. The real draw is the terrace overlooking Corso Italia—the sunset position for Cortina’s passeggiata ritual, where the town’s social hierarchy reveals itself nightly over Aperol spritzes. The First Hotel Cortina opened in late 2025 as the sustainable luxury play, with glass panels framing UNESCO-protected Dolomite peaks from nearly every angle. For ultra-luxury devotees willing to drive 30 minutes, Aman Rosa Alpina in San Cassiano offers the brand’s signature silence and space.
Dining and drinking where the mountains meet the plate
Cortina’s dining splits between Michelin-starred establishments and rifugio experiences you can’t replicate anywhere else. Tivoli has held its star for over 30 years under chef-owner Graziano Prest; request the window tables for picture-postcard Dolomite views. Seven-table SanBrite is where chef Riccardo Gaspari earned his star by serving almost exclusively what his family produces on their alpine farm—mountain-pine-flavored spaghetti and milk-and-larch-buds gelato define hyperlocal cooking pushed to its extreme. The experience that no starred restaurant can match is Rifugio Mietres, where at 5,600 feet, an outdoor hot tub in larch wood sits on the sun terrace. Dine, then soak while watching the enrosadira—the pink-orange glow that illuminates Dolomite peaks at sunset. Bar del Posta at Hotel de la Poste has anchored Cortina’s social life since 1835. Hemingway’s regular corner remains preserved; order the Puccini, the mimosa-like signature, and settle in. The après-ski scene offers two energies: Chalet Tofana brings international DJs on weekends against pink-lit Dolomites, while Super G Faloria Mountain Club answers with club culture on a terrace suspended among the peaks.
Bormio delivers authentic alpine luxury with thermal heritage
Bormio hosts all men’s alpine skiing on the legendary Stelvio slope—considered one of the world’s most technical downhill courses—and makes history with ski mountaineering’s Olympic debut. But the real reason to base yourself here isn’t the racing. Bormio sits atop nine natural thermal hot springs, drawing on 2,000 years of bathing tradition first documented by Pliny the Elder. QC Terme Bagni Vecchi dates to Roman times, with medieval, imperial and archduchess baths carved directly into rock. The San Martino Spring offers a natural sweat cave unlike anything in the modern spa world; the infinity pool delivers panoramic valley views. For those who want the baths without leaving their hotel, QC Terme Grand Hotel Bagni Nuovi provides direct room access to thermal circuits across a restored Art Nouveau building, where you can shuffle from bed to Roman bath in a robe. Eden Hotel Bormio suits the design-conscious crowd: interiors by Antonio Citterio and Patricia Viel, with chef Giovanni Caracciolo running a modernist fine-dining program he describes as influenced by Jackson Pollock.
Livigno combines duty-free luxury with freestyle spectacle
Livigno exists in its own economic universe: a Napoleonic-era tax quirk grants VAT exemption on all goods, which translates to roughly 22 percent off luxury retail without the airport duty-free fluorescent lighting. The town hosts freestyle skiing and snowboarding in a Snow Park designed so spectators can watch halfpipe, slopestyle, ski cross and snowboard cross from a single vantage point. Hotel Lac Salin Spa & Mountain Resort leads the luxury tier, with a spa built around medicinal mountain herbs and the signature Snow Spa—each winter, artist Vania Cusini sculpts an ice spa with an outdoor jacuzzi that exists only until spring melt. It’s gimmicky in the best possible way. Livigno claims more than 150 bars; an improbable density for a town of 7,000, explained entirely by duty-free alcohol. Kosmo Taste the Mountain holds Michelin Guide recognition for contemporary alpine cuisine—the closest Livigno comes to fine dining, and worth the reservation.
Verona stages the closing act in a 2,000-year-old amphitheater
The Closing Ceremony on February 22 at the Arena di Verona provides the theatrical conclusion these Games deserve. Better yet, no previous Winter Olympics has featured a 2,000-year-old Roman amphitheater. Creative director Alfredo Accatino’s “Beauty in Action” expands beyond the Arena into Piazza Bra and Teatro Filarmonico, with confirmed headliner Roberto Bolle. Due Torri Hotel remains Verona’s most distinguished address: a Leading Hotels of the World member occupying a 700-year-old building on Piazza Sant’Anastasia. NH Collection Palazzo Verona offers history layered on history—a 14th-century palazzo built around visible Roman ruins, with original frescoes intact. Palazzo Monga Boutique Guesthouse suits travelers who prefer intimacy: just three suites in a grand 18th-century palazzo with chandeliers that feel borrowed from a Visconti film.
Casa Perbellini 12 Apostoli brought three Michelin stars back to Verona when chef Giancarlo Perbellini reopened this historic space in 2023. Designer Patricia Urquiola’s renovation preserves frescoed ceilings and Roman ruins in the basement. Il Desco maintains its single star with playful touches, like “Scallops Pulp Fiction,” that signal a kitchen that doesn’t take itself too seriously. Verona sits at Valpolicella’s doorstep, which means wine drinking is obligatory. Antica Bottega del Vino, established in 1890, holds 4,500 labels and serves the definitive risotto all’Amarone. For aperitivo, Mandorla draws locals with natural wines and standing-room conviviality; Terrazza Bar al Ponte offers Adige River views until 2 a.m. Valpolicella wine country lies 20-30 minutes away, with more than 300 wineries producing Amarone (the collectible) and Ripasso (the value play).
As for Casa di Giulietta: the medieval tower house on Via Cappello 23 receives 50,000-plus letters addressed to “Juliet, Verona, Italy” annually. The famous balcony was added during a 1928 restoration; the bronze Juliet statue dates to 1972. The bed and original costumes from Franco Zeffirelli’s 1968 film are on display. Crowds are intense, especially around Valentine’s Day, and online booking is now required. Whether this constitutes essential cultural tourism or Instagram-driven spectacle depends entirely on your tolerance for Shakespeare-adjacent commerce. You’ve been warned.