Forget everything you thought you knew about Milan. The Milano–Cortina 2026 Winter Olympics has transformed Italy’s fashion capital into something more, with new cultural spaces, elevated dining, and a vibrancy that makes this the moment to go. Nine hours direct from Atlanta, plus a quick taxi ride, delivers you to The Carlton, Milan — Rocco Forte’s November 2025 debut on Via della Spiga, where 1950s neorealism meets 1980s fashion glamour in authentically Milanese style. Opt for a deluxe suite with a private terrace overlooking the Duomo and the boutiques of Via della Spiga.
Day 1: Fashionable Feat
While Dolce & Gabbana, Gucci, Prada, Versace, and Valentino all launched here, Milan’s real fashion story lives beyond the legacy brands. Start at La DoubleJ for maximalist clothing and homeware crafted by Italy’s finest artisans, then navigate to 10 Corso Como’s pioneering concept space where fashion meets art meets lifestyle.
The Bagatti Valsecchi Museum proves even Renaissance collecting had impeccable taste. These brothers understood curation before it became currency. Continue to Peck, Milan’s legendary gourmet temple since 1883, where the prepared foods counter offers everything from truffle-laced risotto to perfectly composed antipasti plates. Stop at Camparino in Galleria, opened in 1915 within Milan’s spectacular shopping arcade — this is where the Milanese aperitivo ritual became an institution.
Leonardo’s Last Supper at Santa Maria delle Grazie requires your Carlton concierge’s intervention — these tickets are hard to come by. Evening calls for Dolce & Gabbana Martini, their new cocktail and pizza concept that feels more like an installation than a restaurant. Or backtrack to Bar Basso, the cult classic beloved by Milan’s fashion and design crowd — this is where aperitivo hour was born, and their signature negroni variation still draws insiders.
Day 2: The Arts Circuit
Milan’s new art arrives at Palazzo Citterio, showcasing contemporary collections without the Pinacoteca crowds. Continue through Brera’s intimate galleries that feel more like salons, then lunch at N’Ombra de Vin, where wall-to-wall wine bottles create the decor and natural wines pair with housemade salumi.
Afternoon ventures south to Fondazione Prada at Largo Isarco, where Miuccia Prada’s art collection occupies Rem Koolhaas’s striking architectural complex. Break at Bar Luce, the Art Deco-inspired space designed by director Wes Anderson (the sandwiches are divine and supposedly made by Miuccia’s go-to paninoteca — an Italian style sandwich shop).
Evening calls for Diego Rossi’s Trattoria Trippa, where traditional yet creative Lombard cuisine — like Milanese risotto with grilled marrow, vitello tonnato and, of course, the ever present tripe — are reasons it’s booked out months in advance. End at Naviglio Grande’s BackDoor 43, accommodating four people maximum in what resembles an abandoned pharmacy. The 90- minute cocktail sessions feel like theatrical performance art.
Day 3: Old Milan
Start where Milan began, the ancient Ticinese quarter, where Roman columns anchor a neighborhood predating the Duomo by centuries. Walk cobblestones to Chiesa di San Maurizio, Milan’s hidden “Sistine Chapel” where 16th-century frescoes cover every surface in colors that still burn bright.
Continue to Parco delle Basiliche, where locals read under plane trees and twin basilicas frame views stolen from another century. Sant’Eustorgio houses the bones of the Magi in a marble tomb that few discover. Stop at Pasticceria Cucchi for panettone baked using 1950 recipes, then lunch at Bentoteca on Via San Calocero, where chef Tokuyoshi (formerly Massimo Bottura’s sous-chef) serves elevated bento boxes inspired by his childhood.
For dinner, grab a table at Al Pont de Ferr on Ripa di Porta Ticinese for Michelin-recommended creative Italian cuisine with a canal-side terrace that captures old Milan’s romantic essence. After dinner, wander the lamplit canals of the Navigli district where artists’ studios and wine bars spill onto the cobblestones.
Day 4: 36 hours in Franciacorta, Italy's best-kept wine secret
Less than an hour away lies Franciacorta, Italy’s best-kept wine secret — rolling hills between Lake Iseo and the Alps producing sparkling wines that rival Champagne using the traditional method. Check into L’Albereta, the Relais & Châteaux ivy-covered villa owned by Vittorio Moretti of Bellavista winery fame.
Don’t miss breakfast at the hotel’s Stanza 54, where perfect espresso and 360-degree vineyard views stretching to Lake Iseo set the tone for wine
country mornings.
Winery highlights: Ca’ del Bosco is known for its striking architecture and elevated tastings, while Berlucchi launched modern Franciacorta in 1961. CorteBianca leads the organic movement, and Bellavista is celebrated for its Alma Gran Cuvée Brut.
Book Franciacorta Tour for private tours through landscapes where monks first planted vines centuries ago, creating Italy’s most elegant bubbles. Or embrace la dolce vita and rent a Vespa from Iseorent & Automobili Guerrieri to explore at your own pace.
Day 5: Back to Milan
Return to The Carlton, Milan, and check in for one last night, where you’ll take it easy and wean yourself back to thinking about the return with an indulgent
afternoon spa treatment at the hotel. Your last supper means savoring every bite at Paper Moon Giardino, tucked into a 19th-century palazzo in Milan’s Fashion District with its enchanting secret garden. Order their legendary cotoletta or the spaghetto with clams.
