Day 1: Milan to Bormio (120 miles)
In Milan, consider renting a Maserati GranCabrio convertible to fully take in the views of Italy’s lake region—you can lease one at Milan’s Malpensa airport from luxury-car outfitter Luxe of Italy (39-0652/279-173; luxeofitaly.com; cars from $733 per day). Leaving the city, get on the S36 north toward Lago di Como and exit the main thruway via the SP72, which traces Lake Como’s eastern shore. The pint-size fishing village of Varenna, a cluster of terra-cotta– and pastel-colored ville that cling to Como’s steeply pitched banks, is the perfect stop for an alfresco lunch. Set in a centuries-old botanical garden, La Contrada (Via IV Novembre; 39-0341/830-113; lunch for two $85) serves regional specialties such as vegetable ravioli with dried-tomato gremolata and mozzarella mousse on a terrace overlooking the lake. After a stroll through Varenna’s tightly coiled streets, it’s back in the driver’s seat: Enter the Alps by way of the S36 followed by the S38, gradually ascending through the bucolic Valtellina valley toward the mountain town of Bormio. During winter, crowds gather to ski the medieval village’s 50-plus trails and soak in its hot springs. But summer brings a different vibe altogether: the throngs disperse and a sleepier alluring ghost town emerges. Check into the 74-room Grand Hotel Bagni Nuovi (doubles from $350), a 19th-century Art Nouveau–style property that’s long been the preferred mountain hideaway of Italian A-listers (soccer star Alberto Gilardino and Bond girl Maria Grazia Cucinotta rank among recent guests). Don’t miss the hotel’s 53,800-square-foot spa, where you can relax in one of 30 open-air thermal baths while taking in the surrounding wooded hills and craggy peaks. For dinner, there’s Al Filò (dinner for two $55), a five-minute drive away. On the menu: potato pizzoccheri (a tagliatelle-like local favorite) expertly prepared by chef Max Tusetti and served in an intimate, stone-walled dining room.