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.
Day 2: Bormio to Merano (62 miles)
Although it’s the shortest drive on the itinerary, day two’s serpentine route requires the concentration and maneuvering of a Formula One race car driver. Outside Bormio, the S38 heads up the precipitous slopes of the Passo dello Stelvio, the second-highest mountain pass in the Alps. As you crest its 9,000-foot summit, you’ll face a dizzying descent with 48 hairpin turns. Once you’re down the northern side, make a left onto the S40, then again onto the S41, to the 12th-century walled village of Glorenza. It’s worth a stop if only to tour the Tauferer Tor Turm, a medieval tower housing rotating art installations and a year-round exhibit of the town’s storied past. Back on the S38, turn east toward Merano, a mountain-ringed city that—thanks to its low elevation—has a mild climate and miles of apple orchards and vineyards. Along its pedestrian-only Via dei Portici, you’ll find everything from stylish clothing boutiques and leather shops to sidewalk cafés and delicatessens offering savory speck and smoked bacon. High above town, Castel Fragsburg (3 Via Fragsburg; 39-0473/244-071; dinner for two $136) turns out locavore dishes such as grilled fillet of Tyrolean ox and goose liver accompanied by a tonka-bean brioche. One of the few modern hotels in the area, the Matteo Thun–designed Terme Merano (9 Piazza Terme; 39-0473/259-000; hoteltermemerano.com; doubles from $275) has a funky lobby decorated with electric-red leather chairs and gold-plated faux taxidermy.
Day 3: Merano to Cortina d’Ampezzo (82 miles)
Just south of Merano, hop on the E45 north to the S242, passing the emerald-green Val Gardena valley and into Corvara. This mountain town is chockablock with German-influenced chalets and bordered by the jagged peaks of the Dolomites. At the rustic La Tambra (2 Sassongher Strasse; 39-0471/836-281; lunch for two $40), local meats are the house specialty: Try the pork cheeks in a red-wine reduction and the beef carpaccio. Continue toward the skiing village of Cortina d’Ampezzo, where hikers come to scale the town’s sheer spires of limestone. You can explore the craggy outcroppings via the moderate Sentiero Ivano Dibona trail, which has a network of ladders and ropes to make climbing easier. Cortina has several top-notch lodges, but the newly renovated Grand Hotel Savoia (62 Via Roma; 39-0436/3201; grandhotelsavoia.it; doubles from $490), with its rich wood-paneled rooms and contemporary furnishings, is the most impressive.