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.