The Dolomites, those inimitable craggy peaks Le Corbusier called "the most beautiful work of architecture ever seen," are never so arresting as at dusk, when the last rays of sun create a pink hue that languishes into purple—a magnificent transformation locals call the enrosadira. You can certainly enjoy this glow from a distance, but the Dolomites are such an appealing year-round destination precisely because of the many ways to get into the mountains themselves. And once there, in short order your perspective—like the peaks around you—will become a rosy hue.

The Dolomites are strange, rocky pinnacles that jut straight up like chimneys; they are, in fact, the otherworldly pinnacles that Leonardo depicted in the background of his Mona Lisa. In spite of this incredible beauty, the vast mountainous domain of northeastern Italy has remained relatively undeveloped. Below the peaks, rivers meander through valleys dotted with peaceful villages, while pristine lakes are protected by picture-book castles. In the most secluded Dolomite vales, unique cultures have flourished: the Ladin language, an offshoot of Latin still spoken in the Val Gardena and Val di Fassa, owes its unlikely survival to centuries of topographic isolation.

The more accessible parts of Trentino–Alto Adige, on the other hand, have a history of near-constant intermingling of cultures. The region's Adige and Isarco valleys make up the main access route between Italy and Central Europe, and as a result, the language, cuisine, and architecture are a blend of north and south. The province of Trentino is largely Italian-speaking, but Alto Adige is predominantly Germanic: until World War I the area was Austria's Südtirol. As you move north toward the famed Brenner Pass—through the prosperous valley towns of Rovereto, Trento, and Bolzano—the Teutonic influence is increasingly dominant; by the time you reach Bressanone, it's hard to believe you're in Italy at all.