Built in the late 19th century to ferry military supplies through the rugged Caucasian highlands, the name of this famed highway belies the rich history and beauty of the region it traverses. Setting out this morning, you’ll visit Ananuri, an impressive medieval fortress with far-reaching views of the Caucasus and turquoise-hued Aragvi River. Continue past alpine meadows, ancient churches, and medieval forts in varying states of disrepair. Then ascend through the Jvari Pass at 7,800 feet to Kazbegi, near the Russian border, and check in to the stylish Rooms Hotel. Meals B+L+D