As we sailed across the Bay of Naples from Sorrento toward Capri, the boat captain pulled me over and pointed to the highest point on the island. "That's where you're going," he said. I had been obsessed with the Monte Solaro Chair Lift, a single-seat, open-air ride to the mountaintop, ever since I learned about it from a fellow traveler. But looking up at the 1,932-foot peak from sea level, it suddenly felt daunting.

Capri has long solidified its reputation as a yacht-filled glamorous getaway, a favorite of celebrities from Audrey Hepburn and Grace Kelly to Kourtney Kardashian and Hugh Jackman, with its dramatic rocky coastline set against transparent blue waters. Though its most famous landmark is, no doubt, the Blue Grotto, the cave with naturally glowing blue waters, its most underrated attraction might just be the unique lift to the top of Monte Solaro.