A ferry ride across the Gulf of Naples will take you from Positano to the idyllic island of Capri which has beguiled visitors for millennia. The Roman Emperor Augustus made the island his vacation home, while his successor Tiberius decided to live here year-round, ruling Rome from his collection of villas while contributing to Capri’s reputation as a haven for hedonism. Today Capri maintains its status as a decidedly upscale libertine playground. While there you can visit the ruins of Villa Jovis, in the northeast of the island. Judy will arrange for a guide who will transport you back to day of Tiberius as you explore one of his 12 former enclaves. On the west coast of the island, a private boat tour will take you to the legendary Blue Grotto, a stunning sea cave with electric blue water.