Your tour begins in Columbus Square, where your expert private guide will introduce you to the city’s tenuous relationship with the notorious explorer. In June 2016, the 362 foot of Columbus was unveiled 45 miles west of San Juan on a ceremonial site for the Taíno, a culture nearly driven to extinction by Columbus’s exploits. Learn why islanders are wary of Columbus’s history on their island, and why they attribute centuries of disasters to his name, which they dare not utter in completion.

See Castillo San Cristobal (external only), which was meant to protect the city from attacks by land, and remains haunted by one of the island’s tragic love stories, reminiscent of Shakespeare’s Romeo & Juliet. Other tales include the disappearance of a Spanish soldier whose clothes and gun remained in the remote sentry box; to this day, numerous sightings of the lovers and the soldier are still being reported.

Your private ghost tour of San Juan is 2.5 hours and is all done on foot.