Outpost City Guide: Capri

A starter course to one of Italys worst kept secrets

In big part thanks to the generosity of a friend who has been going to Capri for close to 15 years, I’ve been fortunate enough to spend time on the island every summer for the past five years.

The first time I went, I stayed for just two days (one night). I got hypnotized by a magician, saw a beach or two, and left thinking, eh, onto the next one.

Man, was I wrong.

Yes, Capri is bougie. But it’s also, objectively, one of the prettiest places in the world. Dramatic cliffs, impossibly blue water, beautiful Italian women—it has it all.

So here’s my best effort at summarizing my favorite places on the island.

Travel

There are two ways to get to Capri: fly into Rome or Naples.