I won’t do Capri as a race. I have no interest in the 6:00 AM scramble for the ferry or the frantic efficacy of the day-trip. To go to Capri is to embrace the overdose—the cliché, the excess, and the unapologetic pursuit of the Good Life.
If you have been several times and have no “musts,” the arrogance of a day trip is acceptable—just to walk the most beautiful path in the world, buy a bottle of scent, have a cone of Capri lemon gelato and leave. But for the rest, the strategically lazy, the island is best handled with a posh collector’s mind. You are here for the once-in-a-lifetime view, the absurd shopping, and the unmistakable silhouette of limestone against an impossible blue.
The Altitude: Anacapri
There are two villages here, and if you are only here for a day, do not try to pack them together. Choose your side. If you prefer space to roam and thinner crowds, go to Anacapri.
It is the island’s higher, quieter attic. At the port, bypass the lines and take a convertible taxi up the cliffside—a road that feels like a dare. Anacapri is where the pulse slows. Take the chairlift to Monte Solaro. It is a single-seat throne that carries you over gardens and silence for thirteen minutes until the Tyrrhenian Sea opens up at the summit. No hiking; just an aerial view of the world. Then, wander through Villa San Michele—the postcard cliché that truly deserves its fame.
The Theater: Capri Town
I, however, go to Capri Town.
The Piazzetta is exactly what the postacrds ask her to be: small, bright, amazing and loud. I’ve come to peace with the theatrics. I walk the polished length of Via Camerelle, letting the scent of fresh waffle cones from Buonocore pull me toward the gardens. I stop at Carthusia to sniff eternal scents—wild herbs combined with lemon in dozens of variations—then move to the Gardens of Augustus to just be part of a poem. If Via Krupp is open, you can follow its unbelievable zigzag down; a piece of beautiful, unnecessary engineering that serves as a reminder of the lengths of a tycoon’s indulgence.
The Best of Capri: Pizzolungo
But there is a point where the only Capri worth dying for begins.
Most people have never heard of the Pizzolungo trail. Of those who have, many avoid it because they fear the seven hundred stone steps. They aren’t wrong—the full loop is a sweat, and for me, sweat is against the purpose.
I give you the lazy hack: the Tragara Out-and-Back.
Walk the flat, flowered stretch of Via Tragara until you hit the Belvedere. From there, the Pizzolungo path snakes along the cliff. Walk twenty minutes into the pine-scented silence, catch a glimpse of the blood-red Villa Malaparte perched on its lonely spur, and then simply turn around. You get to almost touch the Faraglioni, you keep the cliffside silence as a sample of paradise, but you avoid the staircase that tires everyone else.
The Abyss: The Gozzo
I don’t come to Capri for the highest point; I go for the lowest.
Seen from the water, the island feels voluptuous and completely naked. Take the boat for a tour, ideally a wooden gozzo when the sun is low. Looking up, Capri is a vertical, jagged piece of limestone suspended over an abyss of deep blue. From here, the villas aren’t just houses; they are acts of romantic insanity.
The Shift: Glamour
You have to spend the night to say you have truly been to Capri.
In the evening, after the last hydrofoil leaves, the island doesn’t become empty—it becomes glamour. When the yachts drop anchor and the streets thin out, the evening parade of dress jackets and dolce vita replaces the crocs and the backpacks. The frenzy for the masses ends, and a private party begins.
The treasure
The Pizzolungo Trail.
The Intel
The Lazy Hacks for hiking to see Arco Naturale and the Faraglioni:
- The Tragara Side: Flat walk from the luxury shops to the Faraglioni view. Turn back at Villa Malaparte to avoid the 700 steps that take you along the Pizzolungo to Arco Naturale.
- The Matermania Side: Direct 20-minute walk from the town center to the Arco Naturale. A few steep stairs at the end, but no heart popping climbing.
- The Visit: Stay overnight. Give into the excess; expect it to be expensive.
- The Scent: Lemon ice cream from Buonocore and Carthusia herbs.
- The Tale of Two Villages: Anacapri for peace, Villa San Michele, and the Monte Solaro chairlift. Capri Town for luxury, the Augustus gardens, Pizzolungo and the visceral cliffs.
