From Tiberius to the modern jet-set, Capri has long been a magnet for decadence
Capri today attracts the LGBTQ+ international elite. The island has gay bars and a summer season where sexual orientation matters far less than your access to a yacht. What most contemporary visitors don’t understand is that this represents continuity, not recent invention.
Capri has always been about sexual power and pleasure without apology. That story starts with an emperor who retreated here and never left.
The Island as Political Theater
Tiberius ruled Rome from 14 to 37 CE. In his late sixties, he abandoned the capital entirely and moved to Capri. For the last decade of his life, he governed an empire from an island retreat, communicating through letters and intermediaries. The decision scandalized Rome. An emperor wasn’t supposed to hide. He was supposed to be visible, performing power constantly in public spaces.
Tiberius understood something different: power doesn’t require physical presence if you control narrative and fear absolutely. He used Capri to reorganize governance around himself without the messiness of competing with the Senate in Rome. He also used it to live without pretense.
The historical record from Suetonius is graphic. Tiberius allegedly kept a staff of attractive men and organized elaborate sexual parties in hidden grottos. His antics pre-dated Berlusconi’s bunga bunga parties by many centuries.
Whether every detail is accurate matters less than understanding that Suetonius documented this without suggestion that the sexual practices themselves were the scandal. The scandal was an emperor withdrawing from Rome.
What Grotta Grande Actually Represents
Villa Jovis overlooks the Tyrrhenian Sea from the island’s northeast cliff. The ruins aren’t spectacular in the Instagram sense. They’re fragmentary, positioned dramatically, and deeply revealing about how Tiberius thought about privacy and power. The villa could house hundreds. It was organized around multiple private chambers, viewing platforms, and hidden passages. This was surveillance architecture designed by an emperor.
At the base of the cliff sits Grotta Grande, allegedly accessible through internal passages. The grotto was supposedly where Tiberius organized what Suetonius called his most explicit sexual gatherings. Young swimmers (allegedly recruited and trained) would perform in the water below while Tiberius watched from above. The architectural specificity matters. Whether the detail is historical fact or Suetonius’s invention to discredit a dead emperor, the point is the same: Capri represented a space where an emperor’s sexual desires operated without Roman social constraints.
The Power Structure of Desire
Understanding Tiberius on Capri requires understanding how Roman sexual hierarchy functioned. Sexual penetration wasn’t morally neutral. An elite Roman man penetrating a younger partner (male or female) was exercising power and dominance. The penetrated person, regardless of gender, was taking a submissive role understood as feminizing and degrading. For an emperor, the ability to dominate sexually without consequence was simply another expression of absolute power.
Tiberius’s sexual practices on Capri weren’t hidden because they violated some ancient moral code. They were documented and discussed because an emperor exercising power without restraint threatened the Senate’s pretense of shared governance. His withdrawal from Rome, combined with his absolute control of sexual access and sexual practice on Capri, represented a complete reorganization of power around personal preference rather than public obligation.
The island became an extension of his will. Everything that happened there reflected his desires. No competing interests. No Senate to negotiate with. No pretense of sharing power.
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Walking Villa Jovis Today
You approach through a modern stairway to a wooden platform overlooking the sea. The ruins of the palace sprawl across the hilltop: fragmentary walls, collapsed chambers, the organizational structure visible only if you understand how these spaces functioned together. The positioning is deliberate. Rooms overlook other rooms. Terraces command views across the island and toward mainland Naples. Tiberius could see who arrived, who moved through his villa, who accessed which spaces.
The descent to Grotta Grande requires significant effort. A modern metal stairway descends the cliff face. The grotto itself is simple: natural rock, water access, the kind of space where an emperor could be unseen while observing others. Whether the historical accounts are literal truth, the architecture suggests Tiberius designed spaces specifically for watching and being watched according to his preferences.
Standing inside the grotto, you’re in a space created for sexual power without public accountability. That’s not romantic. It’s revealing about what absolute power actually means.
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Contemporary Capri
There are no gay bars in Capri – it’s a fairly small island – but it’s very gay-friendly. Taverna Anema e Core is Capri’s most famous nightlife spot, a place where live music, spontaneous dancing, and high-octane socializing fill every corner.
Gianluigi Lembo and his band set the tone with a mix of classic Neapolitan songs and international favorites that bring the whole room together. Celebrities such as Beyoncé, Mariah Carey, and Leonardo DiCaprio have all joined in during the night, yet the real charm of Anema e Core is that every guest is encouraged to be part of the experience. It is warm, welcoming, and full of character.
Punta Tragara remains the island’s most exclusive resort, designed by architect Luigi Cosenza in the 1950s. The property sits dramatically on a clifftop with views across the Tyrrhenian Sea. It’s expensive, minimalist, and historically frequented by upwardly mobile travelers.
Caesar Augustus Hotel is one of the most exclusive addresses on the island of Capri. This five-star Relais & Châteaux property combines timeless elegance with sweeping views over the Bay of Naples, Mount Vesuvius, and the Sorrentine Peninsula. Far removed from the crowds of Capri town, it offers a quieter, more refined escape without sacrificing access to the island’s best experiences.
Originally a private villa, the hotel still feels like a grand residence. Each room is individually decorated with handpicked antiques and light Mediterranean tones that reflect the beauty outside. Many rooms feature private terraces that open onto one of the most iconic views in all of Italy. The infinity pool appears to float above the sea, while manicured gardens and shaded pergolas.
Dining at Da Paolino in Capri is as much about atmosphere as it is about the food. Set beneath a canopy of fragrant lemon trees, the restaurant offers one of the most unique and memorable outdoor dining experiences on the island. By day, the scent of citrus floats through the air; by night, the trees are lit by soft lanterns, creating a romantic, almost dreamlike setting that has become hugely popular.
The menu is grounded in traditional Caprese and Neapolitan cuisine, with generous portions and bold, authentic flavors. Guests come for house-made pastas, locally caught seafood, and signature dishes like lemon-scented risotto or grilled swordfish with herbs.
People eat at Da Paolino not just to enjoy good food, but to be part of a Capri tradition. It’s a favorite of both locals and celebrities, yet it remains unpretentious and welcoming. In a place where the experience matters as much as the menu, Da Paolino delivers both effortlessly.
The Historical Through-Line
What Tiberius understood about Capri persists. The island operates according to principles its residents control. It’s geographically removed from mainland Italy’s conservative Catholic politics. It’s expensive enough to maintain an air of exclusive decadence.
Ready to explore Capri? Let us craft a luxury itinerary that connects you with the island’s historic legacy, imperial villas and nightlife, all with five-star service and seamless logistics.
