It has changed names half a dozen times: Isle of Pines for the colonists, Treasure Island in the imagination of sailors, Isla de la Juventud (Isle of Youth) since 1978. Set about a hundred kilometres south of the main island, across the Gulf of Batabanó, Cuba's largest dependency cultivates an identity all its own, built on marble hills, pirate tales, and seabeds ranked among the richest in the Caribbean.

Nueva Gerona, an Unpretentious Capital

The small capital, founded in 1830 at the foot of the Sierra de las Casas hills, isn't trying to rival the colonial cities of the north. The appeal here is atmosphere: the main street lined with colonnaded houses, the steady flow of bicycles and vintage motorcycles, the small local history museum, and the ice cream shops where families line up on Sundays. Near the shore, the old ferry El Pinero, beached right in the middle of the street like a monument, recalls the days when this single steamship was the archipelago's only link to the rest of the country; it was aboard this very ship that Fidel Castro returned to the mainland after his release in 1955. The limestone hills framing the town, long quarried for their marble, form an almost Asian-looking backdrop in the morning light. Mangoes and grapefruits from the nearby orchards, once a point of local agricultural pride, still fill the market stalls.

Presidio Modelo, a Memory in Concrete

Five kilometres to the east, four gigantic concrete cylinders pierced with hundreds of windows rise among the palm trees: the Presidio Modelo, a panopticon-style penitentiary built in the 1920s on the model of a prison in Illinois. It was here that Fidel Castro and his companions were imprisoned after the assault on the Moncada Barracks in 1953. The wing they occupied can be visited; the empty rotundas, where the wind moves freely between the tiers of cells, leave an impression no history book could give. The silence of the place speaks for itself.

Punta Francés, a Diver's Rendezvous

The territory's southwestern tip, protected as a national marine park, justifies on its own the ships' visits: more than fifty dive sites line a spectacular drop-off, among caves, tunnels, wrecks, and coral gardens. The El Colony international dive centre has served these waters for decades. Non-divers aren't left out either: Punta Francés Beach, a long curve of pale sand backed by clear water, welcomes passengers brought ashore by shuttle for a day of swimming and snorkelling over the coral heads. No dock, no kiosk: just a few palapas, the shade of sea grape trees, and the lapping of waves as the only soundtrack.

From Pirates to Pre-Columbian Petroglyphs

French corsairs, English buccaneers, and smugglers flying every flag once frequented these waters, and popular tradition is quick to link the island to Stevenson's novel Treasure Island. More tangible are the caves of Punta del Este, at the southeastern tip, which preserve rock paintings attributed to the pre-Columbian peoples of the Caribbean, a set of red and black concentric circles that archaeologists consider among the most significant in the insular region. Access depends on the excursions offered and on track conditions; check on board before planning your day, since the southern military zone can only be entered with authorization.

A Stop You Leave Reluctantly

Few passengers could point to Isla de la Juventud on a map before docking there; all remember it afterward. Between the penitentiary's rotundas, the depths of Punta Francés, and the provincial calm of Nueva Gerona, the stop paints a portrait of Cuba far removed from the usual itineraries. The ship sets course north again, and it becomes clear why so many names have come and gone: each one captured only a single facet of this many-sided land.