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Lock yourself away on Italy's prison islands, by Tristan Rutherford

Boat International, July 2018


Location: Marooned west of Sicily, a day sail from Tunisia

A volcanic blast gifted Favignana its unlikely history. The 20km² island is covered with calcarenite tuff stone that can be cut like building blocks. The savvy Romans quarried entire swimming pools for themselves, complete with changing rooms and seawater pumps. Their ladies-only bathing area, Bagno delle Donne, survives on the isle’s eastern tip.

Tuff stone also formed the foundations for the Saracen fort of Santa Caterina on Favignana’s volcanic peak. Arabs, then Norman, then Aragonese rulers declared the island’s precipitous interior the perfect spot for a high security prison. Whether the convicts deserved the azure blue views east to Marsala, or west to even more isolated Marettimo, is another matter.

“To Italians Favignana is known as ‘the big butterfly’,” says Y.CO. Yacht Manager Valeria Sangalli. “The dramatic coastline around its two ‘wings’ makes it a great yachting destination.” Any number of irresistible grottos edges the 32km-long shore, including Grotta dei Sospiri, the cave of sighs, which moans in the breeze as you paddle inside. There’s sea life aplenty. Indeed the yearly Bluefin run funnels from Tunisia up through the surrounding Aegadian Islands. Local cuisine revolves around grated bottarga roe and preserved tuna belly. For island exploration Y.CO recommend the 24.9m sloop Ptarmigan (€42,500 per week,, a 2012 Nautor's Swan with hammocks and a home cinema built in.

“In 1874 the powerful Florio family purchased the island and its lucrative fishing rights,” continues Sangalli. The resulting boom called for more tuff rock buildings. One such quarry near the Villa Margherita, which was dug from the 8th century up to the 1960s, has been replanted with island fauna. These Star Wars caves now form the Giardino dell’Impossibile, a rainbow display of oleanders and pomegranates that dazzle against the soft white rock.

Alas, the crumbly tuff blocks have served Favignana’s last surviving penitentiary less well. In 2017 three prisoners cut through the prison bars then lowered themselves free using knotted bed sheets. The trio tried to steal a boat but were tracked down by their wet footprints and reincarcerated the same day. Escaping from paradise is never easy.



Location: A Lost World that’s only welcomed bikinis for two decades

Quite simply, the Italian state is the proprietor of paradise. It owns a 52km² island of virgin Mediterranean fauna, plus a surrounding seabed so kaleidoscopic it’s like an aquarium. The entire scene – located off of the northwestern tip of Sardinian – is a UNESCO-protected National Park. Shockingly, until 1997 it was the preserve of Italy’s most dangerous criminals. These included the Brigado Rosse, Anonima Sarda and Corleone family capo dei capi Totò Riina. Now the island has a census population of just one.

Asinara National Park director Pietro Paolo Congiatu says the biggest attraction is “the great biodiversity in the land and sea”. Wind and waves have carved the coastline into an Italian Cornwall, with rounded rocks, sea kale and flowering gorse. Grab a paddleboard and spot peregrine falcons and striped dolphins.

Congiatu recommends an island tour. “You can ride to the crumbling prison on an electric buggy. And see the turtle centre, wild horses and horned mouflon sheep.” To preserve nature, visitors may swim from just three of the island’s countless beaches. But that’s three more than when inmates kept Asinara off-limits to visitors over the past two centuries.



Location: A paradise prison lost in a sea of Vermentino

The Tuscan Archipelago, midway between Forte dei Marmi and Porto Cervo, is a yachtsman's best friend. Excepting the chain’s tiniest island, Gorgona, which looms like the Rock of Alcatraz replete with Pisan watchtowers and crenulated prison walls. However, the island regime is an enlightened one. When Italy was reunified in 1861 the Kingdom created an experimental agricultural penal colony. Here it was hoped that pine scents and topaz seas would soothe inmates into submission.

“In 2012 we received an email from the prison,” explains Luisa Calvo, spokesperson for Marchesi Frescobaldi (, one of Italy’s leading wine producers. “They asked if we could help them manage a one hectare vineyard.” The 30th-generation president of the group, Lamberto Frescobaldi, sailed 90 minutes from Livorno to find out more.


Frescobaldi discovered a 2km² island carpeted 90% by forest, its indigenous fauna managed by the Tuscan Archipelago National Park HQ on nearby Elba. The remainder was splashed with Vermentino and Ansonica, the latter a tough Sicilian vine that acclimatised to Gorgona’s searing summers, which start 20 days earlier than on the mainland. A partnership was toasted deep in the Tyrrhenian Sea.

“Marquis Frescobaldi knew he could help prisoners to learn a new role to assist them on release,” concludes Calvo. Italy’s toughest prisoners (the 79 inmates stationed include drug traffickers and armed robbers) learn organic farming techniques plus the value of hard work. The rate of reoffending is just 20%, compared with 80% in Italy’s overcrowded mainland prisons. In return Marchesi Frescobaldi produce 3,700 bottles of rich, flinty white, with a red already in production.

As just 47 staff manage the penitentiary, prison breaks are a genuine concern. Unless your captain has written permission from the Italian Ministry of Justice, private yachts may only enter the 500m exclusion zone in an emergency. Hiking trips can be arranged by organised tour but divers will kick their flippers in despair. The surrounding seas have literally never seen a scuba or snorkel.


Tremiti Islands

Location: Swim east and it’s next stop Vis

The Tremiti Islands stand out as the nation’s most bizarre. The furthest of the five is midway to Croatia. Public access is via €30 chopper. And they contain more wreck dives than any other Italian archipelago, including an Ottoman galley, one of Garibaldi’s transport ships and a sunken statue of Italian saint Padre Pio in 10m of crystalline sea. As the islands reside in a Marine Park fishing is banned. Topaz shallows are stocked with seahorses and snapper. Dive deeper for octopus, lobster, cuttlefish and grouper.

Benito Mussolini, never the sharpest knife in the drawer, utilised the islands as a penal colony in the 1930s. Camper and Nicholsons’ Yacht Sales Broker Marco Fodale takes up the story: “The fascist regime exiled those it thought to be gay, lesbian or transgender activists. In 1938 men believed to be homosexuals were consigned to the main island of San Domino.” However, Mussolini unwittingly created the only place in Italy where it was permissible to be openly gay. Labour on the 2km² island was tough. But the local cucina tremitesi cuisine, which has revolved around lobster, lemons, olives, figs and snails since the Bronze Age, eased their existence.

Fodale warns that San Domino’s 10km coastline has no moorings, only bucolic anchorages beset by maquis breeze. An Italian-built charter like 36m Metsuyan IV (€98,000 per week, has the zero speed stabilisers and dive platforms necessary for such a tour.



Location: 50km (and five hundred years) beyond Ischia

“Even though Ventotene is midway between Ischia and Ponza it was discovered the Romans,” says Tonino Cacace, bon vivant and entrepreneur behind the Capri Palace Hotel ( As the civilised Romans exiled miscreants as opposed to murdering them, “Emperor Augustus banished his daughter there, and Tiberius his granddaughter.” The ever-charming Nero ditched his wife Claudia on the 1.5km² island too. Due to a dearth of water and lack of harbour, “Ventotene remained uninhabited for ages,” explains Cacace. “Even many Italians don’t know about it.”

Perhaps that’s because Ventotene replicated its role as a prison for subversive forces in the 20th century. Exiles including Italy’s future president, Sandro Pertini, were also incarcerated in the crumbling prison, which closed in 1965. Nearby, the main square of Piazza Castello has an unhurried rhythm that revolves around sipping macchiato coffees and reading La Repubblica. The only effort expended is to make one’s own wine or catch a pile of fish.

Indeed, Ventotene’s diving is superb. In 2009 archaeologists found five preserved galleys on the seabed with intact cargos of wine, olive oil and garum, an ancient Roman fish source.


Read more Mediterranean island superyacht stories from award-winning writers Tristan and Kathryn. 

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