Remoteness from other parts of the world, frigid or fierce currents, and the presence of sharks are some of the obstacles that make an escape from island prisons difficult, if not impossible. However, these same conditions make such locations ideal for prisons, especially those set aside for incarcerating the worst among violent, predatory killers, rapists, and robbers, although some such sites are also used to incarcerate political prisoners whose only crimes may be their inconvenient ideological positions.
In most cases, the governments that chose the locations on this list were correct: the islands were ideal places to establish penal institutions. Except for a couple of these island prisons, escape was rare. In almost all other instances, only a handful of prisoners, at most, and, usually, only one or two, were able to successfully flee from the often stark, vile, and dangerous prisons to which they had been consigned.
Here are the stories of the few who risked everything for a chance at freedom, however ill-deserved, in some cases, their liberty might have been.
Related: Top 10 Women Who Managed To Escape Prison
10 Roy G. Gardner
As Sean Roberts points out in “Who’s Who of McNeil Island Prisoners,” the U. S. federal penitentiary on McNeil Island was home to many of the most dangerous criminals in the country. Its inmates included “bandits, sociopaths, killers, [and] con artists.” Among its population were such infamous figures as Robert Stroud (1890-1963), “The Birdman of Alcatraz,” as he was later known, who occupied a cell from 1909-1912; Charles Manson (1934-2017), a guest of the feds at the pen from 1961-1966; and Alvin (“Old Creepy”) Karpas (1907-1979), who resided there from 1962-1969).
For those who were familiar with the local geography, escape from the 17.27-square-kilometer (6.63-square-mile) island off the coast of Tacoma, Washington, might have been difficult, but it was not impossible. The bigger problem was crossing Puget Sound. Although the island lies from east to west across the Sound and is about three miles from Steilacoom, its western side is only 700 yards away from Key Peninsula, where some of the intervening water is shallow enough to wade. Over the years, as many as 100 prisoners escaped from the prison itself or from work details, but only about two dozen of them were able to cross the Sound. The others perished, presumably by drowning.
One of a dying breed, Roy Gardner (1884-1940) was a train robber. According to a Sky History article, he is most remembered for his escape from McNeil Island, considered “the most secure prison in America at the time.” His getaway involved the unwitting participation of two dupes, also inmates, whom he intended to serve as “decoys.” He convinced them that they could pull off the escape safely by fleeing together. There was safety in numbers, he suggested. There was not: guards fired upon all three of them. Gardner alone got away at the cost of “a minor” leg wound.
Despite the injury, he “swam to a neighboring island,” a free man. Assigned to the Most Wanted List, he returned to his old ways, attempting to rob another train several months later. Recaptured, he received another 25-year prison sentence. Following additional escape attempts at two other prisons, he was finally sent to Alcatraz in 1934, where he remained, planning another escape until he was paroled in 1936, only to commit suicide two years later, after publishing his autobiography.
9 Clement Duval and Henri Charrière
By order of Emperor Napoleon III (1808-1873), the prison nicknamed Devil’s Island was established in 1852. From the beginning, the small island, one of a cluster near the coast of French Guiana, was the home away from home of such violent offenders as murderers and rapists, as well as political prisoners.
According to Australian news reporter Kate Schneider, life was difficult for prisoners, who, chained by day and shackled to iron bars by night, worked from sunup to sundown, some constructing buildings—their own claustrophobic 1.8-x-2-meter-wide (6-x-6.5 foot) cells included. Rations were so meager that “some became walking skeletons,” Schneider observes. To avoid paperwork, guards often allowed fights among prisoners to go unpunished. In the event that a fight was fatal, the deceased would be dumped into the ocean, and a bell would be rung to summon sharks.
Rough, shark-infested seas made escape difficult; the few who managed to reach the mainland had to contend with the dangers of the jungle. “It was really a living hell, especially when you realize that out of 70,000 men, three-quarters died here from disease, from hunger, from mistreatment,” prison guide Hermann Clarke said.
There were only two successful escapes, one by Clement Duval (1850-1935), the other by Henri Charrière (1906-1973) and his companion Sylvain. Duval, who escaped in 1901, lived out his life in sanctuary in the United States. He tells the story of his experience in his posthumously published Outrage: An Anarchist Memoir of the Penal Colony (2012). The escape of Henri Charrière and Sylvain is recounted in Henri Charrière’s loosely autobiographical, apparently partly fictional, book Papillon (1969).
8 John Anglin, Clarence Anglin, and Frank Morris
The FBI itself details the escapes of three inmates from notorious Alcatraz Island in the San Francisco Bay. According to the results of their investigation of the evidence and information from a fourth prisoner, Allen West (1929-1978), who was supposed to join them, John Anglin (1930-?), his brother Clarence (1931-?), and Frank Morris (1926-?) conceived and executed “an ingenious” escape plan over a period of nearly a month (June 12-July 11, 1962).
They sculpted dummy heads, painted to match their complexions, and equipped them with human hair, positioning them on their cots so that they appeared to be the heads of the men themselves, asleep. Guards were initially fooled by the ruse, but upon discovering the escape, the prison was locked down, and an investigation began.
Investigators determined that, after drilling holes around the frame of the air vents at the backs of their cells, they removed these sections of their cell walls and entered the unguarded service hallway that ran behind the cells. The corridor gave them access to the roof of their cell block, which was inside the prison building. On the rooftop, they established a “secret workshop,” the FBI learned.
The escapees fashioned “crude tools” from available items, converting a musical instrument into an inflation device and creating a “periscope” through which to keep an eye on the guards while they worked. Other evidence was discovered in the ocean, including rubber-sealed letters associated with the escapees, pieces of wood resembling paddles, and a makeshift life vest. The life vest, like the men’s 4- x-14-foot rubber raft, had been made from fifty raincoats the men had acquired, probably through loans.
On the day of the escape, the men pried up the ventilator atop the ventilation shaft, entered the rooftop, climbed down the prison bakery’s smokestack, crossed the grounds, climbed a fence, and launched their raft from the island’s northeast shore, planning to cross Raccoon Strait and enter Marin County.
To this day, no one knows the fate of the escapees. Did they reach the mainland? If so, where have they been since July 11, 1962? It would have been difficult to cross the Bay because of the strong ocean current. West said that the men planned to steal clothing and a car once they made it to the mainland, but no reports of such crimes were ever received at the time of the escape. The escapees’ families did not earn enough money to provide meaningful financial assistance. The FBI has never found any “credible evidence…to suggest the men [are] still alive.”
Although the Bureau closed the case on December 13, 1979, in doing so, they closed the books on a mystery. No one knows what became of the men who escaped the maximum-security prison on Alcatraz Island. Though plenty of rumors of their whereabouts and lives after the escape pop up from time to time.
7 David Stuurman
A leader of the resistance to British colonialism in South Africa during the late 1700s and early 1800s, David Stuurman (1773-1830) and the Khoi and Xhosa people he led were regarded by the British as threats to be subjugated. According to cultural activist Stephen Langtry, Stuurman “was arrested and charged [with] resisting colonial rule as well as opposing the conscription of the Khoi into militias that were created to defend the colony and to attack the San and Xhosa” peoples.
As a prisoner of the British, Stuurman was incarcerated on Robben Island, off the coast of Cape Town, South Africa, from which he escaped not once but twice. In his first escape, he stole one of the whaling boats at anchor in the harbor, taking refuge among the Xhosa.
After being captured again, Stuurman was sentenced to hard labor on Robben Island. However, he escaped again, this time using a boat, which capsized. Although he survived, he was captured yet again and sentenced, once more, to the same island prison, where he was chained to a wall, awaiting transport to Australia, where, unable to return home after his release six years later due to a lame right leg, he died. His grave was lost when the cemetery where his remains were buried was “redeveloped as Sydney’s central railway station.”
6 Matteo Boe
Asinara Island, stretching along the most north-western edge of Sardinia, was home to the bandit Matteo Boe, who lived in one of the cells of the “unlikely looking Italian prison that stands one step away from the blue sea,” as an e-borghi.com article describes the correctional institution’s setting.
The prison’s clay roof tiles; white walls, reflective of bright sunlight; and dark-blue doors and window frames, mimicking the deep color of the cobalt-blue sky, give the prison a pleasant, almost festive, albeit incongruous, appearance. This makes the prison look more like a seaside retreat than a house of correction. The color scheme is repeated inside: the cell doors, like the frames of the small windows above them and the numbers painted on the white walls beside the cells, are the same dark blue as the prison’s exterior walls’ window frames. Only the presence of the padlocks and chains suggest the purpose of the place.
Despite such appearances, the prison’s captives included one-time Cosa Nostra leader Tito Riina, ex-Camorra chief Raffaele Cutolo, and, of course, bandit Matteo Boe. According to the article, the prison was also a “place of refuge for the late judges Giovanni Falcone and Paolo Borsellino, who were put under protection until the start of the maxi trial.”
The only Asinara Island prisoner ever to escape the prison, Matteo Boe, aided by his cellmate, fled the “Italian Alcatraz” by rubber boat. Until Boe’s getaway, the penal institution had been thought to be escape-proof. The maximum-security prison closed in 1998. Now part of the Asinara National Park, it is a favorite spot among visiting tourists.
5 Seventy-Six Escapees
Located on a Pacific archipelago off the Mexican coast is “Mexico’s Tropical Alcatraz.” Despite its nickname, the “escape-proof” Isla Maria Federal Prison Colony has been the scene of no fewer than seventy-six escapes, writes Danielle Ong in her Latin Post article concerning the site. Perhaps the institution’s “violence, disease, forced labor,” and torture, which she mentions, inspired escape.
Prompted by his belief that such a place might spur local development and boost “national pride,” President Jose de la Cruz Porfirio Diaz Mori (1830-1915) decided, in 1877, that an island prison colony the likes of the United States’ Alcatraz should be built. By 1905, the Isla Marias Federal Penal Colony was complete. Six of its many escapees used plastic containers as a flotation device, but they, however, were captured and returned to the tropical Alcatraz.
Those whose escapes were successful were usually aided by bribes to officials and other staff members, including, perhaps, the Reyes Servin brothers, members of a family notorious for kidnapping.
By 2019, President Andres Manuel Lopez Obrador had had enough, citing “expensive maintenance costs as well as the island’s tendency to be hit by violent tropical storms.” He closed Isla Marias but made no mention, apparently, of the “island prison having been prone to escape.”
4 IRA Members and Other Internees
Located near Cork, Ireland, close to the harbor’s entrance, Spike Island was a stop-over point in the shipments, from 1840 to 1880, of convicted prisoners bound for Australia. Beginning in 1921, however, the island prison began to be used to incarcerate prisoners who had been “convicted by courts-martial under the Restoration of Order in Ireland Act,” writes Diarmaid Ferriter, author of the book On the Edge: Ireland’s Off-Shore Islands: A Modern History.
In November 1921, seven prisoners escaped under cover of darkness. The prisoners’ construction of tunnels aided escapes, as did prisoners’ contact with friends on the mainland. This communication was accomplished through an intermediary, “the boy who accompanied the priest saying mass in the internment camp,” according to Patrick Burke, a Waterford IRA volunteer who assisted in the tunnels’ construction.
The tunnels were not always a means of escape, however. During a work detail, Ferriter observes, five prisoners were allowed, under armed guard, to bathe along the seashore. However, they “slipped away through the open door of a stable as the party passed through a farmyard” as the escapees “were shielded by a tall man in front and rear.”
3 Vladimir V. Tchernavin
Vladimir V. Tchernavin (1887-1949), an ichthyologist, wrote I Speak for the Silent Prisoners of the Soviets (1935) after his escape from a prison in the Solovetsky Islands. He had been sentenced for five years after being convicted, in 1931, of “wrecking” by having promoted price increases related to certain “materials and production equipment.” (The charges are vague.)
His account of his incarceration is harrowing, as are the details of the Soviets’ interrogation methods, which included withholding food, sleep deprivation, the withdrawal of privileges, solitary confinement, prolonged questioning sessions, threats of execution, and torture. To put additional pressure on Tchernavin to confess to his alleged crimes, the Soviets also arrested and imprisoned his wife, Tatiana.
The last few pages of his book describe Tchernavin’s escape from the prison island. Given the opportunity to lecture about and head several projects related to fishing at various locations throughout the far-north, frigid District of Murmansk Oblast, Russia, Tchernavin made sure that one such site would be near the spot at which he planned to escape.
When he reached this site, his wife Tatiana, who had been released from prison, and their son were waiting for him. The family set out, Tchernavin wrote, “in a leaky row-boat, patched by [his] own hands.” Then, with neither compass nor map, they hiked “over wild mountains, through forests and swamps, to Finland and freedom.” Tatiana also chronicles their escape, in greater detail, in her 1934 book Escape from the Soviets.
2 Billy Hayes
In 1970, writer-actor-director Billy Hayes was arrested for trying to smuggle a couple of kilos of hashish out of Turkey. For his trouble, Hayes was sentenced to life in prison, but after serving five years, he escaped from the island prison in which he was incarcerated. “I got myself into jail,” Hayes summarized his ordeal, “and I got myself back out.”
A Bronx-born Marquette University dropout, he turned drug smuggler, three times illegally importing two kilos of Middle Eastern hashish he had “concealed in a fake leg cast,” according to David J. Krajicek’s newspaper article on the subject. The fourth attempt landed Hayes in a cell in Turkey’s Sagmalcilar Prison, in Istanbul, during a series of coups and insurgencies. At the request of his parents and the media, the U. S. government was working diplomatically, behind the scenes, to secure Hayes’s release when he decided to escape.
A bribe bought him a transfer from Sagmalcilar to Imrali Prison Island in the Sea of Marmara. There, prisoners “were allowed some freedom,” Krajicek says, “since only a fool would attempt a swimming escape from Turkey’s Alcatraz.”
When a storm prevented crews from using boats to deliver supplies, Hayes, a fit, expert swimmer, used one of the rowboats that delivery crews employed to take supplies to the boats, which they then delivered to their customers. He then rowed his way to a group of “supply vessels” anchored in the sea.
Once ashore, he posed as a Turk, took a bus west 100 miles to the Maritsa River separating Turkey from Greece, swam the river, and turned himself in to officials at the U. S. consulate in Greece. Oliver Stone’s 1978 movie Midnight Express is very loosely based on Hayes’s exploits.
1 Napoleon Bonaparte
The site of Napoleon Bonaparte’s incarceration fit his stature: the whole island of Elba was the exiled emperor’s “prison.” After being defeated and deposed in 1813 at the Battle of Leipzig, Napoleon (1769-1821) signed the Treaty of Fontainebleau, forking over his “royal property,” History writer Erin Blakemore notes, as well as his own and his descendants’ right to rule.
The same treaty allowed him to retain his title of emperor and to select an island to rule. He chose Elba, which had been part of France until it was reclassified as a principality to be ruled by Napoleon. His mistress, Marie Walewska, a Polish countess, joined him in his new realm. They made a villa built by the Medicis overlooking the harbor their main home, reserving for themselves a second residence as their summer house. Between lavish parties, the Emperor of Elba built an army while plotting his escape from the island.
From continued communications with loyal friends in France and with visitors, Napoleon learned that his own followers intended to rebel against King Louis XVIII, just as those who did not support him planned to remove Napoleon to the more-distant island of St. Helena. The emperor feared that he might not be remembered after his death, but his mother, who was now one of his Elba subjects, encouraged him to “fulfill [his] destiny.”
On February 26, 1815, Napoleon sailed back to France amid a flotilla of ships carrying 1,150 loyal subjects. His “bold prison break worked,” Blakemore declares, as he “arrived in Paris a hero.” Napoleon ruled France again—for 100 days, at any rate, before his decisive defeat at the Battle of Waterloo and his exile to St. Helena.