The island, dubbed "The Silent Isle" or "Donkey Isle" due to the animals that inhabit it, used to be a quarantine hell where criminals, Mafiosi and people sick with leprosy were locked up and confined up until a few decades ago.
The place has been restyled into a cozy hotel where windowless rooms still feature original wooden cell doors shut by lockers and identified with big painted numbers.
Breakfast and meals are in military barracks where guards and inmates used to hangout. To recreate the ambience the jail's brutal former glory, the menu features the dish "porceddu sardu", a baby piglet spiked on a bonfire and roasted in its own blood to make the coating crunchy.
The abandoned prison village still features the old drugstore, whitewashed chapel, infirmary, benches and barber shop.
No cars are allowed on Asinara. There are just bikes, a little train to tour the island and lots of dusty trekking paths to stretch your legs. Beach bars rise close to rusty bunkers. Prepare to bump into goats, wild boars, horses and albino stout donkeys that freely roam the hills and beaches.
But if you're looking for the real thing, where murderers on probation cook meals and rapists serve evening cocktails out on the porch, head to operating prison isle Pianosa, off the coast of Tuscany.
The island's only hotel restaurant is run by inmates, so you actually get to sleep right next door to them, greeting each other with a nice "ciao" and even bathing in the same water.
During the day, convicts leisurely stroll across the tiny village, walking horses and helping out at the hotel. They've turned into holiday planners, taking guests out snorkelling, kayaking, on butterfly hunts and on horse carriage tours.
It's part of their rehab mission so don't freak out: these are the "good" baddies that dream of a fresh start and would never hurt a fly. When I first spoke to Franco the cook, serving a 25-year sentence for murder, I had goose bumps but loved his spaghetti with sea urchins.
Italian prisons are overcrowded and if you're the wannabe convict longing for a sojourn behind bars, there's a long waiting list, so book in advance. Only a limited number of visitors are allowed each year on Pianosa.
And it's love at first sight. Tourists come back regularly and many choose this slice of paradise to tie the knot. They feel part of a big "convict family".
"At the beginning, I was constantly watching over my shoulder. You never know!" says Roberto Giuliano, a frequent guest.
"But then I made friends with the prisoners and at night we stayed out watching falling stars and the famous barracuda dance."
Don't worry, the barracuda dance isn't a murderous game: it's just a bunch of barracudas that get together at dusk and swirl around in front of the beach, making the water glitter. And how about the thrill of actually going to jail for dinner or a quick business lunch?
There are now new restaurants and bistros inside prisons where inmates prepare gourmet recipes and create sublime pastries.
Milan's main jail has recently opened a restaurant where eight prisoners cook and serve tables. You'll meet convicts of all imaginable crimes, except Mafiosi — they're considered the worst breed and don't get to rehabilitate.
The decor reflects the setting. The entrance is an iron door with a large rectangular peephole that recalls super-maximum security cells. There are screens through which prisoners are allowed to talk to parents and friends.
Metal cages and bars hold wine and champagne bottles and there are wall posters of famous theme movies like Papillon and Escape from Alcatraz. Guests get to eat on paper placemats with pictures of popular prisons such as the Tower of London, the Spielberg Castle and Sicily's nasty Poggioreale, one of Italy's most hellish jails.
There's no need to pass under a metal detector to get in.
"My friends took me there for a surprise dinner once, when I discovered I was in jail I was shocked but curious," guest Maria Alba says.
"It's very provocative. I've come back three times. This place rocks, the food and waiters are great."
It's haute cuisine. Specialty dishes include risotto with ginger and rum-sprinkled scallops; sea bream with pink pepper, honey and orange; and mousse with meringues and persimmon for dessert.
These same "criminal chefs" also take part in catering events and celebrations at lavish Baroque palazzos, historical villas and sleek skyscrapers across town, so chances are you'll run into a few in town.
Padua's jail is heaven for the sweet-tooth, where a sophisticated pastry lab has been set-up under the label "Giotto's Cakes" and stages gourmet events.
Inmates who work here have gone through bitter stories of violence but now embrace sugary delight. They show off their artistry in food exhibitions across Italy. Their pies and cookies are even sold to the Vatican to satisfy the pope's tastebuds. They make artisan versions of Italy's iconic Christmas cake Panettone, nougat torrone, grissini bread sticks, Colomba dove-shaped Easter bread, ice-cream and special "penance" beer biscuits created with monks when the relics of St Anthony, protectors of prisoners, were taken for a ride inside the prison walls to bless the inmates.
Greek hero Odysseus' words are written at the entrance of the pastry shop: "You were not made to live like brutes, but to follow virtue and knowledge". It's a purification mission through sugar, and they also get paid for it.
"We've won several prizes and recognition at pastry fairs, so I guess that at the end we have done something good. It's important that people don't see us like monsters", says Elvin, who is in charge of controlling the doughs' leavening.
His buddy-behind-bars Giovanni knows what he'll do once he's free: he'll become a pastry chef.
"I've learnt a job here, it has saved me from rotting in jail and recovered my dignity," he says. Reoffending rates across Italy are higher than 80 per cent, but in Padua's prison, it's barely 2 per cent.
In Naples, the kingdom of superstition, a bunch of teenage inmates has become famous by making black and red chocolates shaped like bull horns, believed to keep jinx away. In Volterra, criminals perform in Shakespeare's plays.
While women inmates kill time making and selling fashionable clothes that are showcased on fashion weeks' catwalks. In one Milan jail a bunch of young wanna-be-designers have launched a chic atelier to the public, where fashion addicts get to pick bespoke garments.
In an irony of sorts, the ladies design the black and golden robes of many judges and lawyers who, by the way, are all still alive.