YHA Fremantle Prison (Perth, Australia)

When the first convict transports arrived in Western Australia aboard the Scindian in 1850, they were forced into hard labour to build their own prison. Housing nearly 10,000 men by 1868, Fremantle Prison grew into the largest convict-constructed building in the southern hemisphere. It was used as a maximum-security prison until 1991, when it was decommissioned, repurposed, and converted into one of 11 museums that make up the Australian Convict Sites, collectively a UNESCO World Heritage Site. Daily tours focus on Fremantle’s convict past, modern penal history, the transport era, and a torchlit visit to water tunnels dug beneath. Visitors can also tour the gloomy gallows and learn about the 1988 prison riot that ultimately led to the prison’s closure in 1991. The adjacent women’s barracks have since been converted into a backpacker hostel, with dorms and private rooms, free Wi-Fi, a lounge, a communal kitchen, and other amenities. Since the small, two-bunk cells are a little too crowded for families, we did our time in the adjacent colonial cottages, built by prisoners for the wardens. It’s an ideal spot to lock in a little shut-eye before exploring the trendy neighbourhood of Fremantle.

Malmaison Oxford (Oxford, England)

“Better than your average prison,” jokes the website of this boutique hotel in the heart of Oxford. It also promises a sentence of “comfort and contemporary charm.” With an imposing stone building dating back to William the Conqueror in 1107 (and the actual gaol to the 12th century), the prison housed thieves, political prisoners, and debtors shackled by their debts. It was decommissioned in 1996, refurbished and reopened in 2005 as a 95-bedroom hotel with duplex and circular suites. Located within the grounds of Oxford Castle, the site offers visitors access through an imposing gate and includes three zones: the original main building, a modern extension known as the House of Corrections, and cells converted into premium hotel rooms. Narrow corridors still feel like cellblocks, but the ambiance is warm and classy, with staff offering glasses of prosecco instead of cell beatings.

With so much history to work with, designers have gone to town with the metal galleries, glass walkways, prison-themed cabinets, a mood-lit central atrium, and cells named after notorious inmates and wardens. It’s been more than 70 years since the jail hosted an execution, but you don’t have to worry about sleeping with that psychic energy, as the hanging cell is in today’s staff area. There’s a courtyard, restaurant, bar and adjacent castle to explore on-site, and you’re just a five-minute walk to Oxford’s town centre. The old prison has also been used as a location for classic British TV crime shows like The Bill and Inspector Morse.

Four Seasons Hotel Istanbul (Istanbul, Türkiye)

Istanbul’s Sultanahmet district is one of my favourite places on the planet. Sitting on benches between the Blue Mosque and the Hagia Sophia, expect goosebumps at sunset when the minarets light up, the Call to Prayer echoes, and history sneaks up and whacks you over the head. The Four Seasons nearby is regarded as one of the world’s best urban hotels, and while you might think it was an opulent palace for the sultans, the origins of the manicured lawns and marble floors were actually a prison. It was constructed in 1918 to be the first jail in the capital of the Ottoman Empire, incarcerating the most heinous prisoners (women and children included) as they awaited trial in the courthouse next door.

During its transformation from a prison to a luxury hotel and spa, some of the original marble and stone were reused to add a touch of history to the jasmine- and bougainvillea-lined courtyards. You can also spot architectural clues in the long hallways, arched windows, and quadrangle layout typical of the era’s penal facilities. The cells have long made way for refined rooms with handwoven carpets, soaker tubs, and views of the gardens and mosques. The Grand Bazaar, Topkapi Palace, and the Bosphorus are just a few minutes away, too.