The big sleep: soft cell for guests

Boston's Charles St Jail was as notorious for its brutality as its infamous inmates. Now it has been reborn as a five-star hotel

It is early Sunday morning and the inmates are stirring. Those who prefer solitary confinement request their breakfast victuals in their cells while others make their way to the slop hall where French pastries and miniature quiches are served. Fitness nuts make for the "exercise area", grabbing complimentary headphones to enjoy music on the treadmills. The bravest are staging break-outs to the city outside while black-uniformed wardens open fire with fusillades of words: "We hope you enjoyed your stay."

Something has happened to the Charles Street Jail in downtown Boston, an imposing cruciform of grey granite and brick that for more than a century and a half served as the city's main slammer, the first point of confinement for assorted crooks and trouble-makers – its drunkards, gangsters, murderers and wife-beaters – while they awaited their fate at trial. Once infamous for its crowded, inhumane conditions, today it is striving for different kind of reputation. Stink has given way to sexy; misery to magnificent luxury.

The resurrection of the Charles Street Jail that sits close to the banks of the Charles River and just below Beacon Hill, Boston's exclusive enclave of handsome townhouses and hidden lanes, as a five-star hotel – it opened just last week and has already taken reservations from the likes of Annette Benning, Deborah Messing and Meg Ryan – is not a unique occurrence in the world. Cities as far apart as Oxford and Istanbul also boast deluxe hostelries in buildings that once were houses of incarceration. Yet the question can be legitimately asked: where are the boundaries of good and bad taste in such conversions?

If you are interested in staying in Boston's old jailhouse, look on the web for the "Liberty Hotel". Your research will reveal that the breakfast which yesterday was so refined – miniature grapes adorned each quiche – is cheekily called "Clink" as is the cocktail bar. Soon to open near the main entrance is another restaurant "Scampo" , Italian for escape, and a second bar, "Alibi". The walls of the latter will be adorned with real mug-shots of American celebrities who have known brushes with the law, including Lindsay Lohan, Frank Sinatra, Nick Nolte and Mel Gibson. The marketing blurb exhorts with attempted whimsy: "Let yourself be captivated".

"I don't think everyone enjoyed being here," Stuart Meyerson the general manager of the Liberty dryly admits over cocktails at the Clink. He was not referring to his guests from the few nights since its opening but to the thousands of benighted Bostonians who knew its walls in its former incarnation. He confirms that in conceiving every detail of the hotel and in pondering how best to market it, the new owners had "to walk a very fine line". He adds: "Clearly, there are some very dark and depressing elements to this building and we have to be careful how we tell its story."

New visitors, for example, almost invariably first inquire about what famous inmates were once locked up in the original facility. It is a question that Meyerson is reluctant to answer. Better he talks about today's glamorous Hollywood guests than about the Boston Strangler who found himself here in the late Sixties or the lamented anarchist duo of Nicola Sacco and Bartolomeo Vanzetti who were held in its cells before their execution eighty years ago last month, widely considered a gross miscarriage of justice that triggered protests and riots in cities in Washington DC, London and Paris. Two new books and a film testify to the continuing interest. "We don't talk about that too much. These are fascinating stories, but to some people it is still very private and personal."

Designed by Boston architect Gridley James Fox Bryant, the Charles Street Jail was adopted as a model for prisons around the world when it was first opened in 1851. It represented a revolution in detention design. Fox Bryant constructed an octagonal central rotunda beneath a 90-foot-high wooden ceiling and cupola that today serves as the hotel's undeniably imposing atrium lobby. Four wings radiated from the central hall like spokes, with parades of cells behind iron-barred doors. It was the first jail in America to afford inmates individual cells and wide landings were used for work and learning trades. Wardens paced walkways encircling the atrium to watch for trouble on each of the wings.

Glorious, the building's history is not, however. An uncomfortable chill is cast not just by the ghosts of Sacco and Vanzetti who may still stalk its corridors or by the spirit of Friedrich Steinhoff, a German U-boat captain, held here after his capture by American sailors off the Azores in 1945. (He committed suicide with shards from his sunglasses.) Many in Boston remember more recent times of shame.

Riots were common in the early 1970s, when overcrowding meant cramming two inmates into a single cell. Inmates sued the city claiming inhumane conditions and after paying an unannounced night-time visit a disgusted local judge ordered it closed in 1974 without delay. However, it was another sixteen years before Boston completed building a new jail and the last inmates were transferred in May 1990. The building remained empty for the next 10 years, until Meyerson arrived with his vision of a luxury hotel.

His conversion – including the removal of two tons of pigeon droppings – was completed at a cost of $150m (£75m). Viewed from outside, the building has a bleak quality but also an impressive grandeur. There is a sense of permanence in the giant blocks of granite. They don't make 'em like this any more – prisons or hotels come to that. "At the time it was built, it wasn't considered pretty. It was just considered to be the way you did things were done with care and thought and great craftsmanship," explains Pam Hawkes, a preservation architect in Boston.

Fox Bryant also adorned his structure with high, circular framed windows that illuminated the jail. Today, shadows of its decorative mullions are projected on the high brick walls of the lobby as the sun travels from East to West. "I want people to gasp. I want people to have a 'Oh, my golly, this is amazing, [moment]" said Dick Friedman, the developer and co-owner of the Liberty.

As guests passed through the lobby to their croissants yesterday, their comments suggested he has succeeded. "Oh, neat," declares one, flashing pictures as she walks. "We are just looking," said another couple in cycling helmets who had apparently wandered in simply to gawp.

The dilemma of the developers in deciding whether to celebrate or mask the building's dubious history is evident inside. Eighteen of the 290 guest rooms are inside the original footprint of the jail. Ours retains some of the bare brick walls and some iron stubs of bars sawn away, but otherwise there are few reminders of former guests. No desperate messages scribbled on the brick, which has been blast-cleaned, or score-marks recording days held in confinement. The majority of the rooms are in a newly built brick tower with only subtle references to incarceration. Clink features a short parade of jail-cell doors and some of the original iron railings of the old catwalks encircle the atrium at higher levels. And while staff members bear numbers on uniforms, the hotel balked at dressing them in striped inmate outfits.

Meyerson reports visits so far by a few former employees, but so far no one has come in and identified themselves as former inmates. It will surely happen one day. Will Meyerson give them a good discount to spend a night in conditions rather better than those they'd known? He will not.

"They have had their free stay," he says.

Hotels with history

Four Seasons, Milan

In the heart of the Quadrilatero d'Oro district, this former convent is the hot ticket in Milan. Getting a room during the city's fashion week will take more than just devotion and prayers.

Malmaison, Oxford

The first prison-to-hotel conversion in Britain, this luxury boutique hostelry was home to Her Majesty's prisoners until 1996. It makes no attempt to disguise its past.

La purification, Mexico

A former 19th-century water-purifying centre in Puebla, this hotel, designed by renowned architect Ricardo Legorreta, is an adventure in minimalism. But there's nothing Spartan about the luxury guestrooms.

Four Seasons, Istanbul

In tourist-crammed Sultanahmet, this luxury hotel with just 65 rooms is housed in a former prison with turreted tower and open courtyard, is just steps from the Blue Mosque, and was built over a Byzantine palace.

Hotel Barcelona, Exeter

With modern furnishings and luxury trimmings, this Exeter hotel was once the West of England Victorian Eye Infirmary. The restaurant, the Café Paradiso, is contained in a circus-top structure.

Hopper Hotel, Cologne

In the late 19th and early 20th centuries, the Merciful Montabaur Brothers housed the bedraggled and homeless to bring them closer to God.