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The 178-year-old prison has been a massive fortress on the Kingston waterfront. Plans by Correctional Service Canada to decommission it in 2015 have stirred local imagination.Frank Gunn/The Canadian Press

The men set out on an overcast spring day in a Zodiac boat, navigating the choppy waters of Portsmouth Olympic Harbour as they ogled the waterfront and schemed the fortress's future.

The magnitude of Kingston Penitentiary's frontage confirmed, in their minds, that the property is ripe for a total re-imagination.

Down with the imposing boundary walls that once isolated the likes of Paul Bernardo and Clifford Olson. Up with residential units, restaurants and retail space. Up, importantly, with what the Kingston mayor deemed an "intriguing" feature: an international sailing centre to solidify the Ontario city as the freshwater sailing capital of the world, improve Canada's chances of winning Olympic medals and attract people to the sport.

"This all started at the end of my driveway," said George Hood, a former Queen's University vice-principal who grew up sailing and raced competitively. "We were talking one night and we said, 'Well, somebody should figure out what the hell to do with Kingston Pen.' And one thing led to another."

In early 2012, "we" was himself and 1976 Olympic sailor Michael de la Roche. But the "we" has grown to include Queen's University's meeting facilitator, former racer George Jackson; and John Curtis, a Kingston lawyer and 2004 Olympic sailor who, along with Mr. Hood, got an audience in May with a cabinet minister's staff in Ottawa to discuss the proposal.

No longer a working prison as of last month, the property would be transformed into a mixed-use development that could retain heritage structures such as the front gate, the main dome and the north cell block. The $50-million sailing centre would boast dormitories, fitness facilities, a 300-foot-wide launch ramp, training programs, a fleet of boats and, perhaps, an indoor tank so rowers could train in the off-season.

"The concept sounds very intriguing," Mayor Mark Gerretsen said, adding that the plan does not explicitly require city hall's approval, but would need council's backing for rezoning. "I'm very optimistic."

It's early days – the penitentiary will not be decommissioned until 2015, Correctional Service Canada (CSC) has not decided what to do with the property, and multiple federal government departments could be involved in any lease, sale or transfer.

It is unclear how heritage designations for most of the prison buildings will complicate future plans, and other proposals must be considered.

There have been lofty thoughts of preserving the penitentiary as an "Alcatraz North." More than 9,000 people bought tickets this month for tours in support of the United Way, but the reality is that Ottawa shuttered the outdated prison because it is too costly to maintain.

There have been murmurings in the pages of The Kingston Whig-Standard of incorporating a casino into a future plan.

And former warden Monty Bourke said some people want the prison levelled to erase it from the city's collective memory.

Residents of neighbouring Alwington Place have asked Mr. Hood's group, "how high are you going to go?" with the proposed 500 high-end condo units, but the sailing vision – which proposes low- or mid-rise units, not towers – nonetheless appears to be the idea with the most momentum.

Public meetings about creating an international sailing centre in Kingston have attracted upward of 150 people at a time, and the proponents are planning an invitation-only presentation in Ottawa for CSC, Sport Canada and a few other departments.

Jeff Garrah, CEO of the Kingston Economic Development Corp., deemed the proposal "worth exploring" because the city played host to the sailing events for the 1976 Montreal Olympics and is home to the annual Canadian Olympic-training regatta in Kingston (CORK).

Even the Friends of the Penitentiary Museum, a non-profit that wants key structures maintained as an experiential museum, said the sailing vision does not necessarily contradict their own. And Mr. Curtis said he and Mr. Hood felt their proposal got a good reception at the May meeting with two of Treasury Board President Tony Clement's staffers, one of whom had recently attended the America's Cup in San Francisco.

Mr. Clement's acting director of communications, Aaron Scheewe, said the office is "very much aware" of the proposal, but said the discussion about the property – assessed at $17.6-million – was routine.

"If someone calls and has a legitimate proposal they put forward, it's our obligation to hear them out," he said.

Since the chat on Mr. Hood's driveway last year, the sailing group has hired U.S. architects Norris Strawbridge and Gary Anderson – who designed the 2004 Olympic sailing site in Athens – and enlisted the services of government relations firm Hill & Knowlton.

They've also received formal letters of support from Sail Canada, CORK, Ontario Sailing, and the Canadian Olympic Committee.

"I think it's got a lot of potential and a lot of traction," Mr. Bourke said, adding that he hopes Friends will get approval to run regular tours next year while Ottawa mulls its options.

"Let's just tell our story the way it is: the good, the bad, the sad, the famous, the infamous. That's our history, whether we like it or not."