Increasingly forested by glass towers and modern developments, Vancouver isn’t good at hanging on to its history. But one racy new tour aims to shine a light on the not-too-distant past by taking visitors behind the curtain at downtown’s infamous Penthouse strip club.

Opened in 1947, stars such as singing legend Frank Sinatra and actor Errol Flynn used to party at the glitzy venue. But when the golden age of glamour clubs began to fade in the 1960s, the Penthouse descended into liquor raids, vice squad visits and the 1983 gunshot murder of owner Joe Philliponi, known as the “Godfather of Seymour Street” after the club’s city centre location.

While contemporaneous Vancouver clubs have long since closed, the Penthouse – still run by the Italian-Canadian family that started it – has endured. And according to author Aaron Chapman, it now acts as a time capsule link to a period that intrigues many history-loving locals.

“There’s an appetite for Vancouver heritage right now and I think it’s because the city is changing before our eyes,” said Chapman, whose book Liquor, Lust, and the Law: The Story of the Legendary Penthouse Nightclub triggered the creation of the Secrets of the Penthouse tour.

For 38 Canadian dollars – which covers the tour plus a buffet dinner and a burlesque show by local troupe, Cabaret Torlage – Chapman and Penthouse owner Danny Filippone serve juicy tidbits from the club’s past as they walk groups through the venue. It was a time when patrons hid drinks in paper bags (the club belatedly received its liquor license in 1968) and the family illegally ran booze around the city in taxi cabs.

The tour takes in the disused Green Room, where Rat Pack crooner Sammy Davis Jr hung out and even slept over one night, and the labyrinthine upstairs area where the piano from the club’s former Steak Loft restaurant remains. Jazz musicians Louis Armstrong and Oscar Peterson once tickled its keys at a time when many other Vancouver venues barred black performers.

“Imagine yourself stepping back into the past,” Filippone said as he led groups past a faded poster of burlesque legend Big Fannie Annie and into the main bar and stage area. Here, the walls are studded with signed photos of Penthouse guests including Sinatra, American boxer Joe Louis and Brazilian singer Carmen Miranda.

“There are hardly any places in Vancouver with this kind of link to the past – especially one that includes bootlegging, strippers and a murder trial,” Chapman said. “But it’s because Vancouver is transforming so quickly that a strip club of all places can attract people with an interest in local history.”

The event, which runs on the first Thursday of the month, is organised by history-themed operator Forbidden Vancouver, which also runs additional guided tours around the city. Ticket are bookable online.

John Lee is the Vancouver Localite for BBC Travel