The Roof Lounge
Once a forgotten graveyard on the 18th-floor of the former Park Plaza Hotel, nearby University of Toronto students caught wind of an empty bar and colonised it. Eventually, it was revamped as a cigar lounge and the students migrated. Cuban cigars can still be smoked on the slender roof terrace for $40-$80 apiece (good luck getting a seat).
With its conservative aesthetic of green suede walls, mahogany furnishings and a fireplace, older men like to lounge on leather sofas, scotch in-hand. Bartender Joe Gomes has been here for 50 years now, dishing out drinks and advice to barflys.
Grateful recipients of his cocktails – including his signature Martini – have included every from John Wayne and Jane Russell, to Russell Crowe and Robert De Niro.