Built in 1927, the neo-Gothic structure of the Windsor Arms was intended to resemble the buildings of the University of Toronto. (The hotel is near Victoria College at the university.) The entrance feels like stepping into a castle, the Windsor Arms logo perched neatly beside the portico, doorman at the ready. The hotel was purchased by developer George Friedmann in 1995 and resurrected with modern touches for a fresh debut in 1999. The hotel is birthplace to the idea of the now-famous Toronto International Film Festival (TIFF). It continues to attract celebrities who want a boutique feel, and though TIFF has shifted its headquarters south, the Windsor Arms will always be a refuge for those who want Old World charm and exclusive service. The streetside patio is perfect for people watching during the lively month of September. And in the hotel’s hallways, you can “stargaze” at the portraits of celebrities, from Robert Redford to Barbra Streisand.