21 Club
Follow the trail of jockeys into one of America's most famous surviving speakeasies. Opened in 1930, the multifaceted space has welcomed everyone from Frank Sinatra and Ernest Hemingway to presidents and politicians - ironic considering its illicit beginnings. Humphrey Bogart was apparently such a regular that table 30 is now called "Bogie's Corner."
21 Club, 21 W 52nd St.
[Photo via @21club]