The most happening street in downtown Cape Town, Long Street has founded a great recipe for socially-oriented; a Bohemian feel with just the right mix of trendy, Victorian buildings with balconies overlooking the road. This is where folks go out in Cape Town; it's also where we'd expect to see you.
The offerings available on Long Street are quite diverse. There's the typical Irish pub that is always packed (The Dubliner), the club known for progressive sounds (Fiction), uber-hip lounge (Julep), the up-and-coming rock club (Aces n Spades), and the usual hidden-away dive that is worth the trouble to find (Waiting Room, located above the Royale Eatery).
Speaking of, the burgers at Royale Eatery are excellent, while Neighbourhood has good food to accompany your people-watching from the second floor balcony, and a slew of pizza places (apparently this is the "drunkfort food" that people fall back on all over the world).