South Yarra, Prahran & Windsor

These suburbs are Melbourne's perennial cool kids. While the South Yarra end of Chapel St has sold its soul to high-street chains and is frequented by locals in activewear and oversized sunglasses, the Prahran and Windsor end has more grunge appeal thanks to some fantastic restaurants, interesting bars and street art. Not to be missed on the northwestern edge are Melbourne's showpiece Botanic Gardens, while Prahran is home to an extraordinary private-house museum of art and a market that's as good for lunch as it is for produce shopping.