Are you hip enough for Brighton? It's the only city in the UK with a Green Party MP. Brighton's only 45 minutes from London by train with an incredibly diverse, hippy community, featured in cool films like Quadrophenia.
The Royal Pavilion is iconic, the Lanes are great for crafty shoppers, the Grand Hotel a landmark made more famous by the 1980s IRA bombing of Mrs Thatcher's cabinet and of course the beach and Pier which are filled with locals and tourists alike on sunny days. London to Brighton rallies also feature regularly, with classic cars, bikes and motorcycles often seen promenading along the seafront; and the nightlife is legendary.
Brighton can feel like a small town, but the extended built up area including the Sussex towns of Worthing, Hove and even Littlehampton adds up to a population of 480,000. It's also the UK headquarters of American Express.