1. Chania
Best for: culture and nightlife
With its picturesque Venetian harbour surrounded by historic mansions repurposed as ritzy boutique hotels (including my favourite Casa Delfino), Chania is the island’s most atmospheric city. Soak it up in the warren of shopping lanes behind the harbour where stores sell everything from handcrafted jewellery to traditional stivani boots, before admiring nautical treasures in the maritime museum or gawping at Minoan wonders in the new archaeological museum.
When hunger bites, sample streetfood at the city’s food market, or feast on local fare at Mezedopoleio Halepa or Salis. End your day with a syrupy mastixa cocktail at historic bar Synagogi, or party the night away at hip beach club Cabana.