1. Oia
Best for: sunsets and chic hotels
With its caldera-edge hotels, ritzy tavernas and marble-paved streets, romance hovers like a heart-shaped cloud over Santorini’s most popular sunset spot. Shop ‘till you drop in the whitewashed labyrinth of Oia’s streets before following crowds to Oia’s clifftop castle to watch the sun set in a scarlet blaze over the volcano’s rim. Celebrate with a dry Negroni at funky bar Hassapiko, then order wine-doused prawns and other treats at atmospheric caldera-edge taverna 1800- Floga.
Stay here: For spectacular caldera-edge sleeps stay in a River suite at Canaves Ena. Away from the crowds, prefer Santo Mine Oia suites.