Santorini’s caldera-edge towns involve real walking on stepped, uneven paths — especially in the older sections of Oia and Fira, where conventional streets give way to narrow stairways connecting different cliff levels. Sturdy sandals or light shoes with real grip will serve you far better than typical beach flip-flops, which become a genuine liability on the steeper stretches.
Light, breathable clothing suits the warm, sunny climate that defines most of the travel season. Sun protection — hat, sunglasses, sunscreen — is a practical necessity here, given how much light bounces off both the white-washed buildings and the caldera water itself.
Evenings, especially the famous Oia sunset, can bring a real breeze even after a warm day. Worth carrying a light cardigan or jacket for comfort, since you’ll likely be standing or sitting in an exposed spot for a while before and during sunset.
No specific cultural dress code beyond standard beachwear norms — the island’s beaches include both conventional sand and the distinctive black volcanic sand variety, and both follow typical Greek island conventions.