Start with Greek coffee and loukoumades at Vanilla Café, then walk the caldera edge to Argylos for fresh pasta with local Cycladic produce. Lunch at Dimitris Taverna on the main plateia for traditional fava and grilled octopus. Afternoon stroll through side streets, stop at Espresso Corner for pastry. Sunset aperitif at Franco's Bar, then dinner at Selene for modern takes on island seafood.

Start before dawn at Ammoudi Bay to watch fishermen sell their catch to taverna owners. Breakfast at a cliffside café overlooking the caldera, then explore Oia's main street for lunch at a family taverna. Sunset at your chosen restaurant (book ahead), then walk back through empty streets after 10pm when crowds thin and locals reclaim the village.

Start at Nikolaos Taverna for a slow breakfast with Greek coffee overlooking the black-sand beach. Spend midday exploring the Ancient Thira ruins perched above town. By evening, wander Kamari's waterfront for fresh grilled octopus at Ouzeri to Kyma, then walk the black beach at sunset—quieter and more authentic than Oia.