Gleaming white houses and blue-domed buildings perched on soaring cliffs above the sparkling Aegean Sea—it must be Santorini, a distinctly picturesque island among the many-splendored Greek Isles. Roam the palapa-shaded black sands of Perissa Beach or ogle the dramatic sunsets of cliff-top village Oia, one of the most photographed spots in the world.

Where to Stay: Oia’s Katikies Hotel overlooks the sweeping caldera basin with 27 whitewashed cubist cottages situated around two infinity pools.