Mykonos Town, known locally as Chora, is the quintessential Cycladic village amplified to dazzling effect. A maze of narrow, winding lanes paved with whitewashed stone leads past sugar-cube houses with brilliantly painted doors and shutters in cobalt blue, scarlet, and emerald green. Cascading bougainvillea spills over balconies, and around every corner there seems to be another tiny chapel, a hidden courtyard draped in jasmine, or a boutique selling handmade jewelry. The town’s deliberate labyrinthine design was originally intended to confuse the pirates who frequently raided these islands, and today it delightfully disorients visitors who happily wander without a destination.

The waterfront area of Little Venice, where medieval houses hang directly over the sea with their wooden balconies practically touching the waves, is one of the most photographed spots in all of Greece. Nearby, the iconic row of 16th-century Kato Mili windmills stands on the ridge above the harbor, their thatched caps silhouetted against the Aegean sky. As the sun sets, Little Venice transforms into a magical theater of color, and the bars lining the waterfront fill with visitors sipping cocktails as the sky turns from gold to pink to deepest purple. After dark, Mykonos Town becomes one of the most vibrant nightlife destinations in the Mediterranean.

Pro tip: Visit the Paraportiani Church, a cluster of five tiny whitewashed churches merged into one asymmetric sculptural form, early in the morning when you can appreciate its organic beauty without the selfie crowds. For dining, skip the overpriced waterfront restaurants and head inland to the area around Ano Mera square or ask locals for their favorite family-run taverna serving fresh-caught fish.