For a more intimate experience of Athens, the charming Plaka District invites guests with its labyrinth of cobblestone lanes. Neoclassical architecture lines the narrow streets of the “Neighborhood of the Gods,” so named for its location. Browsing its shops or simply perusing its nooks and crannies are pastimes favored by visitors and locals alike. This historic area is the ideal setting in which to enjoy traditional small plates of meze and a sip of ouzo.

Crete was home to the Minoans, Europe’s earliest recorded civilization. Its capital, Heraklion, grew from the riches of the Venetian Empire, which ruled here for four centuries. Crete enjoyed a Renaissance building boom that helped bolster Heraklion as the region’s most strongly fortified city. The island is blessed with generous beaches, soaring mountains and coursing rivers. It is also where the distinct mantinades—couplets of love accompanied by Cretan instruments—could break out at any number of cafés where patrons sip tsikoudia, a grape-based brandy distilled in the hills.

Rhodes is home to the Palace of the Grand Master of the Knights of Rhodes, a remarkable fortification. Its historic quarter is Europe’s largest active medieval town. Outside the city, forests of pine and cypress blanket mountain slopes; vineyards and groves of citrus and olives soak up the Aegean sun. The Knights of Saint John of Jerusalem conquered the island in the 14th century, bringing great wealth from the Holy Land. Under their rule, the city was reconstructed to mirror the medieval ideal. Many of the buildings from this era remain and make for rewarding strolls.

One of antiquity’s best-preserved cities, Ephesus offers an unparalleled look into the lives of the ancients. Many of its ruins have endured from the time Ephesus was one of the largest metropolises of the ancient world. Excavations reach back to the 10th century BC, when this city hosted one of the Seven Wonders of the Ancient World—the Temple of Artemis. Today, Ephesus is still full of wonders: the towering facade of the Library of Celsus, the massive amphitheater that once sat 25,000 spectators and residences adorned with frescoes.

Çanakkale was an object of desire dating back to the ancient Greeks. Today, the nearby ruins of Troy, once a powerhouse of Asia Minor, provide a glimpse of the region’s former glory. The remarkably preserved structures of this UNESCO World Heritage Site offer hints of life here in the days of Alexander the Great and the later Roman Emperor Augustus. But it is the fabled Trojan Horse that is most prominent here. In Homer’s Iliad, the wooden steed gave ancient Greeks entry to the city during the Trojan War, and its legend is still very much alive today.

Istanbul exudes a fascinating mix of Western and Eastern cultures. Its strategic locale led to its role as a significant center of trade—eventually becoming a cultural crossroads along the world-famous Silk Road. One of the city’s stunning centerpieces is Hagia Sophia, founded as a basilica, converted to a mosque, then a museum; it is now a mosque again and features exquisite mosaics and frescoes. The city’s Grand Bazaar offers a rich taste of Turkish culture, from a vast selection of carpets and fabric to luscious dates and the local sweet favorite, Turkish Delight.