Bari, Piraeus, Izmir, Istanbul, Corfu, Bari

Bari, Puglia's ancient capital on the Adriatic, has served as a bridge between Western Europe and the Eastern Mediterranean for over two millennia — a heritage visible in the magnificent Basilica di San Nicola, one of medieval Christendom's most important pilgrimage churches, and in the labyrinthine Bari Vecchia where elderly women still hand-roll orecchiette in the street. The surrounding region of Puglia is among Italy's most compelling culinary destinations: burrata born in Andria, focaccia barese, and the puglian cuisine that has recently attracted international attention as Rome's and Florence's quieter, more authentic cousin. Visit April through June and September through October; the Trulli of Alberobello are forty minutes south.

The port that launched Athenian democracy's naval supremacy at the Battle of Salamis, Piraeus remains Greece's maritime heartbeat — and the most convenient gateway to both the Acropolis and the Aegean island chains. Dine on grilled sea bream at a Mikrolimano harbourside taverna, visit the extraordinary bronze Piraeus Apollo, and set sail for Hydra or Santorini by afternoon. Late April through June and September offer the Aegean at its most golden and uncrowded.

Izmir is Turkey's cosmopolitan Aegean capital, a three-thousand-year-old port city with a vibrant waterfront kordon, the labyrinthine Kemeraltı bazaar, and easy access to the ancient city of Ephesus. Must-do experiences include tasting boyoz pastries, exploring the Roman Agora, and day-tripping to Ephesus and its Library of Celsus. April through June and September through November offer the most pleasant temperatures for exploration.

For more than fifteen centuries, Istanbul has been the pivot upon which empires turned — Byzantium, Constantinople, the Ottoman capital — and nowhere else on earth compresses so much history into a single horizon. The Hagia Sophia, the Blue Mosque, and the Topkapi Palace form an incomparable trinity of architectural genius along the Golden Horn; the Grand Bazaar's four thousand shops offer a sensory immersion unlike any other marketplace. Must-dos include a Bosphorus sunset cruise and a meal of mezze along the waterfront at Karaköy. Spring (April–May) and autumn (September–October) offer the most gracious climate for this inexhaustible city.

Where Homer placed the island of the Phaeacians and four centuries of Venetian rule left their most enduring Mediterranean legacy, Corfu is a singular island of extraordinary historical depth and natural beauty. The UNESCO-listed Old Town — its narrow Kantounia alleyways, the elegant Liston arcade, and twin Venetian fortresses — is the finest preserved Venetian streetscape in Greece. Beyond the town, secret coves, olive groves of immense antiquity, and mountain villages offer weeks of unhurried discovery. May through June and September offer perfect conditions: warm sea temperatures, clear skies, and the island before or after its summer crescendo.

Bari, Puglia's ancient capital on the Adriatic, has served as a bridge between Western Europe and the Eastern Mediterranean for over two millennia — a heritage visible in the magnificent Basilica di San Nicola, one of medieval Christendom's most important pilgrimage churches, and in the labyrinthine Bari Vecchia where elderly women still hand-roll orecchiette in the street. The surrounding region of Puglia is among Italy's most compelling culinary destinations: burrata born in Andria, focaccia barese, and the puglian cuisine that has recently attracted international attention as Rome's and Florence's quieter, more authentic cousin. Visit April through June and September through October; the Trulli of Alberobello are forty minutes south.