Bari, Santorini, Piraeus, Katakolon, Cefalonia, 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.

Santorini, the ancient volcanic caldera rising from the Aegean, is Greece's most theatrical landscape — a crescentic island of sheer white cliffs plunging into an indigo sea, its clifftop villages of Fira and Oia draped in bougainvillea and culminating in the world's most photographed sunset. The island's unique Assyrtiko wine, grown on ancient ungrafted vines in volcanic pumice, is one of the Mediterranean's greatest expressions of terroir. Byzantine frescoes of extraordinary beauty fill the Prehistoric Museum of Thera. The volcanic black and red sand beaches of Perissa and Perivolos are unlike any others in Greece. April through June and September through October offer the finest conditions.

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.

Katakolon is the unassuming port that holds an extraordinary secret: just fourteen kilometres inland lies ancient Olympia, birthplace of the Olympic Games and one of the most sacred sites in the ancient world. The Archaeological Museum of Olympia — housing the breathtaking sculptures from the Temple of Zeus — ranks among Greece's finest, while walking the original stadium still sends a current of wonder through even the most seasoned traveller. The village itself charms with whitewashed tavernas and a relaxed pace that feels authentically Greek. Katakolon is best visited April through October; late spring and early autumn offer ideal temperatures for the Olympia excursion.

Argostoli is the capital of Kefalonia, the largest Ionian Island, renowned for dramatic geological wonders, pristine beaches, and the literary fame of Captain Corelli's Mandolin. Must-dos include visiting the subterranean Melissani Lake, admiring the cliffs of Myrtos Beach, and tasting Robola wine with fresh-grilled fish. May through October offers warm weather and calm seas, with June and September providing the best balance of conditions.

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.