Athens (Piraeus) to Athens (Piraeus)

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.

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.

Mykonos is the Aegean at its most seductive — a labyrinth of bougainvillea-draped whitewashed alleys designed to disorient pirates (and occasionally visitors) leading to Kástro, the medieval hilltop quarter overlooking Little Venice, where balconied houses hang directly above the sea. The island's famous windmills, perched on a ridge above the old harbour, are best photographed at golden hour as pelicans patrol the waterfront below. Visit the sacred archaeological island of Delos — a 30-minute boat crossing — for one of the most significant ancient sites in the Greek world. May, June, and September offer the perfect balance of warmth, light, and bearable crowds.

Bodrum is the site of ancient Halicarnassus and one of the Seven Wonders, now a whitewashed Aegean resort town where the Knights Hospitaller castle houses the world's finest underwater archaeology museum. Visit June or September via Explora Journeys or Virgin Voyages for peninsula village dining, Bronze Age shipwreck treasures, and Turkey's most seductive balance of ancient heritage and contemporary Mediterranean sophistication.

Kuşadası owes its place on the world's cruise itineraries to one extraordinary proximity: the ancient city of Ephesus, one of the greatest metropolises of the Greco-Roman world, lies just seventeen kilometres from the port. Ephesus — with its two-kilometre marble colonnade, the Library of Celsus, and the Temple of Artemis (one of the Seven Wonders of the Ancient World) — demands at least half a day of unhurried exploration. The House of the Virgin Mary, a pilgrimage site believed to be where Mary spent her final years, adds a profound spiritual dimension. Kuşadası itself is a lively Aegean resort; the season runs April through October, with May and September offering ideal temperatures and smaller crowds.

Dikili is an unspoiled Aegean coastal town in western Turkey, serving as the gateway to the UNESCO-listed ancient city of Pergamon and the hilltop ruins of Atarneus where Aristotle once taught. Essential experiences include exploring Pergamon's dramatic acropolis, savoring fresh Aegean seafood at the harbor, and visiting the Roman thermal springs at Kocaoba. The best months are May and September for warm weather, clear light, and few crowds.

Bozcaada Island, Turkey, Turkey is a distinctive port city where deep cultural heritage meets authentic local atmosphere, featured on itineraries by Star Clippers. Must-do experiences include walking the historic center to experience the layered architectural heritage, and seeking out the regional culinary traditions at a locally favored establishment away from the port area. The optimal time to visit is May through September, when mild temperatures and long days favor unhurried 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.

Rhodes, Greece's resplendent Dodecanese jewel, merges a UNESCO-listed Medieval Old Town built by the Knights of St. John with sun-soaked Aegean beauty just seven miles from the Turkish coast. Wander the Street of the Knights before tasting *pitaroudia* fritters and local Athiri wine at an Old Town taverna, then take a catamaran to the neoclassical harbor of Symi. The island basks in over 300 days of sunshine annually, with April through June and September through October offering ideal temperatures for exploration without the peak-summer crowds.

Limassol is Cyprus's cosmopolitan coastal city, where a Crusader castle, revitalized old town, and spectacular modern waterfront meet the world's oldest named wine tradition in the nearby Troodos foothills. Visit year-round for the medieval heritage, Commandaria wine villages, and excursions to the ancient theatre of Kourion perched above the Mediterranean.

Haifa, Israel is a distinctive port city where deep cultural heritage meets authentic local atmosphere, featured on itineraries by Viking. Must-do experiences include walking the historic center to experience the layered architectural heritage, and seeking out the regional culinary traditions at a locally favored establishment away from the port area. The optimal time to visit is April through October, when warm weather and extended daylight create ideal conditions.

Ashdod is Israel's primary cruise port on the Mediterranean coast, an ancient Philistine city now serving as the gateway to Jerusalem, Tel Aviv, Bethlehem, the Dead Sea, and Masada. Must-do experiences include day trips to Jerusalem's Old City, exploring Tel Aviv's Bauhaus architecture and culinary scene, and visiting the archaeological remains of ancient Philistine settlements. Spring (March-May) and autumn (September-November) offer the most comfortable temperatures for touring.

Alexandria is the ancient Mediterranean port where the Great Library, Euclid's geometry, and the Pharos lighthouse defined Western civilization, now home to the stunning Bibliotheca Alexandrina and the multicultural Catacombs of Kom el-Shoqafa. Visit October through April via Oceania Cruises or Royal Caribbean for twenty-three centuries of layered history, optional Cairo excursions, and the city whose intellectual legacy surpasses most nations.

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.