Star Clippers Unveils Four New Itineraries in Greece for Summer 2027
There’s something presumptuous about wanting to follow in the footsteps of Odysseus. The Greek gods of the sea have never been kind to travelers in a hurry. Star Clippers, which is offering four new sailing itineraries through the Greek islands aboard the Star Flyer for the summer of 2027, seems to have understood this. These cruises aren’t designed to see Greece—they’re designed to experience it.
What Large Ships Cannot Reach
The Star Flyer, a four-masted schooner with sails spanning more than 1,600 square meters, doesn’t resemble the cruise ships that disgorge thousands of passengers onto the docks of Santorini every morning. It embodies a different kind of promise: the promise of sailing into bays that large ships cannot reach, of anchoring off villages that have remained untouched by mass tourism, and of watching the sunrise from a teak deck without the view being blocked by other travelers’ cell phones.
The four itineraries announced have names that evoke travel literature more than tour operator catalogs. “Authentic Greek Getaway,” “Odyssey of the Greek Islands,” “Jewels of the Aegean,” “Timeless Cyclades”. These titles are no marketing fluke. They signal an editorial intent—that of restoring to Greece a complexity that overtourism tends to flatten.
The Islands You Won’t Find in Guidebooks
Among the new destinations, Astypalea is well worth a visit. Nicknamed “the butterfly of the Aegean” for its distinctive shape when viewed from the sky, this island in the Dodecanese is one of the archipelago’s best-kept secrets. Its landscapes reflect a Greece still unconcerned with its image—a white chora perched on a promontory, half-collapsed windmills, and coves reached on foot after crossing hills parched by the summer heat.
Ouranoupoli, the gateway to Mount Athos, lends an almost spiritual dimension to the itinerary: you cannot enter the monastic peninsula—the ecclesiastical authorities rarely grant permission—but you can catch a glimpse of its towers from the sea, and something of that mystery is conveyed to the eye. Chania, a Venetian port in western Crete, has preserved its Ottoman mosques, its Venetian arsenals, and its winding alleys, whose intertwining layout tells the story of five centuries of successive occupations without betraying any of them. And Çeşme, a Turkish port on the Aegean coast, serves as a reminder that the eastern Mediterranean has never truly had a natural border between Greece and Anatolia.
The Pedagogy of Slowness
What Star Clippers offers with these itineraries is not a cruise product. It is a lesson in slowness. The speed of a sailboat demands a kind of patience that is not a constraint—it is a discipline. You arrive when you arrive, depending on the wind and the sea. And this uncertainty, in a world where everything is optimized to arrive on time, has something strangely liberating about it.
Andros, the northernmost of the Cyclades, which is also included in these new itineraries, reminds those who may not yet know that it is home to one of the best contemporary art museums in all of Greece. This detail sums up quite well what Star Clippers is trying to sell: not a destination, but a way of being somewhere.
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