On our last day in Greece, we found the sweetest spot. I was there with my spouse, Denise, floating in the crescent bay of historic Monemvasia. The sky was pure blue, and the warm water so clear we could see the rounded stones lining the sea floor.
We returned to the beach, where we’d left our things at a café table perched a few feet from the calm, rolling waves. We sipped Greek wine and ate olives and herbed tzatziki, and asked ourselves the question that bookends every magical trip: Why can’t we stay here forever?
Enchantment in travel often comes from expectations exceeded. For me, Greece has been on my to-do list for as long as I can remember. Enraptured by mythology and ancient tales, I had visions of this land and Aegean waters that I’d probably idealized. I envisioned dreamy light and air, and imagined delicacies involving phyllo dough and figs, served with house-made wines and ouzo. It all seemed so tantalizing that I made myself tamp down projections to let Greece reveal itself, without my eager idealizations.
Then we arrived, boarded a clipper ship, and discovered a mixture of sights and scenes that inspired and delighted us at every port.
We’d planned this voyage many months out as a belated honeymoon/ pleasure trip aboard the Star Flyer. As a modern-day sailing vessel, it promised an experience that harked back to classical times, when wind meant power and discovery. For us, it was an indulgent adventure with Star Clippers, a luxury cruise line, that offered rich experiences across five ports — Patmos, Amorgos, Mykonos, Monemvasia, and Kusadasi in Turkey.
The old-meets-new exploration by sail was instantly glamorous. We boarded in Athens, motoring out of the Port of Pireaus until the crew transformed our 360-foot-long vessel into a classic clipper. All four masts were suddenly rigged high with sails and jibs, the crew of expert sailors smoothly pulling and tying and knotting like seamless choreography.
At capacity with 170 passengers, we sailed toward the Northern Cyclades Islands, champagne in hand as we absorbed our first Aegean sunset. Our fellow travelers spanned all ages (though mostly middle-aged and up) and hailed primarily from England, France, and North America. It took no time to make social connections, including bartenders, servers, and friendly housekeeping crew. These would be our onboard family for the coming week, and a lively bunch they were.
Our first port of Kusadasi was a chance to set foot in Turkey, with some time in its touristic bazaars and along its waterfront promenade. But the main attraction was just outside town: Ephesus, a UNESCO World Heritage Site that’s one of the region’s best-preserved Greco-Roman cities. Its millennia-old architecture is gradually being restored stone by stone, mosaic by mosaic, and even in the hot Mediterranean sun it was hard not to continually stop and soak up its timeless wonder.
Both Kusadasi and our next port, Patmos, are Christian-pilgrimage sites related to Mary, who once lived there, and St. John the Evangelist. As such, each port stays busy with tourists, who thankfully don’t diminish the inherent charm.
Likewise, the small island of Amorgos, with some ancient history sites and quiet, winding lanes, was a compact place to feel the sleepy side of the Cyclades. Denise and I found ourselves wandering and enjoying the low-key vibes, stopping for frappes (a Greek cold coffee) and to take a cooling dip at each island’s scenic little beaches.
By the time we reached Mykonos, we’d forgotten all about our everyday world in New York, and surrendered to the mellow nature of Greece. This proved challenging on one of Europe’s most famous party islands, where in a blink we felt like we’d been dropped onto South Beach disguised as a picture-perfect Greek isle. It was jarring to be around so many people, in part due to the incredible queer population. Manscaped international males in short shorts and mirrored aviators reminded us of that other variety of cruising, and there were thousands of selfie-snapping tourists.
And still we loved it. We headed up the hill and strolled through quieter streets to reach the famous Windmills of Kato Mili and “Little Venice,” a row of wooden houses built precariously over the sea. We snacked on divine gyros at Sakis Grill House and sipped Aperol spritzes at Galleraki Bar, absorbing sights of glam travelers and the bright blue sea before us.
We took our time returning to the ship and were happily surprised to discover a hidden section of coastline behind a chapel, with a sightline back to our stately Star Flyer. We had but one more day to lie on board and soak up our ship’s grand views. So when we arrived at our final harbor of Monemvasia, we could savor it, even if we couldn’t stay there forever.
A Musical Sidenote: Sailing through the Greek Isles is magical enough, but some travelers may find its musical connection to “Mamma Mia” irresistible. In 2019, Star Clippers is offering four Eastern Mediterranean sails with a “Mamma Mia Itinerary,” docking in some of both films’ island locations. (Visit starclippers.com/us-dom/destinations/eastern-mediterranean-sailings.html.)
Athens with Ease: The Greek capital is an easy-access destination for cruises and flights. Coupled with its incredible sights and legendary ruins, it’s worth spending at least a few days there exploring the Acropolis, museums, boutiques and flea markets, and gorgeous rooftop and open-air restaurants. The city is great for LGBTQ travelers who frequent hotspots like Rooster in Plaka, Myrovolos in Metaxourgio, and the busy gay-centric neighborhood of Gazi.