The Greek Isles Odyssey

Various photos courtesy of Ralph Lee Hopkins.

Nine islands. One legendary ship. Countless unforgettable moments. Members of The Club embarked on a remarkable expedition through the Cyclades aboard the National Geographic Orion, where private-access tours, exclusive tastings, and barefoot barbecues unfolded alongside ancient ruins and postcard-perfect sunsets. With expert guides, luxury comforts, and the kind of camaraderie only a shared journey can inspire, this was not just a trip — it was a story in the making.

Athens

The adventure began in the Greek capital, where Members were welcomed at the elegant Athens Capital Hotel. There was time to explore the historic heart of the city or simply relax at the rooftop bar before gathering for a welcome dinner at Dionysos Zonar’s, with views of the Acropolis lit golden at dusk.

A few early risers took part in a special sunrise tour of the Acropolis — before public opening — accompanied by a National Geographic photographer, calling it a “once-in-a-lifetime experience.” Others enjoyed small-group tours of the museums and ruins before regrouping at Papagiannakos Winery for a languid lunch, wine tasting, and the first toast of the trip.

And with that, it was time to board the Orion. The real adventure began at sea, with a toast on deck as the Temple of Poseidon faded into the horizon. A trip centuries in the making was officially underway.

Antiparos & Despotiko

The day began with a sunrise stretch — because it’s important to limber up before launching into sea caves via Zodiac. Ralph Lee Hopkins hosted an impromptu masterclass in photography, where even the most casual iPhone user walked away feeling like a National Geographic contributor.

Later, we dropped anchor at the Blue Lagoon. Cue the surprise floating bar, dispensing Ouzo Mojitos straight from the Zodiac. Back onboard, the Captain’s Welcome Dinner set the tone for the week: polished, indulgent, and likely involving another round.

Sifnos

Sifnos greeted us with blue skies and classic Cycladic charm. Early risers set off on a morning hike, while others opted for a walking tour of Kastro and the iconic 7 Martyrs Church, snapping photos along the way. Another group visited Narlis Farm for a hands-on farm-to-table cooking class, crafting traditional Greek dishes and feeding the farm’s friendly goats before enjoying the fruits of their labor.

In the afternoon, options included a pottery-making workshop where Members created their own bowls at the wheel while learning about local ceramic traditions, a seaside escape to Kamares for cocktails and swimming, or a Zodiac cruise to the dramatic Panagia Chrissopigi Monastery.

After dinner, the ship came alive for a high-energy Greek Night Party — think disco lights, sequins, and a photo booth brimming with playful props. Dressed in shades of blue, white, and plenty of sparkle, Members danced into the night to ABBA covers by the crew band, channeling full Mamma Mia spirit. An unforgettable evening at sea.

Milos

Milos greeted us with sea caves and sunbeams — a rugged postcard brought to life. At Kleftiko, the day began with sunrise kayaking through narrow inlets and silent coves, the only sound the splash of paddles. Afterward, we dove in straight from the Zodiac — crisp, salty, unforgettable — before returning to the ship for a long, lazy brunch on the deck.

The afternoon split the group in the best possible way. Divers went down into kaleidoscopic waters, spotting ancient pottery shards tucked between coral and curious schools of fish. Others explored the lunar-white landscape of Sarakiniko Beach, then wound uphill to Plaka’s cobbled lanes and the ancient amphitheater in Tripiti. That’s where sangria and Greek snacks appeared without warning — a low-key masterstroke of timing and hospitality.

Dinner was a choose-your-own-adventure: fresh-caught seafood in Plaka or a sunset dinner aboard the Orion. Either way, the view won.

Santorini

Santorini delivered its usual drama — but with some unexpected depth. The morning split into two paths: one group set off across the blackened terrain of Nea Kameni for a volcanic hike and swim in the mineral hot springs. The other stayed on terra-much-more-firma for a tasting tour at Nomikos Estate, where olive oils, capers, and sun-dried tomatoes offered a slower, more flavorful take on the island.

After a calm return to the Orion for lunch, the day shifted back into ancient history with visits to the Akrotiri excavation site — an archaeological marvel often compared to Pompeii — and the Museum of Prehistoric Thera, where elegantly preserved frescoes and artifacts told the story of a once-thriving Aegean civilization.

Dinner was held at Pyrgos, a family-run restaurant perched above the caldera. The setting alone would’ve been enough, but then came the lobster pasta, local wines, and, eventually, the dancers. Plates were broken (in the traditional, sanctioned way), music filled the room, and for a moment, everyone forgot about tomorrow’s schedule.

Dinner was held at Pyrgos, a family-run restaurant perched above the caldera. The setting alone would’ve been enough, but then came the lobster pasta, local wines, and, eventually, the dancers. Plates were broken (in the traditional, sanctioned way), music filled the room, and for a while, nothing existed beyond the joy of that moment.

Naxos & Paros

Naxos kicked off with a build-your-own-history morning. Some followed winding paths to the ancient Kouros statues, others made their way to the Portara — the monumental marble arch that greets the sea like an old friend. A few took the underwater route instead, snorkeling past curious fish, darting octopus, and a few sunken secrets best left to the imagination.

In Paros, things turned delicious. There was time to wander the postcard-perfect harbor of Naousa before heading to the Moraitis Winery, where four generations of island vintners proved they know their way around a bottle. At Petra Farm, hands-on took on new meaning: Members rolled dough, sampled fresh cheeses, and toasted with local wine under the late afternoon sun.

The day ended the way all days should: with a barefoot BBQ on deck, a sea breeze in the air, and laughter that lingered long past dessert.

Delos & Syros

Delos offered the rarest luxury of all: silence. Thanks to early access, Members roamed the mythic island alone, wandering through temples, mosaics, and marble ruins without crowds — or commentary. It felt less like a tour, more like time travel.

Syros flipped the script with grand architecture and unexpected glamour. A guided walk through Ermoupoli revealed ornate facades and a rhythm that felt more Italian Riviera than island village. The tour ended at Town Hall, where dancers in traditional Greek costume welcomed us with music and movement — and yes, we joined in. Back aboard the Orion, the Captain’s Farewell Dinner came with cocktails and a photo slideshow that captured the highlights better than words ever could.

Morning came, as it always does — too early and too final. Bags were packed, hugs were long, and plans for future reunions were floated over strong coffee. Some flew home, others kept adventuring, but everyone left with something permanent: salt on the skin, wine in the bag, and Greece lodged firmly in the heart.