Cyclades Cruise Itinerary: Santorini, Castles, and Caves

If you’re searching for a Cyclades cruise itinerary with a little more character, you’re in the right place. Jewels of the Cyclades began in Athens, but by Day 2, the Aegean had other plans. (Missed the start? Read Part 1 here.)

From Santorini’s blue-domed charm to Monemvasia’s medieval magic, every stop felt like theatre. A spontaneous detour to the caves of Mani turned this Cyclades cruise itinerary into a story at sea.

In this post, I share the second half of our small ship adventure. Think: island discoveries, volcanic flavours, unexpected weather turns, and a party sparked by a captive captain. It’s not your average Cyclades cruise itinerary. And that’s exactly why it’s unforgettable.

Saturday morning, the Aegean unveiled its treasure: Santorini. As part of our Cyclades cruise itinerary, we felt every wave in the tender, but once ashore, any discomfort vanished. Our first adventure was about to begin.

The cable car was out due to past seismic shifts. We relied on local bus drivers, who, by the way, are true pros on Santorini’s winding roads.

Akrotiri was our first stop on this Cyclades cruise itinerary. Thanks to Stella (our ever-organised Cruise Coordinator), we had it almost to ourselves. Our guide brought this “Greek Pompeii” to life with vivid stories and sharp humour, an exhilarating experience I’m still processing.

Next, we arrived in Oia. The magical hilltop town where the postcards come to life. The legendary Blue Church Domes stood before me, the majestic Caldera unfolding in a breathtaking vista.

The vibrant hues, the pure white walls crowned by those iconic blue cupolas – this is the visual symphony of Santorini. Though my lens couldn’t capture it all, one thing is certain. In Santorini, every snapshot, regardless of your skill or equipment, captures undeniable beauty.

Just a note while you’re here on your Cyclades cruise itinerary: please observe all “NO ENTRY” signs. It’s a simple way to respect both the locals and the strain that Santorini’s busy season brings. Thousands of visitors from March to November leave a bigger footprint than you think.

From volcanic beaches to local wine, Santorini offers something special for every kind of traveller.

Back aboard the elegant Galileo after our island lunch, we hoped the rough seas had calmed. No such luck! That evening, the Aegean made its presence well-known to everyone – the best treat of the night?

The ginger pills circulated faster than gossip, from the guests to the crew members alike.

Back in my cabin, the ship’s movement felt like a bumpy flight. If you’re a light sleeper, pack foam earplugs. They won’t block everything, but they can help you rest easier.

Our next port of call on this Cyclades cruise itinerary, the breathtaking Monemvasia, the Peloponnese’s first revealed treasure. Its name, meaning “the city with a single entrance,” hints at its singular charm. The ancient castle stands like a sentinel atop the peak.

Its presence intertwines with the modern town below, a powerful reminder of history woven into the present.

Just a quick five-minute bus ride from the marina, and we were standing at the gate of the castle town. We were fortunate to have the island’s best guide – in fact, the only one, ready to lead our exploration.

The moment I stepped through that ancient gate, it was like crossing a threshold into another realm. Reality seemed to fade behind me as the Venetian charm of every corner enveloped me.

Monemvasia’s link to the mainland is pure strategy — a human-made bridge jutting into the sea to foil pirate raids. As a result, there’s no seaward stair access. (Naturally, my inner explorer found a hidden gate near the main wall that did the trick.)

The heart of Monemvasia beats in its central square, a highlight of our Cyclades cruise itinerary. Home to the Byzantine church of Christ Elkomenos, it’s surrounded by a maze of narrow streets, full of charm. If you pause your wanderings, Malvasia Cafe offers a view that steals your breath.

Leaving the castle behind, we strolled into the new town for lunch and a curious sight: sun-dried octopodes. Why the sunbathing? It deepens the flavour, perfectly paired with a crisp glass of local white.

Afterwards, we were back on board by 18:00, we enjoyed a wine tasting and a special introduction by Fotini from Monemvasia Deli. She shared the legend of Mead, the fabled nectar of the gods, crafted from just honey and water.

Don’t leave Monemvasia without visiting their deli. You’ll find wines, liqueurs, olive oil, natural cosmetics, even olives and oils preserved in that golden honey blend.

At our 7 PM meeting with Stella, the conversation turned to tomorrow’s plan. Initial excitement may have been muted, but that didn’t last long.

By morning, every expectation would be blown away. After dinner, we turned in, curious about what lay ahead.

Our arrival in Gytheio at 7:30 AM marked the beginning of another beautiful stop on our Cyclades cruise itinerary. By 9 AM, we were exploring Mani, where the Diros cave awaited – a place that left me utterly speechless. We floated for 1.5 km through its watery veins, then walked for 300 metres.

Nature’s artistry was on full display. Water had carved the limestone into a breathtaking spectacle of stalactites and stalagmites.

We left the wonder of Diros cave behind and paused for coffee in the charming town of Areopoli. After a short wander, we reboarded the bus in search of the famous Caretta Caretta turtles. Sadly, they were elusive, leaving us to imagine a future sighting. So, onward we sailed.

Unfortunately, the weather and port authorities had other plans for Pylos. Instead, we spent the day exploring more of charming Gytheio. Everyone enjoyed an independent lunch.

Back onboard, we had a delicious baklava cooking class. Then came a lively ouzo party. We ended with a Greek buffet worth writing home about.

With ancient weather rituals in mind, our guests took matters into their own hands (literally). Therefore, a “sacrifice” was deemed necessary. They playfully tied up Captain George, our ever-good-humoured captain, sparking a party that quickly became legendary.

Whether the gods were amused is unclear. However, by midnight, the engines roared to life and we were off again, laughter still echoing through the decks. Captain, thank you for your contribution.

To sum up, this Cyclades cruise itinerary offered more than scenic views and sun-drenched days. It gave us unexpected detours, deeper connections, and a front-row seat to Greece’s quieter wonders.

From Santorini’s iconic vistas to the haunting beauty of Diros cave, each stop told its own story. If you’re considering a small ship adventure that balances comfort with discovery, this Cyclades cruise itinerary might be for you.

Ready to experience Jewels of the Cyclades for yourself? Click here to request a quote or book your Cyclades cruise itinerary.
Curious how it all began? Read Part 1 of the journey here.
Want to keep sailing? Part 3 is waiting for you.