Sailing from Paros to Santorini

Embarkation in Parikia and first night in Antiparos

SATURDAY

The journey begins in the late afternoon in Parikia, the main port of Paros, with its characteristic open bay and lively waterfront. After boarding the Walkabout 43, a welcome toast breaks the ice: we introduce ourselves and stow our luggage in the cabins.
As the last rays of sunset paint the hills of Paros orange, we cast off for a short sail to Antiparos. It’s time to dive in for the first swim of the holiday in the clear waters of the strait between two islets. It’s the welcome the Aegean Sea reserves for those who wait.

The evening ends at anchor, with dinner prepared on board by the skippers. A table is set in the cockpit, the stars overhead, the silence of the sea all around: a perfect start to the cruise.

Sailing to Schinoussa

SUNDAY

We leave Antiparos early in the morning, heading for Schinoussa, one of the lesser-known gems of the Small Cyclades. The sailing, typically with a beam or close-hauled wind, promises to be fast and engaging: perfect for those who want to take the helm or learn to sail.

Schinoussa is an island untouched by mass tourism. The roads are still partly unpaved, the pace of life sleepy and tranquil. The Chora, a handful of white houses along the main road, transports visitors to another era.

We anchor in the splendid bay of Livadi for lunch on board and a relaxing afternoon of swimming and reading. In the late afternoon, a scenic stroll takes us to the Chora for an aperitif in one of the outdoor cafés, where the colors of the island and the evening breeze make everything even more beautiful.

Dinner on board, cooked by the skippers with fresh local produce, lulled by the tranquility of the bay.

Koufonissi: white beaches and a lively evening

MONDAY
A short and pleasant sail to Koufonissi (or Kato Koufonissi), the smallest and liveliest island of the Small Cyclades. Here, the sea takes on unforgettable shades of turquoise and emerald.
The day is dedicated to pure relaxation: we drop anchor just a few meters from a fine white sandy beach, in shallow, transparent waters. The afternoon is spent swimming, snorkeling, and siestas in the shade of the sail.
In the late afternoon, we move to Koufonissi for a more social evening. The island has a dual character: tranquil and authentic by day, lively and welcoming by night. Dinner in a typical taverna on the harbor, enjoying fresh grilled fish and local wine, in the company of fishermen and the lucky few who have discovered this corner of Greece.

Keros: the island of gods and silence

TUESDAY
Today, one of the most exciting stops on the entire cruise awaits us: Keros. An uninhabited and remote islet, Keros is one of the most important archaeological sites in the Aegean: thousands of Cycladic marble idols were discovered here, now exhibited in major museums around the world.
The sail from Koufonissi is short but often intense, with the Meltemi blowing forcefully between the islands. We anchor in deep blue waters, surrounded only by rocks and silence. Lunch on board and long swims in this wild and pristine corner of the sea.
In the evening, the sky, free from any light pollution, transforms into a spectacle: shooting stars, the Milky Way, the constellations that Greek sailors learned to read millennia ago. Dinner on board, under this same sky.

Iraklia or Amorgos: we sail where the wind blows

WEDNESDAY
Today’s stop is weather-dependent. If the wind and sea permit, we’ll sail to Amorgos, the wild and captivating island of the Cyclades; alternatively, we’ll stay in the Small Cyclades archipelago and set sail for Iraklia.
Amorgos: A barren and rocky island, where the intense blue of the sea contrasts with the barren landscapes and austere beauty of the land. We’ll anchor in the large bay of Katapola and in the afternoon, venture to the famous Hozoviotissa Monastery, nestled in the rock 300 meters above the sea. The nearly 400 steps leading to the entrance are rewarded with a breathtaking view and a warm welcome from the monks, who offer guests a glass of Rakomelo and fruit sweets. One of the most unforgettable experiences in the entire Aegean.

Iraklia: the smallest and least visited of the Small Cyclades. An island of absolute peace, with a single equipped beach, a tiny harbor, and paths leading to hidden coves accessible only on foot or by boat. We anchor in a quiet corner and the day passes with swimming, reading, and the pleasure of doing nothing in a wonderful place.

Dinner on board or in one of the few local tavernas.

Ios
THURSDAY
Today we sail to Ios, an island with a dual character: wild and mountainous in the south, where remote bays are accessible only by sea, and cosmopolitan and lively in the Chora in the north, famous throughout the Mediterranean for its nightlife.
We anchor in one of the island’s magnificent southern bays, accessible only by boat: lunch in the cockpit, gazing at a panorama that seems like a painting. The afternoon is all ours, swimming and relaxing.

In the late afternoon, we head back to the port and take a stroll through the Chora of Ios, perched on the hill with its whitewashed alleys and blue churches. For those who wish, in the evening you can enjoy authentic Greek cuisine in one of the port tavernas, with fresh grilled octopus and house wine.

Arrival in Santorini: the grand finale
FRIDAY
The final sail takes us to Santorini, one of the most iconic and scenic places in the Mediterranean. As we approach, the black cliffs overlooking the sea begin to loom on the horizon: the thrill of arriving there by boat, slowly, unhurriedly, is something unique.

We sail through the Santorini caldera from north to south, passing beneath the imposing volcanic walls and admiring the white villages of Oia and Fira clinging to the cliffs. A spectacle no photograph can truly capture.
We anchor off Akrotiri beach, in the south of the island. From here, anyone can visit the famous archaeological site of Akrotiri, the “Pompeii of the Aegean,” or simply enjoy the nearby red-sand beach.
This evening is our last together: a farewell dinner ashore, in a Greek taverna, with toasts and memories of a week spent amidst the wind, sea, and unforgettable islands.

SATURDAY
Breakfast on board and disembarkation in Santorini. Your vacation ends here, but the Cyclades remain with you.