Sailing from Paros to Santorini

Adventure

7-day itinerary with a grand finale in Santorini

Destination: Cyclades, Greece | Duration: 7 days/7 nights | Embarkation: Paros | Disembarkation: Paros | Islands: Cyclades, Paros, Skinoussa, Koufunissi, Keros, Iraklia, Ios, Amorgos, Santorini | Option: Exclusive skippered charter or cabin charter | Highlights: Coastal sailing, exploring bays, authentic villages, Santorini caldera

An extraordinary journey through the crystal-clear waters of the Aegean, from the coasts of Paros to the volcanic magic of Santorini. This sailing cruise in the Cyclades will take you through the Small Cyclades, still authentic and untouched gems, before continuing on to Ios and reaching its scenic destination amidst the calderas and cliffs overlooking the sea of ​​Santorini.
At times challenging navigation on a fast and fun boat alternates with days of total relaxation in remote bays, swimming in turquoise waters, and evenings in timeless Greek tavernas. Every sunrise brings a new island, every sunset tells a different story.

Price and Available Dates : 29 AUGUST 2026 o see the 2026 cruise program. Services Included  Full Details: Charter term and Condition Walkabout Charter

⭐⭐⭐⭐⭐Rating: 4.9/5 (basato su 47 recensioni Google, TripAdvisor e Facebook)

Sailing Adventure

Day by day itinerary

Boarding in Paroikia and first night in Antiparos

SATURDAY The journey begins in the late afternoon in Paroikia, the main port of Paros, with its characteristic open bay and lively promenade. After boarding the Walkabout 43, a welcome toast breaks the ice: we introduce ourselves and settle our luggage in the cabins. As the last light of sunset tints the hills of Paros orange, we cast off for a short sail towards Antiparos. It’s time to dive in for the first swim of the holiday in the clear waters of the strait between two small islands. This is the welcome the Aegean Sea reserves for those who know how to wait for it. The evening ends at anchor, with dinner prepared on board by the skippers. Table set in the cockpit, stars overhead, and the silence of the sea all around: a perfect start to the cruise.

Sailing towards Schinoussa

SUNDAY We leave Antiparos early in the morning, heading for Schinoussa, one of the lesser-known gems of the Small Cyclades. The sailing, with the wind typically on the beam or a broad reach, promises to be fast and engaging: great for those who want to take the helm or learn how to use the sails. Schinoussa is an island that mass tourism hasn’t reached yet. The roads are still partly unpaved, and the pace of life is sleepy and peaceful. 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 an afternoon of relaxation between swimming and reading. In the late afternoon, a panoramic walk takes us to the Chora for an aperitif in one of the small outdoor bars, where the colors of the island and the evening breeze make everything more beautiful. Dinner on board, cooked by the skippers with fresh local products, rocked by the quiet of the bay.

Koufonissi: white beaches and a lively evening

MONDAY A short and pleasant sail towards Koufonissi (or Kato Koufonissi), the smallest and most vibrant island of the Small Cyclades. Here, the sea reaches shades of turquoise and emerald that are hard to forget. The day is dedicated to pure relaxation: we drop anchor a few meters from a fine white sand beach, in very shallow and transparent waters. The afternoon passes with swimming, snorkeling, and siestas in the shade of the sail. In the late afternoon, we move to Koufonissi for a more worldly evening. The island has a double character: quiet and genuine by day, lively and welcoming by night. Dinner in a typical tavern at the port, featuring grilled fresh 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 of the entire cruise awaits us: Keros. A remote and uninhabited islet, Keros is one of the most important archaeological sites in the Aegean: thousands of Cycladic marble idols, now exhibited in the world’s major museums, were found here. The sail from Koufonissi is short but often intense, with the Meltemi blowing strongly between the islands. We anchor in deep blue waters, surrounded only by rock and silence. Lunch on board and long swims in this wild and uncontaminated corner of the sea. In the evening, the sky—far from any light pollution—transforms into a spectacle: shooting stars, the Milky Way, and the constellations that Greek sailors learned to read millennia ago. Dinner on board, under this very sky.

Iraklia or Amorgos: sailing where the wind takes us

WEDNESDAY Today’s stop depends on the weather conditions. If the wind and sea allow, we push on to Amorgos, the wild and fascinating island of the Cyclades; alternatively, we remain in the Small Cyclades archipelago and head for Iraklia. Amorgos: An arid and rocky island, where the deep blue of the sea contrasts with the barren landscapes and the austere beauty of the territory. We anchor in the large bay of Katapola and in the afternoon venture towards 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 the warm welcome of 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 only one equipped beach, a tiny port, and paths leading to hidden coves accessible only on foot or by boat. We anchor in a quiet corner and the day flows between swimming, reading, and the pleasure of doing nothing in a wonderful place. Dinner on board or in one of the rare local taverns.

Ios

THURSDAY Today we sail towards Ios, an island with a dual character: wild and mountainous in the south, where remote bays are accessible only from the sea, and worldly and lively in the Chora to the north, famous throughout the Mediterranean for its nightlife. We anchor in one of the magnificent bays in the south of the island, accessible only by boat: lunch in the cockpit with eyes wide open to a landscape that looks like a painting. The afternoon is all ours for swimming and relaxation. In the late afternoon, we head back up towards the port and treat ourselves to a walk in the Chora of Ios, perched on the hill with its white alleys and blue churches. For those who wish, the evening can be spent enjoying true Greek cuisine in one of the port’s taverns, with grilled fresh octopus and house wine.

Arrival in Santorini: the grand finale

FRIDAY The final navigation takes us to Santorini, one of the most iconic and scenic places in the Mediterranean. As we approach, the sheer black cliffs plunging into the sea begin to loom on the horizon: the thrill of arriving by boat, slowly and without haste, is something unique. We sail through the Santorini caldera from north to south, passing under the imposing volcanic walls and admiring the white villages of Oia and Fira clinging to the cliffs. A sight that no photograph can truly capture. We anchor in front of Akrotiri beach, in the south of the island. From here, those who wish can visit the famous archaeological site of Akrotiri, the “Pompeii of the Aegean,” or simply enjoy the nearby red sand beach. The evening is our last one together: a farewell dinner ashore in a Greek tavern, amidst toasts and memories of a week spent between wind, sea, and unforgettable islands. SATURDAY Breakfast on board and disembarkation in Santorini. The holiday ends here, but the Cyclades stay with you. Desideri che inserisca anche dei meta tag SEO (come title e description) per questa pagina?
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How to Book

  • Personalized Quote: Receive within 24h: detailed quote, confirmed availability, contractual conditions.
  • Confirmation: Pay the deposit to secure your booking.
  • Book flights: Walkabout Charter provides info for flights, ferries, and transfers.
  • Trip Preparation: Receive a recommended equipment list and communicate any special dietary requirements.
  • Boarding! Your adventure in the Sporades begins!

The lesser-known Cyclades and spectacular Santorini. Walkabout Charter takes you there!!

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