Sailing trip Cyclades

White villages on dark rocks, deep blue sea and the local Meltemi wind: the Cyclades are the heart of the Aegean. With Sailing-Classics you sail from Santorini via Ios, Amorgos, Paros and Folegandros through one of the most impressive island worlds in Greece – intense, authentic and with true Aegean character. Our Cyclades cruises usually start and end on Santorini and pass through the southern and central islands of the region. The route combines spectacular volcanic landscapes, small harbour towns, secluded bays and longer stages under sail – ideal for anyone who wants to experience Greece and an active life on board.

Santorini is the dramatic prelude and impressive conclusion to your trip. The towering crater walls of the caldera, formed by a massive volcanic eruption, rise imposingly out of the deep blue sea. The whitewashed villages of Fira and Oia, whose houses nestle against the cliffs like paintings, are enthroned high above the rocks. From the water, Santorini has a very special effect: the contrasts of dark volcanic rock, white villages and bright Aegean blue are unique. Whether entering the caldera or sailing out into the open sea – Santorini is one of the most impressive sailing moments in Greece.

Amorgos is one of the most pristine and impressive islands in the Cyclades. Steep rocky coasts, deeply indented bays and the spectacular Hozoviotissa monastery built into the rock face characterize the picture. The island appears rougher, quieter and less touristy than many of its neighbours – which is precisely what makes it so appealing. Here you can experience the Aegean in its purest form: clear air, wide horizons and the feeling of freedom. Anchor stops off secluded bays offer ideal conditions for swimming stops, while small villages in the interior of the island convey authentic Greek life.

Paros combines traditional Cycladic architecture with lively but pleasant harbour life. In places like Naoussa, you can expect winding alleyways, small tavernas and an authentic yet stylish ambience. At the same time, the island offers numerous sheltered bays with clear water – ideal for relaxing anchorage breaks.

Ios completes the route with a mixture of spectacular beaches, rolling hills and charming villages. Away from the well-known places, you will discover quiet anchorages and spacious bays that are perfect for extended swimming stops and relaxed evenings on board.

Folegandros is an insider tip among the Cyclades islands. The small, elevated Chora is one of the most beautiful in Greece: whitewashed houses, small squares and narrow alleyways create a tranquil, almost timeless atmosphere. From here you can enjoy sweeping views over the sea and the surrounding islands. The island is much quieter than many other destinations in the Aegean and offers a special blend of originality and elegance. Folegandros stands for the authentic, unadulterated Cycladic feeling – far away from the hustle and bustle, with plenty of space for tranquillity and intense impressions.