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 harbor towns, secluded bays and longer stages under sail – ideal for anyone who wants to experience Greece and an active life on board.
Sailing between Santorini, Ios, Amorgos, Paros & Folegandros
Dramatic rocky coasts, white villages & deep blue Aegean waters
Sportier area with real wind character
The Cyclades are one of the windiest areas in Greece. The Meltemi, a dry northerly wind, ensures constant conditions and clear visibility, but can freshen up considerably in midsummer. Longer distances between the islands make the area more challenging than many other Mediterranean regions – ideal for those who want to experience real, powerful sailing.
The ideal time for a sailing trip in the Cyclades is May and June as well as September and October. These months are characterized by pleasant temperatures, stable weather conditions and good sailing conditions with moderate Meltemi.
From mid-July to the end of August, the Meltemi can be very strong to extreme. This period is particularly suitable for guests who appreciate an intense, windy sailing experience.
Arrival is via Santorini International Airport (JTR). Alternatively, it is possible to travel via Athens (ATH) by domestic flight or ferry. The respective port of embarkation can be reached from Santorini Airport in a short time.
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 neighbors – 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 harbor 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.
A sailing trip through the Cyclades is not a gentle glide, but an area with personality. Clear air, strong winds, wide horizons and striking coastlines characterize the experience. Between active stages, quiet anchorages and impressive shore excursions, the result is a journey that combines nature, culture and a genuine sailing experience.
Discover our sailing trips through the Aegean Sea
stylish, authentic, unforgettable
The Meltemi blows strongly, especially in midsummer, and can become very strong between mid-July and the end of August. In spring and fall, it is usually more moderate and pleasant.
The Cyclades are particularly suitable for guests who are looking for a windier, sportier area and enjoy longer stages.
The sailing trips usually start and end on Santorini. Mostly off the island of Vlichada.
Yes – in true Sailing Classics style, the wind determines the course. The route can be flexibly adapted to enjoy the best sailing conditions and most beautiful bays. Authentic sailing is our focus, not a rigid timetable.
Yes, the Ionian Islands offer numerous sheltered bays, beaches and charming harbors that are regularly visited.
A lot is already prepared for you on board – towels, shampoo and usually also sun protection products are available. For your summer sailing vacation, we recommend light, comfortable clothing, sturdy shoes for shore excursions, swimwear, possibly a windbreaker and a sun hat. It is best to travel with soft travel bags, as they are easier to stow in the cabins and offer more space than suitcases.
Our cabins are comfortable and well-designed, with a wardrobe, shelves and storage space under the beds. There is plenty of space for the duration of the trip, and foldable travel bags are the best option instead of hard-shell suitcases.
Discover our special offers for solo travelers in the Caribbean:
🎉Christmas & New Year’s Eve without single cabin supplement
🏝️Bis 31.03.2026: half single cabin supplement on all Caribbean voyages
⛵Tip: Combine two weeks and secure a multi-week discount
