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Yacht sailing holidays & skippered tours in the Cyclades

Discover the treasures of the Aegean Sea - a collection of islands with their own unique charm, landscapes, and coastlines. The Cycladic Islands act as a brilliant destination to unwind, relax, and connect with some of the most stunning natural beauty. Explore the stunning Santorini, Mykonos, and Ios with a passionate, local skipper.

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4.7

Luxury catamaran cruise in the Cyclades

Greece: Cyclades

7 days - 7 nights

4 departures available

September - November

€1,000

Per person

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4.9

Super!

Cyclades from Milos to Milos

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person - min 2 pax

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5.0

Super!

From Mykonos to Athens by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

€760

Per person

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5.0

Super!

From Milos to Mykonos by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September

€1,000

€750

Per person

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5.0

Super!

Mykonos and the Western Cyclades by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

2 departures available

September

Starting from

€1,000

€750

Per person

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4.9

Super!

7 giorni a vela alle Cicladi con gran finale a Santorini

Greece: Cyclades

6 days - 7 nights

One departure available

August - September

€790

Per person

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4.9

Super!

Baie and fast sailing from Milos to Paros

Greece: Cyclades

6 days - 7 nights

One departure available

September

€940

Per person

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4.9

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

October

Starting from

€950

Per person

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4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,290

€1,161

Per person

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5.0

Sailing Odyssey in the heart of Cyclades

Greece: Cyclades

6 days - 6 nights

One departure available

September

€990

Per person

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4.0

Sailing & Diving in the Small Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,390

€1,251

Per person

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4.6

Cabin boarding in the Cyclades, Astypalea and Santorini, sailing 17m. with chef

Greece: Cyclades

7 days - 7 nights

One departure available

August - September

€1,400

Per person

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Reviews - Yacht sailing holidays & skippered tours in the Cyclades

450 reviews

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

08/27/2026

FRANCESCO P.

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IT

Unfortunately due to Meltemi we had to totally change the initial itinerary by falling back on the Saronic islands, consequently we did not see the Cyclades at all. Apart from this inconvenience all good!
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Ios, Santorini, Anafi: the breath of the Cyclades

08/26/2026

Chiara Q.

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IT

Alessio is a very prepared, kind and helpful skipper. Wonderful and very comfortable boat, and the sea-islands of the Cyclades are a real enchantment! Beautiful experience, I recommend!

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

08/25/2026

Eleonora A.

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IT

Wonderful holiday thanks to the Skipper Massimo, extremely prepared and professional and a crew of wonderful people with whom I was lucky enough to spend unique moments. The boat was in very good condition and spacious.

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

08/25/2026

Niccolò C.

-

IT

Awesome experience! Top boat and skipper, the evenings organized were always very well managed and followed the mood of the holiday

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8 reasons to choose the Cyclades for your next sailing holiday:

  • Home to some of the most spectacular beauty in the Greek Isles in Santorini, Mykonos, and Ios
  • Lesser-known treasures of the Cyclades such as Sifnos, Koufonisia, and Amorgos which are regarded by expert skippers as some of the most perfect Greek islands
  • An ideal climate for sailing from April through to October
  • Learn the special sirtaki dance in the area’s street festivals
  • Taste the popular Greek liquor, ouzo, with a meal of local produce
  • Discover some of the world’s most charming coves and lagoons
  • Immerse yourself in the regions iconic white, cubic architecture and charming fishing villages

The best places & specific destinations to visit during your sailing holidays in the Cyclades:

Sailing the world renowned landscapes of Mykonos

This island of Mykonos, a favourite holidaying spot, is recognised for the beauty of its hilly landscapes, sandy beaches, and picturesque Cycladic white country chapels. Where as, the crescent-shaped Santorini, or Thira, as it’s otherwise known, is in fact a group of islands in the southern Cyclades.

The volcanic complex of the Santorini Islands has crafted some of the most unique arrangements of rock and ocean - while sunset images from the famous Caldera have become synonymous with romance. Then there is the island of Ios, known as Nios by the locals, and considered by many as one of the most beautiful islands in the Cyclades. The Panayia Gremiótissa church that stands at the highest point of Ios offers a striking view over the town and out onto the open sea.

Exploring the secret beauty of the Cyclades

The best kept secrets of the Cyclades are the islands of Sifnos, Koufonisia, and Amorgos. Sifnos with its red bougainvillea that hugs the white of the buildings, as the gentle Meltemi breeze flows over the hills and onto coastline. Koufonisa is said to compete with the best of Greek islands on all fronts. The port of Koufonisa sits on the islands only village, here some of the most charming blue lagoons are being secluded. Amorgos rises dramatically from the Aegean, creating extremely unique landscapes, and is described by skippers as a charm that you most confront at least once in your life.

The Cyclades, which originates from the Greek word for ring or circle, is in fact made up of around 220 different islands. This variety in island, partnered with the Meltemi winds, make for some of the best conditions for a sailing holiday full of discovery and fun.

Tips to help you to better plan for your next sailing holidays in the Cyclades:

  • As the region boasts a warm climate for much of the year, sailing the Cyclades is recommended between early April and late October.
  • You can find experiences for a week in the Cyclades with a skipper from €500 per person. This figure excludes transport to and from the holiday. It is important to remember that depending on the month of travel and style of boat pricing is subject to change.
  • The two main airports in the area are based in Mykonos and Santorini. If not clear in the holiday listing, reach out to a holiday’s organising skipper to understand more precisely the most suitable transport options.

The best sailing holiday itineraries for your next adventure in the Cyclades with a skipper:

  • Due to the Cyclades having approximately 220 islands, there are a great number of different sailing holiday itinerary options. Popular itineraries include the exploration of some of the areas most popular islands including - Sifnos, Poliegos, Kimolos, Milos, Paros, Syros, Santorini, and Mykonos.
  • Such concentration of different islands means that some skippers like to propose visiting a new island each day. If there are shorter holiday time frames available, there are many itineraries that revolve more heavily on the Small (otherwise known as Little, Minor or Lesser) Cyclades.

Cyclades: the best travel ideas

Other travel ideas

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