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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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Reviews - Yacht sailing holidays & skippered tours in the Cyclades

424 reviews

Sailing in the Aegean, the sea of the Gods!

06/1/2026

Viviana C.

A tour full of adventure! Andrea is very professional and with his experience he made us discover these wonderful islands, in all their beauty.

Sailing in the Aegean, the sea of the Gods!

05/31/2026

James W.

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IT

Everything about this experience was 5 star! Andrea is an incredible professional who knows how to curate the perfect tour. If given the chance, we would absolutely sail with him again!
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Sailing in the Aegean, the sea of the Gods!

05/25/2026

Massimo O.

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IT

Andrea is exquisite and knows how to put you at ease. He is prepared and able to solve the various unforeseen events typical of life at sea. The variable weather prevented us from making the most of the experience at sea but the alternative proposals for shore excursions proposed by Andrea were equally exhaustive.
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Sailing in the Cyclades

04/22/2026

Miguel M.

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ES

Exceptional experience!! Yann is a skipper who knows the navigation area and the most suitable anchorages and ports well. In addition to being an excellent sailor, he is an endearing person who seeks the well-being of his "crew", carrying out activities on land such as hikes or visits to interesting places that give added value. His boat "[hidden]" is a sailboat of the highest level, very comfortable and designed to sail in extreme conditions and therefore absolutely safe. Yann keeps it in pristine condition and is spotlessly clean. In short, it is a highly recommended experience.

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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

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