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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

Premium

Big and luxurious 60ft catamaran in Cyclades - best local experience with hostess

Greece: Cyclades

6 days - 7 nights

One departure available

August

€2,947

€2,800

Per person

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4.9

Super!

Two weeks in flotilla between the Cyclades and the Peloponnese

Greece: Cyclades

13 days - 14 nights

One departure available

August

€2,050

Per person

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4.9

Super!

Fast cruising Cicladi Occidentali

Greece: Cyclades

6 days - 7 nights

2 departures available

August - September

Starting from

€955

Per person

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5.0

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

7 departures available

August - October

Starting from

€1,080

Per person

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4.9

Super!

A week in the flotilla in the Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,050

Per person

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4.9

Super!

Milos, Kimolos, Poliegos, Folegandros, the fantastic Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€870

Per person

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5.0

Super!

We will depart from Kos to head to Mykonos with a very comfortable boat

Greece: Cyclades

7 days - 6 nights

One departure available

September

€750

Per person

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4.9

Super!

Astypalaia, Anafi and Santorini: the pearls of the Southern Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August

€990

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

September

€955

Per person

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4.9

Super!

From Paros to Mykonos

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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4.9

Super!

Mykonos to Athens by Fast Cruise

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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4.9

Super!

Paros, Serifos, Kytnos, the fantastic Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€790

€711

Per person

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Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Yacht sailing holidays & skippered tours in the Cyclades

385 reviews

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One way from the Cyclades to the Dodecanese on a magnificent 15-meter boat

06/29/2025

Gabriele A.

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Italy

Bella esperienza in ottima compagnia. Fabio, lo skipper, un vero lupo di mare, ed Irene dolcissima presenza. Abbiamo visitato diverse isole come da programma ed oltre. Un'esperienza da rivivere, in semplicità e leggerezza, com'è stato in questa vacanza. Buon vento! Gabriele & Barbie gymnastic
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Secret Aegean with skipper and kitchen on board from Santorini to Kos

06/26/2025

Melissa C.

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Italy

Settimana in barca a vela tra Santorini, Anafi, Astypalea, Nisyros e Kos – una vacanza vera, di quelle che ti restano addosso. Annalisa ed Emmanuel, i nostri skipper, sono stati incredibili: super preparati, ma anche accoglienti e alla mano. Ci hanno trattati come re e regine fin dal primo giorno, con una cura e una gentilezza che raramente si trovano. Anche quando il vento ci ha regalato una sosta più lunga su un’isola, hanno saputo trasformare tutto in un’occasione per scoprire posti bellissimi, fare esperienze nuove e mangiare in locali autentici dove si spende poco e si mangia davvero da dio. Anche a bordo si mangia benissimo: cucinano tutto loro, con prodotti locali freschi, e si vede che ci mettono passione. Non sono solo bravi skipper, sono anche ottimi cuochi! Ogni pasto era delizioso! Abbiamo fatto di tutto: trekking, bagni nelle sorgenti calde, visita alla caldera di un vulcano, e spesso dormivamo in baie tranquille ed isolate, sotto un cielo pieno di stelle. Una pace incredibile. Si naviga quasi sempre a vela facendoci partecipare alle manovre e spiegandoci tutto con pazienza e passione. Non è la solita vacanza all-inclusive, è un’esperienza diversa, più autentica e libera – e proprio per questo è speciale. È mare vero, natura, libertà, semplicità. Se cercate qualcosa di autentico, lontano dal caos e pieno di bellezza, ve la straconsiglio.
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We cross the Aegean: Milos, Small Cyclades, Amorgos, Astypalea

06/25/2025

Anna M.

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Luxembourg

Andrea is an extremely skillful skipper, he knows exactly how to make you feel comfortable on the boat, he worries about your needs and is always ready to answer questions and curiosities. Our destinations were amazing and magic Greece just makes the rest. Highly recommended!
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Secret Aegean with skipper and kitchen on board from Santorini to Kos

06/24/2025

gina c.

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United States

The skippers are experienced sailors who care about safety + weather conditions and maintain a very clean, comfortable boat down to the smallest details. They were kind enough to help me maneuver a heavy piece of luggage which I'm super grateful for. I booked solo and extremely last minute without knowing the right questions to ask, and I do recommend conversing prior to get a feel of fit for this type of trip. I could have benefited from discussing my dietary preferences and restrictions in comparison to the group, especially given that the food is purchased and prepared by the skippers without the option of purchasing/ cooking your own. It also didn't occur to me to inquire about allotted water consumption per passenger, and in our case a swift shower wasn't possible each day whether on board or in marina. If you decide to embark, know that you are in experienced hands who will carefully anticipate weather restrictions and modify as needed, and you definitely won't be shopping or cooking. Thank you!

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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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