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Sailboat yacht sailing holidays & tours in Cyclades

Discover more than 56 opportunities to get on board a Sailboat adventure in Cyclades. A unique experience with a local skipper, starting at €350 a week.

56

experiences

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4.7

Great sailing from Athens to Mykonos in the Cyclades

Duration:

6 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€621

€690

Per person

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4.7

Mykonos, the delightful little Cyclades and magical Santorini

Duration:

6 days - 7 nights

Greece:

Cyclades

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4 travellers

€666

€740

Per person

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4.9

Super!

Paros, Serifos, Kytnos, the fantastic Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€711

€790

Per person

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4.9

Super!

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

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€891

€990

Per person

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4.9

Super!

From Santorini to Milos: the fantastic Cyclades of the South

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€810

€900

Per person

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4.9

Super!

Cyclades on a sailing boat: adventure with comfort!

Duration:

7 days - 7 nights

Greece:

Cyclades

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6 travellers

€665

€700

Per person

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4.7

Premium

Best local sailing experience on 50ft monohull away from the crowds

Duration:

6 days - 7 nights

Greece:

Cyclades

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73 travellers

Starting from

€1,140

€1,200

Per person

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5.0

Super!

From Ithaca to Milos, we will sail between the Cyclades islands

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€599

€630

Per person

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5.0

Super!

Sail from Milos to Mykonos with a Beneteau 50 experience the Cyclades

Duration:

6 days - 6 nights

Greece:

Cyclades

Give this experience a try!

€618

€650

Per person

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5.0

Super!

The gems of the Cyclades: Mykonos, Iraklia, Schinoussa, Koufonisi, Naxos

Duration:

6 days - 6 nights

Greece:

Cyclades

Give this experience a try!

€665

€700

Per person

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5.0

Super!

Treat yourself to a unique holiday: From Mykonos, Small Cyclades, to Kos

Duration:

6 days - 6 nights

Greece:

Cyclades

Give this experience a try!

€684

€720

Per person

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4.9

Super!

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

Duration:

7 days - 7 nights

Greece:

Cyclades

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12 travellers

€826

€870

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

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 - Sailboat yacht sailing holidays & tours in Cyclades

347 reviews

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Sailing in the Cyclades

11/3/2024

Aaron S.

Amazing skipper, all the stops were fun the food was great and the overall atmosphere on the boat for the week was fantastic.
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Sailing in the Cyclades

10/14/2024

Marine C.

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Switzerland

Cette semaine de voile dans les Cyclades fut un enchantement permanent. Yann est un excellent skipper, à l’écoute de chacun, d’une grande gentillesse et générosité. Il aime partager sa passion et son amour pour la Grèce et c’est ce qui rend cette croisière unique. Son bateau est très confortable et sûr, avec des équipements haut de gamme. Enfin, chaque île découverte regorge de richesses incroyables, que ce soit des petites criques où nous étions seuls au monde, ou bien des magnifiques villages et délicieuses tavernas dont Yann connaît toutes les bonnes adresses! Il est certain que je remonterai à bord de Korto un jour! Kenavo Yann
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Sailing in the Cyclades

10/8/2024

Sofia P.

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Switzerland

An overall amazing experience! Thank you Yann!
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Mykonos and Serifos: the mythical Cyclades on a luxury sailboat with chef

09/29/2024

David H.

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United States

Had a wonderful time sailing with Renato and Luciana on their 54 Jenneau sail boat "Lulu"! The boat is very comfortable and sea kindly and Renato is an expert captain and "Lulu" a fantastic chef meals onboard were delishious! They know the best ports harbors and bays for swimming and sightseeing ashore. It was a great vacation plus sailing vacation very highly recommended and would definitely go again!

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