experiences

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

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

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

4.9

Super!

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

Duration:

7 days - 7 nights

Greece:

Cyclades

12 travellers

€826

€870

Per person

4.9

Super!

Athens to Paros: the best of the Western Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€713

€750

Per person

Autumn Gems of Cyclades away from the crowds on 51 ft yacht

Duration:

7 days - 7 nights

Greece:

Cyclades

2 travellers

€580

Per person

4.9

Super!

Da Milos a Paros: il meglio delle Cicladi

Duration:

7 days - 7 nights

Greece:

Cyclades

8 travellers

€800

Per person

5.0

Super!

From Milos to Mykonos

Duration:

7 days - 7 nights

Greece:

Cyclades

8 travellers

€550

Per person

Why book a holiday with Sailsquare?

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

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

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 - Private yacht sailing holidays with skipper in the Cyclades

39 reviews

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.

Sailing in the Cyclades

10/14/2024

Marine C.

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

Sailing in the Cyclades

10/8/2024

Sofia P.

Switzerland

An overall amazing experience! Thank you Yann!

Mykonos and Serifos: the mythical Cyclades on a luxury sailboat with chef

09/29/2024

David H.

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!

Customer Support

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

Call us at

+44 2035144220

Read our

Contact & Support

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!