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Crewed yacht sailing holidays & tours in Cyclades

Discover more than 15 opportunities to get on board a Crewed adventure in Cyclades. A unique experience with a local skipper, starting at €350 a week.

15

experiences

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4.7

Premium

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

Duration:

6 days - 7 nights

Greece:

Cyclades

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31 travellers

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Starting from

€2,090

€2,200

Per person

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4.9

Super!

From Paros to Mykonos

Duration:

6 days - 7 nights

Greece:

Cyclades

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4 travellers

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€835

Per person

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4.6

The Cyclades with Serifos and Mykonos on a dream boat with chef

Duration:

7 days - 7 nights

Greece:

Cyclades

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3 travellers

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€1,400

Per person

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4.9

Super!

Mykonos to Athens by Fast Cruise

Duration:

6 days - 7 nights

Greece:

Cyclades

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6 travellers

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€835

Per person

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4.9

Super!

Small Cyclades

Duration:

6 days - 7 nights

Greece:

Cyclades

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23 travellers

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Starting from

€955

Per person

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4.9

Super!

Baie and fast sailing from Milos to Paros

Duration:

6 days - 7 nights

Greece:

Cyclades

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6 travellers

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Starting from

€1,070

Per person

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4.9

Super!

Sailing holiday among the wonders of the Cyclades from Athens

Duration:

6 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€780

Per person

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4.9

Super!

Fast sailing in the Cyclades from Paros to Milos

Duration:

6 days - 7 nights

Greece:

Cyclades

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6 travellers

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€1,160

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board from Mykonos to Santorini

Duration:

7 days - 6 nights

Greece:

Cyclades

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6 travellers

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€1,050

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board from Kos to Santorini

Duration:

7 days - 6 nights

Greece:

Cyclades

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6 travellers

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€1,050

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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2 travellers

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€700

Per person

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4.9

Super!

Milos and other Cycladic pearls with hostess on board

Duration:

7 days - 7 nights

Greece:

Cyclades

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2 travellers

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€750

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 - Crewed yacht sailing holidays & tours in Cyclades

48 reviews

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Small Cyclades

09/14/2024

Stefan E.

-

Switzerland

Annalisa and Lorenzo are wonderful hosts and very skillful skippers. We had an amazing time with delicious food, visiting beautiful spots, swimming at peaceful hidden islands. The whole planning is flawless, given us a very relaxing trip and memorable first sailing experience. Grazie mille =D
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Best local sailing experience on 50ft monohull away from the crowds

09/9/2024

Nicola F.

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Italy

Perfetta organizzazione della vacanza da parte di Aga. Abbiamo navigato e scoperto le piccole Cicladi, partecipando progressivamente alle manovre compiute dallo skipper. Cucina favolosa da parte di Aga a colazione e pranzo, mentre la sera era prevista una cena in un ristorante dell'isola appena raggiunta. Compagni di viaggio super, vacanza indimenticabile.
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Small Cyclades

08/26/2024

EMANUELE P.

-

Italy

Tutto perfetto! Annalisa e Lorenzo sono bravissimi ed offrono un servizio unico. Assolutamente da provare!
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Big and luxurious 60ft catamaran in Cyclades - best local experience with hostess

08/25/2024

Rolf S.

-

Switzerland

Es war alles super Ich persönlich wäre gerne noch mehr gesegelt….

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