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Sailboat yacht sailing holidays & tours in Cyclades

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

15

experiences

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Chill & Adventure Sailing Greek Islands to Mykonos+DJ, sailing trainer

Duration:

8 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€593

€790

Per person

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4.7

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

Duration:

6 days - 7 nights

Greece:

Cyclades

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+72 travellers

have booked

Starting from

€903

€950

Per person

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5.0

Super!

Sailing in the Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

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+121 travellers

have booked

Starting from

€920

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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+2 travellers

have booked

€810

Per person

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4.9

Super!

From Paros to Mykonos

Duration:

6 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€850

Per person

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5.0

Super!

100% women's sailing cruise

Duration:

7 days - 7 nights

Greece:

Cyclades

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+7 travellers

have booked

€860

Per person

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4.6

EXCLUSIVE CYCLADES on luxury boat

Duration:

7 days - 8 nights

Greece:

Cyclades

Give this experience a try!

€1,050

Per person

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4.9

Super!

Cyclades and Microcyclades with a magnificent 15-meter boat

Duration:

7 days - 7 nights

Greece:

Cyclades

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+34 travellers

have booked

€1,100

Per person

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5.0

Super!

Sailing cruise in the Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

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+16 travellers

have booked

€850

Per person

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4.9

Super!

Da Milos a Paros: il meglio delle Cicladi

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€790

Per person

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4.9

Super!

Paros and the fantastic Small Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

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+31 travellers

have booked

€950

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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+8 travellers

have booked

€800

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

318 reviews

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Cyclades: Relaxation and Excitement on a Sailing Boat from Athens

07/24/2024

Letizia G.

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Switzerland

Serenità per rallentare, calma per riposare, tempo per ascoltare, incontri inaspettati, amicizie inattese, emozioni che nutrono, fragilità messe a nudo, inconfessate paure, anime in disordine, parole che curano, silenzi per rispondersi. Isole da esplorare, poetici scorci, affettuosi abitanti, bagni per rinascere, colori dimenticati, musica negli elementi, raffiche di felicità, meraviglia improvvisa, lo straordinario nell' ordinario condiviso. Filippo conosce il mare come pochi hanno potuto conoscerlo e l' arte del navigare che richiede contemporaneamente rigore e intuizione, prudenza e audacia, umiltà e ostinazione,. Con pazienza, empatia e professionalità ha spalancato a mio figlio la porta di un mondo a lui sconosciuto e sorprendente, quello dell'andar per mare al ritmo della natura (ormai indelebile nella sua giovane memoria). Consiglio: portate i bimbi a bordo di questa splendida esperienza (meglio se in coppia con un compagno) e fate loro un regalo importante. Perché preziosi e rari sono i viaggi di cui si avverte nostalgia ancora prima che siano terminati.
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Sailing in the Cyclades

07/22/2024

Arianna B.

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Belgium

I had a wonderful first sailing experience of my life! Yann is just perfect: attentive to all needs and desires of the crew. he treated us with extraordinary experiences, such as bbq on deserted islands under the moon! he knows very well all the islands. his boat is very comfortable and up to date with. environmentally friendly technologies, which is an important added plus. I highly recommend him for your next sailing, enjoy!
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Cyclades and Microcyclades with a magnificent 15-meter boat

07/13/2024

Simone C.

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Italy

Esperienza bellissima, con Fabio ci si sente al sicuro con ogni mare. La barca è stupenda. In giro tra le piccole cicladi abbiamo toccato baie approdi e porticcioli indimenticabili, avendo la possibilità di fare anche qualche giro a terra, potendo dire così di aver conosciuto un pochino l'isola. Cercheremo di ripetere
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Cyclades: Relaxation and Excitement on a Sailing Boat from Athens

07/12/2024

Heike S.

-

Italy

Il vento decide dove si può navigare! Le isole scelte dallo Skipper erano molto belle ed è stato molto rilassante.

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