experiences

4.9

Super!

Mykonos to Athens by Fast Cruise

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

4.8

Super!

Paros, Serifos, Kytnos, the fantastic Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€790

€711

Per person

5.0

Super!

Paros-Naxos and Small Cyclades

Greece: Cyclades

5 days - 5 nights

One departure available

September

€900

Per person

5.0

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

September - October

€1,080

Per person

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

Greece: Cyclades

7 days - 7 nights

One departure available

October

€580

Per person

4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

October

€897

€807

Per person

4.0

Sailing the Small Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

September - October

Starting from

€789

€710

Per person

5.0

Exclusive boat, you choose the route and the Cyclades islands to see!

Greece: Cyclades

6 days - 7 nights

2 departures available

September - October

€833

Per person

4.6

Una vera navigazione con uno skipper oceanico

Greece: Cyclades

7 days - 7 nights

One departure available

September - October

€750

Per person

Unique Cyclades sailing holiday with Hostess

Greece: Cyclades

7 days - 7 nights

One departure available

September - October

€994

€795

Per person

Tour by schooner to discover Antiparos - Despotiko - Blue Lagoon

Greece: Cyclades

1 day - 0 nights

29 departures available

September - October

Starting from

€115

Per person

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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

70 reviews

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

09/15/2025

Florian H.

Germany

Great trip & great skipper!

Sailing in the Cyclades

09/9/2025

Jana H.

Germany

Our very first sailing trip turned out to be an unforgettable great experience! Great boat, interesting excursions, delicious food, and most importantly with skipper Yann the dearest and most caring person you could wish for! We like to remember all the experiences (including the card games that were new to us) and all your unexpected surprises on a boat. A big thank you (unfortunately without blue flip-flops 😉) Jana and Flo

Sailing in the Cyclades

09/9/2025

Giovanni P.

Italy

Great!

Fast cruising Cicladi Occidentali

09/8/2025

Beatrice D.

Netherlands

Annalisa and Lorenzo welcomed me on their boat and made me feel at home from day one. They made me discover the beauty of the Cyclades with its crystal clear waters and magical sunsets. They filled the days with their stories and delicious food! It was an unforgettable holiday and I will definitely come back for another trip with them!

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