header cover
logo

Log in

Private yacht sailing holidays with skipper in the Cyclades

Visiting the Cyclades islands by hiring a sailboat will be one of the most beautiful experiences you can do. Choose between sailing, catamaran and gulet and let yourself be conquered by the contrast of the blue and white of Mykonos, Santorini, Paros and the Little Cyclades.

cover image
avatar image

4.8

Super!

Athens to Paros: the best of the Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August - September

€950

Per person

cover image
avatar image

5.0

Super!

From Piraeus to Mykonos: the Aegean by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

June

€1,000

Per person

cover image
avatar image

5.0

Super!

Sailing in the Aegean, the sea of the Gods!

Greece: Cyclades

7 days - 7 nights

One departure available

May

€500

Per person

cover image
avatar image

4.9

Super!

Fast Sailing Experience between Authentic Islands and Good Food

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

cover image
avatar image

4.8

Super!

Paros Serifos Kytnos the fantastic Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August

€950

Per person

cover image
avatar image

4.9

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

9 departures available

May - October

Starting from

€1,080

Per person

cover image
avatar image

5.0

Super!

From Mykonos to Athens by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

Per person

cover image
avatar image

4.8

Super!

From Ios to Milos, the best of the Central Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€750

Per person

cover image
avatar image

5.0

Super!

Sailing Odyssey in the heart of Cyclades

Greece: Cyclades

6 days - 6 nights

One departure available

September

€1,100

€990

Per person

cover image
avatar image

4.8

Super!

Milos to Paros: the best of the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

July - August

€900

Per person

cover image
avatar image

5.0

Super!

Mykonos and the Western Cyclades by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

4 departures available

July - September

Starting from

€1,000

€900

Per person

cover image
avatar image

4.8

Super!

Luxury catamaran cruise in the Cyclades

Greece: Cyclades

7 days - 7 nights

20 departures available

May - November

Starting from

€1,000

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

77 reviews

avatar image

Sailing in the Cyclades

04/22/2026

Miguel M.

-

Spain

Exceptional experience!! Yann is a skipper who knows the navigation area and the most suitable anchorages and ports well. In addition to being an excellent sailor, he is an endearing person who seeks the well-being of his "crew", carrying out activities on land such as hikes or visits to interesting places that give added value. His boat "[hidden]" is a sailboat of the highest level, very comfortable and designed to sail in extreme conditions and therefore absolutely safe. Yann keeps it in pristine condition and is spotlessly clean. In short, it is a highly recommended experience.

Sailing in the Cyclades

10/12/2025

Lisa B.

-

Germany

Yann has a great and modern boat and always surprised us with culinary delights - whether on board or ashore. The excursions and activities were very varied and we enjoyed the tavern visits very much. Linguistically, it was not always easy for us in the group, as almost all the others in the group, like Yann, were native speakers of French or knew the language and then often switched to French in group situations with each other, where we felt left out and often had the feeling that we didn't notice the plans. That was a bit of a shame. Yann is an experienced skipper, we always felt safe - he knows the Cyclades very well and we were able to explore great bays and places. However, we caught a week with quite strong winds, which brought us as beginners to some limits (seasick) - we personally would not have had the ambition to cover such long distances under these circumstances. All in all, we had an intense adventure, which we remember with many highlights. :) thank you

Milos to Paros: the best of the Cyclades

09/27/2025

Rocco G.

-

Switzerland

Alessandro is a legend, an excellent cook and tries to fulfill customer requests in the best way always taking into consideration the safety and comfort of the crew. You feel like you care about delivering the best experience possible. We had bad luck with the weather, but despite this it was an adventurous and nice week.

From Paros to Milos, the hidden gems of Cyclades

09/24/2025

Anna B.

-

Germany

The best sailing trip we could have wished for. Nikos knows the waters and his boat by heart. Even with weather changes he brought us to the sweetest spots of the Cyclades. Besides his technical skills he is a fun and welcoming skipper that considers the wishes of the crew at all times.

Customer Support

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!

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!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964