header cover
sailsquare logo

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

5.0

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

3 departures available

September - October

€1,080

Per person

cover image
avatar image

5.0

Super!

From Paros to Milos, the hidden gems of Cyclades

Greece: Cyclades

5 days - 5 nights

3 departures available

August - September

Starting from

€900

€810

Per person

cover image
avatar image

4.8

Super!

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

Greece: Cyclades

7 days - 7 nights

One departure available

September

€870

Per person

cover image
avatar image

4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

September

€955

Per person

cover image
avatar image

4.9

Super!

Fast cruising Cicladi Occidentali

Greece: Cyclades

6 days - 7 nights

One departure available

August - September

€955

€790

Per person

cover image
avatar image

5.0

Super!

We will depart from Kos to head to Mykonos with a very comfortable boat

Greece: Cyclades

7 days - 6 nights

One departure available

September

€750

Per person

cover image
avatar image

4.9

Super!

Mykonos to Athens by Fast Cruise

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

September

€790

€711

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

September

€800

Per person

cover image
avatar image

5.0

Super!

Paros-Naxos and Small Cyclades

Greece: Cyclades

5 days - 5 nights

2 departures available

September

Starting from

€900

€810

Per person

cover image
avatar image
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

cover image
avatar image

4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

3 departures available

September - October

Starting from

€997

€798

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 - Private yacht sailing holidays with skipper in the Cyclades

61 reviews

avatar image

Small Cyclades

08/18/2025

Franesco B.

-

Italy

An exceptional holiday! Challenging sea conditions but two professionals proceeded impeccably. Together we sailed sublimely, overcoming adversity, finding ourselves immersed in a true and uncontaminated reality. Undoubtedly a recommendable holiday but I always suggest doing it with the mentality of those who want to help a companion (not a skipper), of those who want to savor intense and sincere realities forgetting some secondary comforts. Finally, special mention to the culinary skills of Lorenzo and Annalisa. Super
avatar image

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

08/18/2025

Francesco P.

-

Italy

Amazing adventure holidaying across the most beautiful seas Aga & Greg loving and caring hosts Incredible local vegetarian and healthy food experience on board And tavern selection for the nights on the ground A must try experience!
avatar placeholder

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

08/17/2025

Maxime M.

-

Italy

What a wonderful week with Aga, Greg and the other travellers. Magnificent landscapes of course but also and above all a great crew who made us discover the less touristy places, delighted us with an exceptional cuisine and the boat is beautiful and very comfortable. Only positive. We will be back for sure!
avatar placeholder

From Paros to Milos, the hidden gems of Cyclades

08/16/2025

lorenzo k.

-

Italy

Perfect skipper both from a professional and human point of view. Super recommended

Customer Support

nightLifeGeneralInfo

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!

search

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