header cover

Monohull yacht sailing holidays & tours in Cyclades

Discover more than 28 opportunities to get on board a Monohull adventure in Cyclades. A unique experience with a local skipper, starting at €350 a week.

28

experiences

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 - Monohull yacht sailing holidays & tours in Cyclades

308 reviews

avatar image

Sailing course in the Cyclades

10/18/2023

Antoine B.

-

Belgium

Superbe semaine avec Sylvain. Skipper professionnelle qui vous mets a l'aise et vous explique tout. Il vous emmène a des magnifiques mouillages et nous avons descendu les petites cyclades rapidement. Le bateau est très confortable et très chouette a naviguer même quand le vent est au dessus des 30 nœuds. Je vous recommandes Sylvain pour votre prochaine aventure!
avatar placeholder

SHARE & SAIL: explore Cyclades with new friends

10/10/2023

Monica F.

-

Australia

We had the absolute best time on our trip and would 100% recommend this to anyone looking to explore the Greek Islands. Orestis was the best skipper, very attentive and knowledgeable and willing to join in on the fun. We had a great crew who were up for the adventure and really loved the sailing aspect along with all the challenges that come with it. If you’re looking for a hands on, real down to earth experience then this would definitely be for you. This trip was the highlight of our time in Greece! Thank you Orestis and George :)
avatar image

Best local experience and amazing views in Cyclades on a big 50 ft boat

10/8/2023

Umberto B.

-

Italy

La gestione della vacanza è stata come indicato nel programma. La barca Zorbas è molto comoda anche per me che sono alto 1.90 e che potevo stare comodamente in piedi nella Dinette e nell’ingresso alla cabina. Abbiamo fatto delle belle navigate a vela partecipando attivamente al cambio vele e agli ormeggi. Le colazioni e i pranzi preparati da Aga erano sempre perfetti. Abbiamo anche fatto una Avventurosa discesa ad una Taverna tipica in una isola disabitata. Compagni di crociera a dir poco fantastici! Insomma…Vacanza molto piacevole e rilassante!
avatar placeholder

Best local experience and amazing views in Cyclades on a big 50 ft boat

09/16/2023

Aude P.

-

Portugal

My daughter and I have had a wonderful experience and enjoyed very much our stay on the boat. Greg have succeed to avoid the bad weather which was happening in Greece by carefully studying and planning our sailing journey without taking away the discovery and the fun. We have experience some real sailing moments with some rough sea which was for me one of the highlight of the trip. The journey took us in some unexpected places and made us discover the beauty of the Cyclades. An other highlight of the stay was the absolutely wonderful lunches and healthy breakfast Aga prepared for us everyday. The relax and friendly atmosphere on board was very pleasant. Overall a fantastic holiday we will never forget.

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

MastercardVisaAmerican ExpressApple pay

© 2023 Sailsquare Srl SB • All rights reserved - VAT IT07860990964