Homepage cover
logo

Log in

Sailboat yacht sailing holidays & tours in Cyclades

Discover more than 9 opportunities to get on board a Sailboat adventure in Cyclades. A unique experience with a local skipper, starting at €350 a week.

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 - Sailboat yacht sailing holidays & tours in Cyclades

416 reviews

Ios, Sikinos, Folegandros and Anafi: the fantastic Cyclades of the South

09/9/2026

Elisabetta M.

-

BE

WONDERFUL: this word can give you an idea of what awaits you on a holiday like this. It was an unforgettable week, in the middle of the sea, with fantastic people I didn't know and an absolutely unique skipper! Alessandro is the skipper that everyone would like, punctual, a profound connoisseur of the sea, an excellent cook and an unforgettable storyteller! We were lulled by the sea, we ate delicious food and, last but not least, the comets kept us company! I would leave immediately... thanks also to my extraordinary travel companions!
avatar image

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

09/2/2026

Rafaela C.

-

IT

First experience on a sailing boat: a nice adventure with some ideas for improvement Since this is my first time on a sailing boat, the final balance is certainly positive. It was an enriching experience and the group turned out to be very pleasant, although there are some aspects that could make the trip even more comfortable and inclusive for the participants. Value of experience and galley management: The overall cost was a bit high compared to the services included. ( at the time of booking it must be specified that in addition to the initial expense there are other expenses, this has not been specified. For example.. fuel, water supply galley starter pack..... this is specified only once you have booked) Being at the first experience, we would have liked to have had extra support from the skipper or in any case from the organizational group at the time of the initial expense: a little advice to optimize the galley and avoid the superfluous (perhaps buying the rest gradually in the ports) would have been really useful. ( example once the excel has been filled in, the organizers with more experience than us can remove what seems extra to them ... instead of "scolding" each other because we did our own thing. Involvement in maneuvers: It is good to warn and know that it is an active holiday: even without any previous experience, you get involved and there is an absolute need to help the skipper during maneuvers and navigation, which makes you feel part of the crew but you need to be educated just in case. Group and fleet dynamics: Over half of the group already knew each other, and for those who struggle a little more to integrate or leave alone, this can create a small initial obstacle. To facilitate friendships, it would be great if the organization included more moments of sharing between the three boats, perhaps supporting them during the afternoon stops and not just the two evenings of sharing to really make the experience live as one big group. A trip that leaves a good memory and that I would do again, with the hope that these suggestions can help the organization to make the experience even more welcoming for future participants.

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

08/27/2026

FRANCESCO P.

-

IT

Unfortunately due to Meltemi we had to totally change the initial itinerary by falling back on the Saronic islands, consequently we did not see the Cyclades at all. Apart from this inconvenience all good!
avatar image

Ios, Santorini, Anafi: the breath of the Cyclades

08/26/2026

Chiara Q.

-

IT

Alessio is a very prepared, kind and helpful skipper. Wonderful and very comfortable boat, and the sea-islands of the Cyclades are a real enchantment! Beautiful experience, I recommend!

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