header cover

Crewed yacht sailing holidays & tours in Cyclades

Discover more than 9 opportunities to get on board a Crewed 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

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 - Crewed yacht sailing holidays & tours in Cyclades

42 reviews

avatar image

From Kos to SANTORINI and IOS to discover all the Cyclades with a luxury boat - hostess/chef on board


Antonio M.

Esperienza unica, con due professionisti del mare. La vacanza a vela riserva sempre tante avventure e a differenza di tante altre esperienze si basa molto sulla sensibilità dello skipper a definire il programma giornaliero sulla base delle previsioni meteo. Renato, con la sua vastissima esperienza, è riuscito a tirare fuori il meglio dalla settimana, facendoci esplorare posti straordinariamente belli. Lulú ha condito il tutto con lo stile e la cura dei dettagli, deliziandoci con la sua ottima cucina. La barca è stupenda, pulitissima e affidabile! Consigliatissimi.
avatar placeholder

We cross the Aegean from Athens to Mikonos and Kos: the most beautiful Cyclades - Hostess Chef on board


Frédéric B.



++wild bays visited ++food on the boat boat ++beautiful, ++maintained and ++comfortable +treated like private guests -not like paying customers -every act (wake up, breakfast, swimming, changing back to dry clothes, smoking..) was strictly timed. Without ANY obvious reason (plenty of time to sail to the next point) -6 sailing days booked. In total only 3 hours on sail, the rest on motor (no wind when we were out) & 2 days spent in harbors because the wind could be too strong. No effort made when noticed that we could have have (sportively) sailed. Frustrating to see sailing boats offshore while being on a beach/village -communication rather existent. When R. feels challenged by a question, he overreacts (Ex: by leaving the commands of the boat to us because we dared to ask if we could use sails instead of motor OR by calling us "new rich people" when we asked for the final count for the EUR 400 pp for the current expenses.) -age 48?!? -no instruction -feeling to be at the wrong place -------- SKIPPER ANSWER ------------- Dear Frederic, We are sorry that your first boat experience did not meet your expectations. On the boat there are rules to be respected regarding smoking (unthinkable to smoke while sailing and in the cabin!), order and cleanliness so that everyone is comfortable. The itinerary you have chosen (From Athens to Kos) is an adventurous choice for those who love to travel many miles. Unfortunately the wind cannot be booked and when it is too strong for safety reasons we stop. Sailing cannot be learned in a week and neither can education. Leave the cabin in the shameful condition in which you left it (literally throw away sheets) and then ask for the final report, which, as you were told, can be consulted at any time and available to everyone (with receipts and invoices) on the table from correspondence, two days after finishing the cruise, it is incomprehensible. It was not a pleasant experience for us.
avatar placeholder

One-way cruise from Paros to Lavrio (Athens)


Simone B.


United Kingdom

We had an amazing trip around the Cyclades with Lorenzo and Annalisa. They were super caring with all our needs, showed us wonderful places, and served us delicious food. We would recommend and will definitely be doing it again.
avatar placeholder

Small Cyclades from Paros (Koufonissi, Amorgos, Schinoussa, Paros)


Isa B.



Annalisa et Lorenzo sont des professionnels de la navigation de la cuisine et du savoir vivre. A la fois chaleureux et très présents à la manoeuvre comme en cuisine, pour nous servir et nous informer, nos hôtes ont su s'éclipser par moment et laisser le groupe profiter. Choix de mouillages idylliques loin de tout avec toujours un point d'intérêt inattendu et singulier à voir à terre. Bateau vraiment performant et parfaitement entretenu. Barré de mains de maitre par Annalisa Attention toutefois la croisière ne peut offrir plus que le confort d'un monocoque. douches rapides sur le pont, un sanitaire marin pour 6. Grazie Mille Annalisa e Lorenzo e sicuramente a presto

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

MastercardVisaAmerican ExpressApple pay

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