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

4.7

Premium

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

Greece: Cyclades

6 days - 7 nights

2 departures available

August

Starting from

€2,737

€2,600

Per person

cover image
avatar image

5.0

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

7 departures available

August - October

Starting from

€1,080

Per person

cover image
avatar image

4.9

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

2 departures available

August - September

Starting from

€955

Per person

cover image
avatar image

5.0

Super!

Secret Aegean with skipper and kitchen on board from Santorini to Kos

Greece: Cyclades

7 days - 6 nights

One departure available

September

€1,050

Per person

cover image
avatar image

4.9

Super!

Astypalaia, Anafi and Santorini: the pearls of the Southern Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August

€990

Per person

cover image
avatar image

4.9

Super!

From Paros to Mykonos

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

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

4.9

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

4.9

Super!

Fast cruising Cicladi Occidentali

Greece: Cyclades

6 days - 7 nights

2 departures available

August - September

Starting from

€955

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!

Milos to Paros: the best of the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

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

41 reviews

avatar placeholder

Sail from Milos to Mykonos with a Beneteau 50 experience the Cyclades

06/7/2025

Denis P.

-

Italy

Splendida settimana tra le Cicladi… Gianfranco é davvero un grande capitano, che oltre alle doti nautiche sa anche coinvolgerti nella navigazione e farti sentire subito a tuo agio a bordo… La barca poi… Splendida! L’unico problema é il dover sbarcare al termine della vacanza… Grazie Gianfranco!
avatar image

Sail from Milos to Mykonos with a Beneteau 50 experience the Cyclades

06/6/2025

Alessandra C.

-

United States

Esperienza meravigliosa! Gianfranco è uno skipper fantastico, simpatico e dalle mille risorse, ci ha fatto vedere posti bellissimi navigando sempre in sicurezza. La [hidden] è spaziosa e confortevole, una splendida barca! Le Cicladi sono isole meravigliose con acqua cristallina, delfini, tartarughe, cibo delizioso e magici paesini da visitare. Vacanza assolutamente raccomandata!
avatar image

Sailing in the Cyclades

11/3/2024

Aaron S.

Amazing skipper, all the stops were fun the food was great and the overall atmosphere on the boat for the week was fantastic.
avatar image

Sailing in the Cyclades

10/14/2024

Marine C.

-

Switzerland

Cette semaine de voile dans les Cyclades fut un enchantement permanent. Yann est un excellent skipper, à l’écoute de chacun, d’une grande gentillesse et générosité. Il aime partager sa passion et son amour pour la Grèce et c’est ce qui rend cette croisière unique. Son bateau est très confortable et sûr, avec des équipements haut de gamme. Enfin, chaque île découverte regorge de richesses incroyables, que ce soit des petites criques où nous étions seuls au monde, ou bien des magnifiques villages et délicieuses tavernas dont Yann connaît toutes les bonnes adresses! Il est certain que je remonterai à bord de Korto un jour! Kenavo Yann

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