experiences

4.9

Super!

Paros, Serifos, Kytnos, the fantastic Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€711

€790

Per person

4.9

Super!

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

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€891

€990

Per person

4.9

Super!

From Santorini to Milos: the fantastic Cyclades of the South

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€810

€900

Per person

4.6

Sailing in the most beautiful Saronic with chefs: Hydra and Spetses

Duration:

6 days - 6 nights

Greece:

Saronic Islands and Athens area

2 travellers

have left

Starting from

€1,235

€1,300

Per person

4.9

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Duration:

7 days - 7 nights

Greece:

Saronic Islands and Athens area

61 travellers

have left

Starting from

€618

€650

Per person

4.9

Super!

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

Duration:

7 days - 7 nights

Greece:

Cyclades

12 travellers

have left

€826

€870

Per person

4.9

Super!

From Samos to Kos: the best of the North Dodecanese

Duration:

7 days - 7 nights

Greece:

Dodecanese

Give this experience a try!

Starting from

€713

€750

Per person

4.9

Super!

From Kos to Rhodes: the beautiful south Dodecanese

Duration:

7 days - 7 nights

Greece:

Dodecanese

Give this experience a try!

Starting from

€760

€800

Per person

4.9

Super!

From Rhodes to Kos: the fantastic South Dodecanese

Duration:

7 days - 7 nights

Greece:

Dodecanese

Give this experience a try!

Starting from

€760

€800

Per person

4.9

Super!

From Kos to Samos: the perfect Dodecanese

Duration:

7 days - 7 nights

Greece:

Dodecanese

Give this experience a try!

Starting from

€760

€800

Per person

4.9

Super!

Athens to Paros: the best of the Western Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€713

€750

Per person

4.9

Super!

The fantastic Saronic Islands and the surroundings of Athens

Duration:

7 days - 7 nights

Greece:

Saronic Islands and Athens area

22 travellers

have left

Starting from

€646

€680

Per person

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 - Yacht sailing holidays & skippered tours in Greece

1732 reviews

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.

Sailing cruise in the Greek islands - The Saronic Islands

11/3/2024

Stefano B.

Italy

Grazie a Bertrand per avermi fatto fare una settimana memorabile in barca a vela , posti stupendi clima perfetto Grazie

Sailing cruise in the Greek islands - The Saronic Islands

11/2/2024

Elie R.

France

Super semaine ! Bertrand est expert de la région et nous a emmenés à des endroits magnifiques en s'adaptant aux conditions météo et aux capacités et envies de l'équipage. Le bateau est très confortable, il y a même l'eau chaude ! Merci captain Jack et à une prochaine on espère !

Sailing paradise in Greece on a big 50 ft boat: the best local experience

10/30/2024

Santiago D.

Colombia

A unique and spectacular experience! I sailed for a week and I loved it! Highlights: we sailed every day, the breakfast and lunches were incredible (we all asked for the recipes) and at night we went out to eat at typical restaurants on the Greek islands. I hope to return soon!

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!

Call us at

+44 2035144220

Read our

Contact & Support

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!