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Yacht sailing holidays & skippered tours in Greece

Discover more than 33 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

33

experiences

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4.9

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Duration:

6 days - 6 nights

Greece:

Ionian Islands

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+26 travellers

Have booked

Starting from

€680

Per person

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5.0

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Duration:

6 days - 6 nights

Greece:

Ionian Islands

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+7 travellers

Have booked

Starting from

€550

Per person

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5.0

The enchantment of the sea: Lefkada, Ithaca, Kefalonia and the smaller islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

Be the first one to book!

Starting from

€480

Per person

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Antiparos Discovery Schooner Tour - Despotiko - Blue Lagoon

Duration:

1 day - 0 nights

Greece:

Cyclades

Be the first one to book!

€130

Per person

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4.7

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

Duration:

6 days - 7 nights

Greece:

Cyclades

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+2 travellers

Have booked

€1,900

€2,000

Per person

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4.7

Best local sailing experience on 50ft monohull away from the crowds

Duration:

6 days - 7 nights

Greece:

Cyclades

Be the first one to book!

€893

€940

Per person

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4.9

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

Duration:

6 days - 7 nights

Greece:

Cyclades

Be the first one to book!

€760

€800

Per person

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4.9

From Corfu sailing between turquoise sea and white beaches - hostess on board

Duration:

6 days - 7 nights

Greece:

Ionian Islands

Be the first one to book!

Starting from

€810

Per person

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5.0

A dream sailing from Kos to Rhodes

Duration:

5 days - 6 nights

Greece:

Dodecanese

Be the first one to book!

€900

Per person

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4.8

Gone with the Wind: 2 boats in Corfu and the Ionian Islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

Be the first one to book!

€647

Per person

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4.8

Gone with the Wind: 2 boats in Corfu and the Ionian islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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+14 travellers

Have booked

Starting from

€647

Per person

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4.8

Sailing cruise in the Greek islands - The Saronic Islands

Duration:

7 days - 7 nights

Greece:

Saronic Islands and Athens area

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+21 travellers

Have booked

€618

€650

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 - Yacht sailing holidays & skippered tours in Greece

1542 reviews

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Sailing course in the Cyclades

10/18/2023

Antoine B.

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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!
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SHARE & SAIL: explore Cyclades with new friends

10/10/2023

Monica F.

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

10/8/2023

Umberto B.

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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!
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LAST MINUTE! - The secrets of the small Dodecanese islands between history and culture

10/8/2023

Christoph R.

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Germany

Wir sind zu zweit mit Emanuel und Annalisa eine Woche durch den Dodekanes gefahren und es war ein phantastisches Erlebnis. Die beiden haben uns so herzlich und liebevoll aufgenommen und uns die schönsten Seiten der Inseln und auch ihre nicht so bekannten Seiten gezeigt. Von kleinen Fischerdörfern über verwunschene Bergdörfer bis zu einsamen Buchten zum Übernachten war alles dabei, was das Herz begehrt. Beim Schnorcheln haben wir Tintenfische, Zackenbarsche und Skorpionfische gesehen und einmal hat uns sogar eine Seeschildkröte besucht. Emanuels Grillkünste sind der Hammer und wir haben eine schöne Mischung zwischen originalen Restaurants und an Bord Küche gehabt. Und das Segeln im Revier ist wunderschön - mit dem weißen Boot durchs tiefblaue Wasser zu fahren bleibt unvergesslich. Und die beiden haben einen prima Weg gefunden, uns behutsam ins Segelhandwerk einzuführen. Es war ein herrlicher Urlaub und fühlte sich an, wie mit guten Freunden unterwegs zu sein. Danke dafür !!

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