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Yacht sailing holidays & skippered tours in Greece

Discover more than 36 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

36

experiences

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7 Day Greek Sailing Adventure - Dodecanese Islands

Duration:

7 days - 6 nights

Greece:

Dodecanese

Be the first one to book!

€1,653

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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5.0

Explore the charms of Greece aboard our sailboat

Duration:

6 days - 6 nights

Greece:

Ionian Islands

Be the first one to book!

€700

Per person

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The sailing adventure of your summer

Duration:

6 days - 6 nights

Greece:

Dodecanese

Be the first one to book!

€1,450

Per person

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4.8

Discover the Ionian Islands, Lefkada, Meganisi, Kalamos, Atokos and Itaque

Duration:

6 days - 6 nights

Greece:

Ionian Islands

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+8 travellers

Have booked

€585

Per person

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Sporades Islands: sailing holidays are more than just holidays!

Duration:

7 days - 7 nights

Greece:

Sporades

Be the first one to book!

Starting from

€830

Per person

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5.0

100% women's sailing cruise

Duration:

6 days - 7 nights

Greece:

Cyclades

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+3 travellers

Have booked

€860

Per person

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4.6

Cruise to the Ionian Islands, Ithaca and Zakynthos on a luxury boat with chef

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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+18 travellers

Have booked

Starting from

€1,200

Per person

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4.9

Sailing holiday among the wonders of the Cyclades from Athens

Duration:

6 days - 7 nights

Greece:

Cyclades

Be the first one to book!

€810

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

€670

Per person

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4.9

Cyclades and Microcyclades with a magnificent 15-meter boat

Duration:

6 days - 7 nights

Greece:

Cyclades

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+4 travellers

Have booked

Starting from

€750

Per person

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5.0

From Milos to Mykonos

Duration:

6 days - 7 nights

Greece:

Cyclades

Be the first one to book!

€550

Per person

Why book a holiday with Sailsquare?

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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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