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Crewed yacht sailing holidays & tours in Greece

Get on board on a crewed sailing holiday in Greece for the most relaxed time ever.

39

experiences

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Salt, Earth and Sun: yoga retreat on a catamaran with hostess (Full Board) 

Duration:

7 days - 7 nights

Greece:

North Egean Islands

Starting from

€1,855

Per person

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4.9

A week exploring the Dodecanese

Duration:

6 days - 7 nights

Greece:

Dodecanese

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+8 travellers

have booked

€930

Per person

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4.9

Athens to Lefkada via the Corinth Canal - Stewardess on board

Duration:

7 days - 7 nights

Greece:

Saronic Islands and Athens area

Give this experience a try!

€745

Per person

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5.0

SECRET DODECANESE: Astypalea and Tylos with skipper and kitchen

Duration:

6 days - 6 nights

Greece:

Dodecanese

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+4 travellers

have booked

Starting from

€750

Per person

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4.9

Full sail in the blue of Ionian Greece with hostess on board

Duration:

6 days - 7 nights

Greece:

Ionian Islands

Give this experience a try!

€800

Per person

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4.9

Fine Dodecanese to Samos with a fast-cruiser boat

Duration:

6 days - 7 nights

Greece:

Dodecanese

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+2 travellers

have booked

€930

Per person

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5.0

The Dodecanese: 10 Days, 9 Islands, A Luxurious and Fast Boat

Duration:

10 days - 10 nights

Greece:

Dodecanese

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+2 travellers

have booked

€1,341

€1,490

Per person

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5.0

The perfect island-hopping in Greece! Skipper & Hostess - All included

Duration:

6 days - 6 nights

Greece:

Saronic Islands and Athens area

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+36 travellers

have booked

Starting from

€1,511

€1,590

Per person

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4.9

From Samos to the Small Cyclades by sailboat

Duration:

6 days - 7 nights

Greece:

Cyclades

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+2 travellers

have booked

€960

Per person

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4.6

Unique experience through the Corinth Canal, from the Ionians to Athens

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

Give this experience a try!

€1,045

€1,100

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

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+22 travellers

have booked

Starting from

€893

€940

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

Starting from

€1,796

€1,890

Per person

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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 - Crewed yacht sailing holidays & tours in Greece

144 reviews

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Lefkas and the southern islands, sailing between poetry and myth. Hostess on board.

10/5/2023

Rossella C.

Hansel è una persona davvero disponibile...e molto pacata, che sa amalgamare bene anche equipaggi molto variegati. Ha sicuramente fatto del suo meglio per metterci a nostro agio e farci godere al meglio la vacanza. Un consiglio: dal momento che è molto disponibile anche ad assecondare i desideri della sua ciurma, valutate se studiare il posto che visiterete, in modo da decidere insieme...eventuali cambi di rotta!
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Ready to set sail? Magical places await you! - HOSTESSES on board

09/28/2023

Cathrin K.

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Germany

Umgeben von einem so wunderschönen Meer mit kristallklarem Wasser und außergewöhnlichen Stränden war es eine Woche der totalen Entspannung und magischen Momenten. Es war eine mega Erfahrung mit großartigen Menschen an Bord ... unbeschreiblich. Ich hätte mir keine besseren Crew-Begleiter wünschen können. Unsere Gastgeber Andrea und Noemi waren so fürsorglich, sodass der Törn ein perfektes Erlebnis wurde. Und erst der kleine Mathi (Mathias) ... wir hatten alle wirklich amüsante Momente mit ihm. Andrea ist ein erfahrener Skipper, er kennt die Reiseroute sicher wie kein anderer. Seinen kulinarischen Empfehlungen sind wir gern gefolgt. Großes Dankeschön auch an Allesandro und Carlo, die uns immer auf einem anderen Boot begleitet haben. Diese Tour ist perfekt geeignet, um Ruhe und Entspannung zu finden. Aufgrund eines Schadens am Rudergerät war es leider nicht möglich, zu unsem Highlight die "Blue Lagoon" zu segeln. Schade, dass hier keine andere alternative Möglichkeit angeboten wurde.
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Sailing in the footsteps of Ulysses: 7 days in the Ionian Islands with Hostess on board

09/25/2023

James F.

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United Kingdom

Stefano was an excellent skipper and highly experienced and plotted a great route. Alessia was a brilliant host and between the two of them they made an amazing experience. The boat is large in good condition and comfortable. The food that they made us was just amazing and beyond our expectations. I have been on a few sailing holidays like this but this was the best experience I have had.
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Ready to set sail? Magical places await you! - HOSTESSES on board

09/24/2023

Marie G.

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France

Les bleus sublimes de la mer, les plages d'exception, la nature luxuriante.... Tout y était ! D'autre part, vivre une semaine à bord, avec des personnes d'autres cultures, d'autres langues, c'est vraiment une belle expérience ! Et puis il y a eu nos hôtes, Andrea et Noemi, qui sont d'une telle gentillesse, qui ont à coeur de nous offrir un séjour parfait... Le professionnalisme d'Andrea est remarquable, très sécurisant et ses conseils sont excellents pour choisir les restaurants du soir. Un grand merci pour tant de merveilleux souvenirs ????

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