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Yacht sailing holidays & skippered tours in Greece

Discover more than 50 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

50

experiences

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Antiparos Discovery Schooner Tour - Despotiko - Blue Lagoon

Duration:

1 day - 0 nights

Greece:

Cyclades

Give this experience a try!

€130

Per person

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7 Day Greek Sailing Adventure - Dodecanese Islands

Duration:

7 days - 6 nights

Greece:

Dodecanese

Give this experience a try!

€1,653

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

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+12 travellers

have booked

€1,050

Per person

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The sailing adventure of your summer

Duration:

6 days - 6 nights

Greece:

Dodecanese

Give this experience a try!

€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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+12 travellers

have booked

€585

Per person

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5.0

Cyclades: Relaxation and Excitement on a Sailing Boat from Athens

Duration:

7 days - 6 nights

Greece:

Cyclades

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+9 travellers

have booked

Starting from

€855

€900

Per person

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Sporades Islands: sailing holidays are more than just holidays!

Duration:

7 days - 7 nights

Greece:

Sporades

Give this experience a try!

Starting from

€860

Per person

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4.9

Fast sailing in the Cyclades from Paros to Milos

Duration:

6 days - 7 nights

Greece:

Cyclades

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+4 travellers

have booked

€1,130

Per person

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5.0

Cyclades and Small Cyclades

Duration:

6 days - 7 nights

Greece:

Cyclades

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+4 travellers

have booked

€1,190

Per person

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4.6

Cruise in the Dodecanese and off the coast of Turkey on a 17m boat with chef

Duration:

6 days - 7 nights

Greece:

Dodecanese

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+6 travellers

have booked

Starting from

€1,400

Per person

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Relaxation in the Ionian islands on a catamaran

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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+3 travellers

have booked

Starting from

€1,000

Per person

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4.7

Wandering among the Ionian islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

Give this experience a try!

€850

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

1543 reviews

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Sailing Cyclades

04/15/2024

yannis b.

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France

Séjour incroyable avec Yann ! Très attentif, drôle et chill dans toutes les situations, dans un bateau très confortable !
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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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