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Yacht sailing holidays & skippered tours in Greece

Discover more than 48 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

48

experiences

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4.9

Skiathos Skopelos Alonissos and Surroundings The Fantastic Sporades

Duration:

6 days - 7 nights

Greece:

Sporades

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+21 travellers

have booked

€800

Per person

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5.0

The enchantment of the sea: the Dodecanese islands

Duration:

6 days - 7 nights

Greece:

Dodecanese

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+8 travellers

have booked

€750

Per person

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5.0

Lose yourself in the magic of the Southern Ionian Islands

Duration:

7 days - 6 nights

Greece:

Ionian Islands

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+7 travellers

have booked

Starting from

€900

Per person

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5.0

Sailing BenEssere in Ionian Greece

Duration:

6 days - 6 nights

Greece:

Ionian Islands

Give this experience a try!

Starting from

€1,125

€1,250

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

€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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+4 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

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+2 travellers

have booked

€1,100

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

€1,200

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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+4 travellers

have booked

€1,796

€1,890

Per person

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4.7

Wandering through the Ionian Islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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+11 travellers

have booked

€800

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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+28 travellers

have booked

€950

€1,000

Per person

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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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+30 travellers

have booked

Starting from

€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.

-

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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