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Yacht sailing holidays & skippered tours in Greece

The Greek Archipelago has over 16,000 km of coastline, with many beaches that run for kilometres, a host of secluded bays and coves, and a rich variety of wildlife. Some say the best sailing waters in the world can be found in Greece!

130

experiences

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5.0

Sailing Cyclades

Duration:

6 days - 7 nights

Greece:

Cyclades

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+81 travellers

have booked

Starting from

€920

Per person

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4.8

Long weekend in Corfu

Duration:

3 days - 3 nights

Greece:

Ionian Islands

Give this experience a try!

€390

Per person

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Sailing on April 25 on a sailboat to the Ionian Islands

Duration:

4 days - 3 nights

Greece:

Ionian Islands

Give this experience a try!

€300

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

Sailing cruise in the Greek islands - The Saronic Islands

Duration:

7 days - 7 nights

Greece:

Saronic Islands and Athens area

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+28 travellers

have booked

Starting from

€523

€550

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

€510

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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+9 travellers

have booked

Starting from

€510

Per person

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5.0

Spring in Sailing during the Orthodox Easter festivities

Duration:

6 days - 7 nights

Greece:

Ionian Islands

Give this experience a try!

€550

Per person

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Sailing to the island of Delos

Duration:

4 days - 3 nights

Greece:

Cyclades

Give this experience a try!

Starting from

€594

€625

Per person

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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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5.0

Orthodox Easter in Greece in the Saronic Islands

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

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+6 travellers

have booked

€500

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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+16 travellers

have booked

€585

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 - Yacht sailing holidays & skippered tours in Greece

1543 reviews

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Sailing Cyclades

04/15/2024

yannis b.

-

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.

-

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.

-

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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Guides & tips


Greece

Ionian Islands, Cyclades Islands and Dodecanese are just some of the most beautiful destinations for a sailing or catamaran vacation in Greece
Guide to Greece by sailboat

Ionian Islands

Paxos, Zakynthos, Kefalonia and Lefkada are just some of the best destinations for a sailing or catamaran vacation in the Ionian Islands.
Guide to Ionian Islands by sailboat

Cyclades islands

Sandy beaches, small bays and blue and white villages have made the Cyclades a world-famous landscape, perfect for exploring by sailboat or catamaran.
Guide to Cyclades islands by sailboat

Greece: the most beautiful places to sail

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