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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!

107

experiences

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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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+26 travellers

have booked

Starting from

€550

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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+15 travellers

have booked

Starting from

€750

Per person

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5.0

Sailing Cyclades

Duration:

6 days - 7 nights

Greece:

Cyclades

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+98 travellers

have booked

Starting from

€920

Per person

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5.0

Sailing from Rhodes to Kos

Duration:

6 days - 7 nights

Greece:

Dodecanese

Give this experience a try!

€650

Per person

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5.0

Sail from Kos to Kos heading North

Duration:

6 days - 7 nights

Greece:

Dodecanese

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+30 travellers

have booked

Starting from

€750

Per person

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5.0

Corfù Paxos Antipaxos

Duration:

6 days - 5 nights

Greece:

Ionian Islands

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+4 travellers

have booked

€850

Per person

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5.0

Didactic week on a sailing boat - Ionian Greece

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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+3 travellers

have booked

€1,172

€1,250

Per person

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4.9

Sailing in the Saronic Islands with hostess on board

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

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+4 travellers

have booked

€745

Per person

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4.8

Gunwale in the water and off to the 38^ Brindisi Corfu

Duration:

8 days - 8 nights

Greece:

Ionian Islands

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Stefano C.

has booked

€450

€500

Per person

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4.7

Big and luxurious 60ft catamaran in Saronic, the best local experience

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

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+10 travellers

have booked

Starting from

€1,499

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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+38 travellers

have booked

Starting from

€680

Per person

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5.0

Sailing in the Northern Dodecanese from Kos to Samos

Duration:

6 days - 7 nights

Greece:

Dodecanese

Give this experience a try!

€650

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

1546 reviews

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The fantastic Saronic Islands and the surroundings of Athens

05/21/2024

Steve T.

-

Canada

My family and I spent a week onboard with Alessandro exploring the Saronic Islands. We were taken to some amazing places that I will remember forever. Some were busy with people and tourists and some were completely ours - just the bay and our boat. This was a trip of a lifetime with a great skipper!
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Orthodox Easter in Greece in the Saronic Islands

05/14/2024

Albert P.

-

Spain

Una experiencia inolvidable con Pierluigi y Nicoletta. No solo disfrutarás de las playas y el mar, sino que vivirás una inmersión cultural y gastronómica en el lugar de destino. A pesar de ir con un grupo exclusivamente de italianos, me hicieron sentir uno más del grupo y la barrera lingüística no fue ningún problema, ya que dominan el inglés e incluso el español. Lo repetiría mil veces. Si tienes dudas, ¡no te lo pienses!
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Sailing cruise in the Greek islands - The Saronic Islands

04/28/2024

ERIC V.

-

France

Pour la seconde fois, j’ai pris énormément de plaisir à naviguer avec Bertrand autour des îles Saroniques. Cette fois ci nous avons poussé jusque Nauplie, situé à l’Ouest du Peloponeise, dans le Golf Argolique. Émettant le désir de faire une navigation de nuit, Bertrand n’a pas hésité à adapter l’´itinéraire pour répondre à ma demande.
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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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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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