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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!

127

experiences

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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

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

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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+6 travellers

have booked

Starting from

€1,796

€1,890

Per person

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5.0

From Kos to Athens via the Dodecanese, the Sporades and the Cyclades

Duration:

9 days - 10 nights

Greece:

Dodecanese

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+7 travellers

have booked

€890

Per person

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4.9

Fast cruising Cicladi Occidentali

Duration:

6 days - 7 nights

Greece:

Cyclades

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+6 travellers

have booked

Starting from

€960

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

Give this experience a try!

Starting from

€1,500

Per person

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4.9

Small Cyclades

Duration:

6 days - 7 nights

Greece:

Cyclades

Give this experience a try!

Starting from

€890

Per person

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4.9

Paros and the fantastic Small Cyclades

Duration:

6 days - 7 nights

Greece:

Cyclades

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+26 travellers

have booked

€950

Per person

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4.9

Kufner 54 the alternative to the catamaran in the Dodecanese - WITH HOSTESS

Duration:

6 days - 7 nights

Greece:

Dodecanese

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+6 travellers

have booked

€1,000

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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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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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

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

1544 reviews

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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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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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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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