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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!

68

experiences

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5.0

Super!

SECRET DODECANESE: at full roadstead with skipper and kitchen

Duration:

6 days - 6 nights

Greece:

Dodecanese

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+9 travellers

have booked

€1,300

Per person

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The PIG Project: a Pirate in the Greece story

Duration:

7 days - 6 nights

Greece:

Cyclades

Give this experience a try!

€1,500

Per person

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7 Day Greek Sailing Adventure - Dodecanese Islands - All inclusive

Duration:

7 days - 6 nights

Greece:

Dodecanese

Give this experience a try!

€1,653

Per person

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5.0

Super!

Sailing cruise in the Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

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+16 travellers

have booked

€850

Per person

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4.9

Super!

Da Milos a Paros: il meglio delle Cicladi

Duration:

7 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€790

Per person

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4.9

Super!

Paros and the fantastic Small Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

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+31 travellers

have booked

€950

Per person

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4.9

Super!

Milos, Kimolos, Poliegos, Folegandros, the fantastic Western Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

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+8 travellers

have booked

€800

Per person

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4.6

A real sail between beautiful islands in the comfort of a catamaran

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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+2 travellers

have booked

€750

Per person

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5.0

Super!

Cyclades: Relaxation and Excitement on a Sailing Boat from Athens

Duration:

7 days - 6 nights

Greece:

Cyclades

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+30 travellers

have booked

Starting from

€900

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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+10 travellers

have booked

Starting from

€1,796

Per person

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The sailing adventure of your summer - Steward on board

Duration:

7 days - 6 nights

Greece:

Dodecanese

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+4 travellers

have booked

Starting from

€1,450

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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+40 travellers

have booked

€1,590

Per person

Why book a holiday with Sailsquare?

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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

1588 reviews

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

07/26/2024

Michele N.

-

Italy

Esperienza super, vele spiegate appena il vento permetteva.. Andrea fantastico capitano e disponibile a far partecipare l'equipaggio alle manovre quando possibile. Non serve commentare le diverse sole, ovviamente fantastiche.. Esperienza assolutamente consigliata
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Sailing cruise in the Greek islands - The Saronic Islands

07/25/2024

Janne M.

-

Finland

5 star experience!
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Cyclades: Relaxation and Excitement on a Sailing Boat from Athens

07/24/2024

Letizia G.

-

Switzerland

Serenità per rallentare, calma per riposare, tempo per ascoltare, incontri inaspettati, amicizie inattese, emozioni che nutrono, fragilità messe a nudo, inconfessate paure, anime in disordine, parole che curano, silenzi per rispondersi. Isole da esplorare, poetici scorci, affettuosi abitanti, bagni per rinascere, colori dimenticati, musica negli elementi, raffiche di felicità, meraviglia improvvisa, lo straordinario nell' ordinario condiviso. Filippo conosce il mare come pochi hanno potuto conoscerlo e l' arte del navigare che richiede contemporaneamente rigore e intuizione, prudenza e audacia, umiltà e ostinazione,. Con pazienza, empatia e professionalità ha spalancato a mio figlio la porta di un mondo a lui sconosciuto e sorprendente, quello dell'andar per mare al ritmo della natura (ormai indelebile nella sua giovane memoria). Consiglio: portate i bimbi a bordo di questa splendida esperienza (meglio se in coppia con un compagno) e fate loro un regalo importante. Perché preziosi e rari sono i viaggi di cui si avverte nostalgia ancora prima che siano terminati.
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Wandering through the Ionian Islands

07/22/2024

Giuseppe A.

-

France

We had a great vacation week with Giorgio and his great crew around Lefkada. Giorgio’s boat is very confortable with plenty of space and Giorgio knows very well the nicest spots for swimmîng and visiting the villages on the Greel coast.

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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

Greece: departures by month

Other travel ideas

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