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Crewed yacht sailing holidays & tours in Greece

Get on board on a crewed sailing holiday in Greece for the most relaxed time ever.

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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

9 departures available

July - October

Starting from

€550

Per person

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4.9

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

11 departures available

July - October

Starting from

€550

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board from Kos to Rhodes

Greece: Dodecanese

7 days - 6 nights

One departure available

September

€1,050

Per person

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5.0

Super!

Corfu and the Ionian Islands

Greece: Ionian Islands

6 days - 7 nights

2 departures available

July

€790

Per person

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4.7

Premium

Big and luxurious 60ft catamaran in Cyclades - best local experience with hostess

Greece: Cyclades

6 days - 7 nights

One departure available

August

€2,947

€2,800

Per person

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4.9

Super!

Fast cruising Cicladi Occidentali

Greece: Cyclades

6 days - 7 nights

One departure available

August - September

€955

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

2 departures available

August - September

Starting from

€955

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board from Santorini to Kos

Greece: Cyclades

7 days - 6 nights

One departure available

September

€1,050

Per person

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4.9

Super!

From Paros to Mykonos

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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4.7

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

11 departures available

June - October

Starting from

€1,100

€1,045

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board - Rhodes to Kos

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

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4.9

Super!

Mykonos to Athens by Fast Cruise

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

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 - Crewed yacht sailing holidays & tours in Greece

184 reviews

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Pack your suitcase and we'll take care of the rest!! Stewards on board!

06/15/2025

Diego D.

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Austria

FANTASTICA! Vacanza splendida all’insegna del relax e del divertimento. Itinerario ben studiato e spiagge da cartolina. Alessandro è uno skipper giovane, capace, molto cortese e sempre disponibile. Anche grazie a lui e all’instancabile steward Carlo, l’atmosfera a bordo è sempre stata piacevole e scherzosa. CONSIGLIATISSIMA!
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

06/11/2025

Gemma M.

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Italy

Un soggiorno meraviglioso reso speciale da Andrea e Marta, due persone splendide che ci hanno fatti sentire subito a casa. La barca è bellissima, curata e in perfette condizioni. Andrea, skipper esperto e sempre disponibile, ci ha accompagnati con il gommone alla scoperta dei luoghi più belli e nascosti, lasciandoci sempre liberi di scegliere il ritmo della giornata. Marta, cuoca eccezionale, ha preparato piatti deliziosi e ha mantenuto la barca sempre pulita e in ordine con una discrezione e una dedizione davvero ammirabili. La compagnia di Matthias, cane dolce e affettuoso, è stata un piacevole valore aggiunto. Un’esperienza davvero unica.
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Corfu to Athens via the exciting Corinth Canal

06/7/2025

Irene A.

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Italy

Bellissima esperienza. Enrica e Omar sono due persone esperte di vela e con una grande attenzione agli ospiti. Abbiamo visitato una Grecia inedita e in ogni momento abbiamo condiviso esperienze e bellissime sensazioni. Consiglio a tutti un viaggio con loro per una vacanza dove avventura, comfort e mare si coniugano in modo naturale e divertente. Grazie Enrica e Omar. Sarò sicuramente vostra ospite di nuovo!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

05/18/2025

Emma K.

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Germany

Ich hatte eine sehr schöne Zeit. Alessandro und Carolina waren sehr nett und haben uns trotz ein paar Tagen Regen gut versorgt. Und sie haben die Route spontan an die Wetterlage angepasst. Einfach top Erfahrung. Danke!

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