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Yacht sailing holidays & skippered tours in Greece

Discover more than 23 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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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

2 departures available

October

Starting from

€550

Per person

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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

2 departures available

October

Starting from

€550

Per person

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4.9

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

October - November

Starting from

€650

€618

Per person

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5.0

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

3 departures available

September - October

Starting from

€1,080

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

3 departures available

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!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

€750

€713

Per person

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5.0

Super!

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

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

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4.5

SHARE & SAIL - 6 days Exploring & Relaxing at the heart of Cyclades

Greece: Cyclades

6 days - 6 nights

2 departures available

October

€790

Per person

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4.3

Premium

ATHENS Dream Premium - All Inclusive Catamaran Cruise with Stewardess

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

October

Starting from

€1,260

Per person - min 2 pax

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Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

October

Starting from

€997

€798

Per person

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4.7

Premium

Big and luxurious 60ft catamaran in Saronic - best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

3 departures available

October

Starting from

€2,100

€1,995

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

1748 reviews

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

06/11/2025

Gemma M.

-

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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Sail from Milos to Mykonos with a Beneteau 50 experience the Cyclades

06/7/2025

Denis P.

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Italy

Splendida settimana tra le Cicladi… Gianfranco é davvero un grande capitano, che oltre alle doti nautiche sa anche coinvolgerti nella navigazione e farti sentire subito a tuo agio a bordo… La barca poi… Splendida! L’unico problema é il dover sbarcare al termine della vacanza… Grazie Gianfranco!
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Corfu to Athens via the exciting Corinth Canal

06/7/2025

Irene A.

-

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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Sail from Milos to Mykonos with a Beneteau 50 experience the Cyclades

06/6/2025

Alessandra C.

-

United States

Esperienza meravigliosa! Gianfranco è uno skipper fantastico, simpatico e dalle mille risorse, ci ha fatto vedere posti bellissimi navigando sempre in sicurezza. La [hidden] è spaziosa e confortevole, una splendida barca! Le Cicladi sono isole meravigliose con acqua cristallina, delfini, tartarughe, cibo delizioso e magici paesini da visitare. Vacanza assolutamente raccomandata!

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