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Sailboat yacht sailing holidays & tours in Greece

Discover more than 87 opportunities to get on board a Sailboat adventure in Greece. 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

11 departures available

July - 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

9 departures available

July - 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

6 departures available

July - November

Starting from

€650

€618

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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4.9

Super!

Fast cruising Cicladi Occidentali

Greece: Cyclades

6 days - 7 nights

2 departures available

August - September

Starting from

€955

Per person

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5.0

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

7 departures available

August - October

Starting from

€1,080

Per person

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4.8

Super!

Come and discover the Saronic Islands from Poros

Greece: Saronic Islands and Athens area

6 days - 6 nights

6 departures available

July - October

Starting from

€585

€497

Per person

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4.8

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

7 departures available

July - September

Starting from

€600

€540

Per person

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4.9

Super!

From Kos to Rhodes: the beautiful south Dodecanese

Greece: Dodecanese

7 days - 7 nights

One departure available

July

€800

Per person

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4.9

Super!

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

Greece: Cyclades

7 days - 7 nights

One departure available

September

€870

Per person

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5.0

Super!

The enchantment of the sea: the Dodecanese islands

Greece: Dodecanese

7 days - 7 nights

2 departures available

September

Starting from

€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 - Sailboat yacht sailing holidays & tours in Greece

1642 reviews

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From Rhodes to Kos: the fantastic South Dodecanese

07/1/2025

Patrizia F.

-

Italy

Andare in barca con Alessio e Anna è stata una delizia , baie splendide , Alessio sempre molto attento a capire i posti dove fermarsi e come accontentare tutti nei limiti del possibile. Anna deliziosa e preziosa con la sua instancabile energia. Consiglio di provare !
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

06/30/2025

Gilberto B.

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Italy

Alessandro, Carlo, Andrea e Marta sono andati oltre ogni possibile aspettativa regalandoci una settimane di relax, incantevoli spot nello ionico, deliziosi pranzi a bordo e fuori. Abbiamo trovato disponibilità, sensibilità e accoglienza fuori dal comune. Barca pulita, ottima comunicazione e organizzazione. Nessun dettaglio lasciato al caso, una vacanza indimenticabile!
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From Rhodes to Kos: the fantastic South Dodecanese

06/30/2025

Silvia A.

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Italy

Bellissima esperienza oltre ogni aspettativa. Lo skipper super disponibile e simpatico e i luoghi visitati di una bellezza autentica hanno reso questa vacanza ,insieme alle altre persone che erano con me , davvero indimenticabile ❤️ Grazie di cuore
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From the Dodecanese to the Cyclades: sailing off the beaten track!

06/30/2025

elisabetta m.

-

Italy

Andrea è un professionista, sempre pronto a renderti felice! Abbiamo visitato posti stupendi e in condizioni di vento e mare piuttosto impegnative, che solo un esperto marinaio poteva rendere cosi' piacevoli!

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