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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

1752 reviews

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Corfù Paxos Antipaxos

06/16/2025

Marie Claude H.

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France

Nous avons passé une semaine merveilleuse pour notre première expérience d’une semaine sur un voilier. Stefania et Giovanni sont des hôtes d’exception. Très accueillants, nous nous sommes tout de suite sentis comme à la maison. Stefania est une remarquable cuisinière, très attentionnée à nous faire découvrir la cuisine grecque. Tout est frais et fait maison ! Giovanni est toujours à l écoute pour nous faire découvrir des sites exceptionnels et loin de la foule touristique. Le bateau est très confortable. Nous avons partagé plein de moments authentiques. Nous sommes prêts à revenir très vite ! Nous recommandons fortement cette croisière aussi bien pour la gentillesse et compétence de nos hôtes que pour la beauté des lieux où nous nous sommes rendus . Chaque jour était un nouveau paradis. 1000 mercis!
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Fast sailing holiday in the Cyclades with gourmet cuisine on board

06/15/2025

Alberto L.

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Italy

Un Sogno a Vela Indimenticabile con Lorenzo e Annalisa Se cercate un'esperienza in barca a vela perfetta tra le Cicladi, scegliete Lorenzo e Annalisa. Per una settimana, ci hanno guidato da Lavrio a Mykonos, esplorando le Piccole Cicladi, e siamo rimasti entusiasti. La loro conoscenza delle isole è eccezionale, permettendoci di scoprire angoli di paradiso e condizioni di navigazione ideali. A bordo, l'atmosfera è sempre stata rilassata e accogliente. Da segnalare la cucina veramente deliziosa e variegata!! . La loro sinergia crea un ambiente sereno e piacevole. Le Piccole Cicladi ci hanno regalato paesaggi mozzafiato, e grazie a loro abbiamo vissuto appieno ogni momento: bagni in baie deserte e cene in taverne tipiche. Lorenzo e Annalisa sono compagni di viaggio appassionati ed esperti. Hanno superato ogni aspettativa, trasformando una vacanza in un'avventura straordinaria. Li raccomandiamo vivamente a chiunque desideri un'esperienza autentica e indimenticabile tra le isole greche.
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Cyclades and Microcyclades with a magnificent 15-meter boat

06/15/2025

Ester L.

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Italy

La nostra esperienza in barca con Fabio è stata straordinaria! Nonostante fosse la nostra prima volta in barca a vela ci siamo sentiti subito a casa e a nostro agio. La barca è accogliente ed ha tutti i comfort, e i pasti che abbiamo fatto a bordo hanno avuto i panorami più belli e irripetibili che si possano immaginare. Fabio ci ha insegnato e raccontato molto della vita in mare, ed è stato per noi un arricchimento e un'ispirazione per ripetere questa bellissima esperienza anche in futuro. I luoghi che abbiamo visto sono incantevoli, inoltre Fabio li conosce tutti molto bene e ci ha fatto da guida (anche gastronomica!). Non potremmo consigliare esperienza migliore! Sarà bellissimo anche per neofiti!!
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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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