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Yacht sailing holidays & skippered tours in Greece

Discover more than 28 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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4.8

Super!

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

Greece: Ionian Islands

7 days - 7 nights

One departure available

June - July

Starting from

€600

€540

Per person

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5.0

Super!

Treat yourself to an unforgettable holiday. Embark with us in Kos

Greece: Dodecanese

7 days - 6 nights

One departure available

June - July

Starting from

€800

€720

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

One departure available

June - July

Starting from

€1,100

€1,045

Per person

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3.7

Adventure around Lefkada, Khefalonia, Ithaca and Zakynthos

Greece: Ionian Islands

6 days - 6 nights

One departure available

June - July

Starting from

€300

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

One departure available

June

€790

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

One departure available

June - July

Starting from

€2,100

€1,995

Per person

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4.3

Premium

Cruise to discover Corfu and Ionian Greece - Hostess & Half Board

Greece: Ionian Islands

7 days - 7 nights

2 departures available

June - July

Starting from

€835

€752

Per person - min 2 pax

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4.9

One way from the Cyclades to the Dodecanese on a magnificent 15-meter boat

Greece: Cyclades

7 days - 7 nights

One departure available

June

€700

Per person - min 2 pax

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5.0

Sailing holiday with yoga and SUP in the Saronic islands

Greece: Saronic Islands and Athens area

6 days - 7 nights

One departure available

June - July

Starting from

€990

Per person

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4.3

In the Sea of Ulysses among the most beautiful islands

Greece: Ionian Islands

6 days - 7 nights

2 departures available

June - July

Starting from

€800

€720

Per person

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Discovering the Dodecanese from KOS

Greece: Dodecanese

7 days - 7 nights

One departure available

June

€1,300

€1,150

Per person

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5.0

Corfù Paxos Antipaxos

Greece: Ionian Islands

6 days - 6 nights

One departure available

June - July

Starting from

€900

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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