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Sailboat yacht sailing holidays & tours in Greece

Discover more than 86 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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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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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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4.9

Super!

Two weeks in flotilla between the Cyclades and the Peloponnese

Greece: Cyclades

13 days - 14 nights

One departure available

August

€2,050

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

9 departures available

June - September

Starting from

€600

€540

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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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

€585

Per person

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4.9

Super!

A week in the flotilla in the Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,050

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!

Fast cruising Cicladi Occidentali

Greece: Cyclades

6 days - 7 nights

One departure available

August - September

€955

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

1629 reviews

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Sailing cruise in the Greek islands - The Saronic Islands

06/23/2025

Catherine H.

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United Kingdom

We had an amazing week sailing around the Saronics. Bertrand has a brilliant knowledge of the area and knew all the best spots for mooring and places to visit. Our favourite moments were when we moored up for the night, swam off the boat and watched the sunsets.....we also enjoyed getting stuck in with sailing activities ... great fun!
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We cross the Aegean: Milos, Small Cyclades, Amorgos, Astypalea

06/19/2025

Elisa L.

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United Kingdom

The trip was great. Andrea is a very experienced skipper and knows all hidden gems of Greece! Every day was full of surprises, including seeing turtles, tuna fishing, and local wine festival. I particularly appreciated Andrea’s attention to the environment and the promotion of a responsible, local and more authentic way of travelling. Highly recommended!
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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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