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Yacht sailing holidays & skippered tours in Greece

Discover more than 59 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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5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

3 departures available

August - September

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

4 departures available

August - 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

September

Starting from

€650

€618

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

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5.0

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

4 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

4 departures available

August - 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

3 departures available

August - September

Starting from

€600

€540

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

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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!

We will depart from Kos to head to Mykonos with a very comfortable boat

Greece: Cyclades

7 days - 6 nights

One departure available

September

€750

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

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 - Yacht sailing holidays & skippered tours in Greece

1776 reviews

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Pack your suitcase and we'll take care of the rest!! Stewards on board!

07/7/2025

Diana U.

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Italy

Amazing experience! It was my first time on a sailing boat, and it was incredible. We visited beautiful places and beaches. Ale and Carlo are the perfect duo to sail with! Ale is professional, knows everything about sailing and the best beaches, and was always available and super friendly. Carlo was also very kind and helpful. I'm a vegetarian, and he always made something special just for me. Thank you for an unforgettable week! Hope to come back soon! :)
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From the Dodecanese to the Cyclades: sailing off the beaten track!

07/7/2025

Farida B.

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Italy

I 10 giorni in barca a vela sono stati bellissimi. Un’esperienza che mi ha riempito gli occhi e il cuore… non sarebbe stata tale se non avessi veleggiato in compagnia di bellissime persone con le quali si é creata una piacevole connessione. Ringrazio il “Super Skipper Andrea”, un professionista: competente, affidabile e generoso. Una vacanza che consiglio a chi ama il mare e la libertà!
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From Kalymnos to Samos Dodecanese North on a magnificent 15-meter boat

07/7/2025

Maddalena D.

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Italy

Una settimana bellissima, rigenerante e super positiva. Fabio e Irene ci hanno accolto su Àlisè e ci hanno fatto subito sentire a casa. La barca è bellissima, accogliente e spaziosa. Fabio è un ottimo skipper, molto disponibile e affidabile, mi sono sempre sentita al sicuro nonostante il maltemi non ci abbia mai mollato e a tratti è stato impegnativo. Irene è stata un’ottima co-skipper sia durante la navigazione che nella gestione dei pasti e della cambusa. Anche lei molto disponibile e attenta. Ottima esperienza. Grazie ancora
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Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

07/7/2025

Virginia B.

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Italy

Vacanza bellissima, Andrea skipper preciso e simpaticissimo ci ha fatto scoprire posti meravigliosi e ci ha intrattenuti. Altra menzione d’onore a Marta che ci ha cibati e coccolati. Mattias vero lupo di mare! Mancate giá!

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