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2035144220

Yacht sailing holidays & skippered tours in Greece

The Greek Archipelago has over 16,000 km of coastline, with many beaches that run for kilometres, a host of secluded bays and coves, and a rich variety of wildlife. Some say the best sailing waters in the world can be found in Greece!

100

experiences

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

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

4.9

Super!

Astypalaia, Anafi and Santorini: the pearls of the Southern Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August

€990

Per person

5.0

Super!

Seven days in the blue on the trail of Ulysses

Greece: Ionian Islands

7 days - 7 nights

One departure available

August

€1,000

Per person

4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

September

€955

Per person

5.0

Super!

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

Greece: Dodecanese

7 days - 6 nights

One departure available

August

€1,000

Per person

4.9

Super!

From Paros to Mykonos

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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

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

4.9

Super!

Mykonos to Athens by Fast Cruise

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

4.9

Super!

From Rhodes to Kos: the fantastic South Dodecanese

Greece: Dodecanese

7 days - 7 nights

One departure available

July

€880

€836

Per person

5.0

Super!

Seven days in the blue on the trail of Ulysses

Greece: Ionian Islands

7 days - 7 nights

One departure available

August

€1,000

Per person

Why book a holiday with Sailsquare?

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80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

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Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

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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

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

07/7/2025

Diana U.

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! :)

From the Dodecanese to the Cyclades: sailing off the beaten track!

07/7/2025

Farida B.

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!

From Kalymnos to Samos Dodecanese North on a magnificent 15-meter boat

07/7/2025

Maddalena D.

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

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

07/7/2025

Virginia B.

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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