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Yacht sailing holidays & skippered tours in Greece

Discover more than 58 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

Starting from

€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

1772 reviews

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

07/6/2025

Dario B.

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Italy

una gran bella esperienza! non è stata la mia prima crociera in barca a vela ma sicuramente la più bella. Alessandro è giovane ma competente, conosce benissimo le zona e i fondali e, cosa non da poco, è gentile e disponibilissimo con tutti. Carlo è formidabile, disponibile, super sportivo e cucina benissimo! insieme al fratello abbiamo creato una piccola flottiglia di due imbarcazioni, e anche un bel gruppo. Con loro abbiamo visto i posti più belli della zona. ero un po’ scettico su Corfù prima di partire, ma mi sono dovuto ricredere, e dalla barca è tutta un’altra prospettiva . 5 stelle su tutto, super meritate.
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

07/6/2025

francesco f.

Che dire.. primo viaggio in barca assolutamente indimenticabile. Grazie ad Ale, lo skipper, sempre attento e disponibile a ogno nostra esigenza o richiesta.. Grazie a Carlo, imprescindibile steward sempre con il sorriso sulle labbra , nonche' ottimo cuoco e grande "suppista". E grazie a entrambi per le chiacchierate piacevoli durante la navigazione. Esperienza che ripeteremo sicuramente con lo stesso equipaggio. Non se, ma quando.. Un saluto anche ad Eros una compagnia breve ma intensa. A presto!.
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

07/6/2025

Claudio S.

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Italy

Settimana bellissima. Destinazioni scelte con cura. L’equipaggio ci ha fatti sentire fin da subito benvenuti. Un grazie speciale ad Alessandro e Carlo che hanno sempre avuto un sorriso per noi e sono sempre stati attenti alle nostre esigenze compatibilmente con la vita da barca. Esperienza da consigliare. Ripeteremo con lo stesso equipaggio il prima possibile.
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From Sicily to Greece crossing the Strait of Messina

07/6/2025

Barbara B.

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Hungary

Skipper is not speaking English at all, however he marked language knowledge on his profile . The communication issues made strange situations on the boat. Boat wasn't 100% clean when we were onboarded and we were also not allowed to use the inside showers on the boat (we had no stops in Ports with shower opportunities during the cruise )

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