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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!

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5.0

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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

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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!

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

Greece: Cyclades

7 days - 7 nights

One departure available

August

€990

Per person

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5.0

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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

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

September

€955

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

August

€1,000

Per person

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4.9

Super!

From Paros to Mykonos

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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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

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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

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4.9

Super!

Mykonos to Athens by Fast Cruise

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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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

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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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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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Guides & tips


Greece

Ionian Islands, Cyclades Islands and Dodecanese are just some of the most beautiful destinations for a sailing or catamaran vacation in Greece
Guide to Greece by sailboat

Ionian Islands

Paxos, Zakynthos, Kefalonia and Lefkada are just some of the best destinations for a sailing or catamaran vacation in the Ionian Islands.
Guide to Ionian Islands by sailboat

Cyclades islands

Sandy beaches, small bays and blue and white villages have made the Cyclades a world-famous landscape, perfect for exploring by sailboat or catamaran.
Guide to Cyclades islands by sailboat

Greece: the most beautiful places to sail

Greece: departures by month

Other travel ideas

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