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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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4.9

Super!

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

Greece: Ionian Islands

7 days - 7 nights

12 departures available

June - October

Starting from

€550

Per person

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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

12 departures available

June - October

Starting from

€550

Per person

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4.8

Super!

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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4.9

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

8 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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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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4.7

Premium

Big and luxurious 60ft catamaran in Cyclades - best local experience with hostess

Greece: Cyclades

6 days - 7 nights

2 departures available

August

Starting from

€2,737

€2,600

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board from Santorini to Kos

Greece: Cyclades

7 days - 6 nights

One departure available

June

€1,050

€840

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

8 departures available

June - October

Starting from

€500

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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4.9

Super!

From Kos to Rhodes: the beautiful south Dodecanese

Greece: Dodecanese

7 days - 7 nights

2 departures available

June - July

€800

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

1748 reviews

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

06/11/2025

Gemma M.

-

Italy

Un soggiorno meraviglioso reso speciale da Andrea e Marta, due persone splendide che ci hanno fatti sentire subito a casa. La barca è bellissima, curata e in perfette condizioni. Andrea, skipper esperto e sempre disponibile, ci ha accompagnati con il gommone alla scoperta dei luoghi più belli e nascosti, lasciandoci sempre liberi di scegliere il ritmo della giornata. Marta, cuoca eccezionale, ha preparato piatti deliziosi e ha mantenuto la barca sempre pulita e in ordine con una discrezione e una dedizione davvero ammirabili. La compagnia di Matthias, cane dolce e affettuoso, è stata un piacevole valore aggiunto. Un’esperienza davvero unica.
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Sail from Milos to Mykonos with a Beneteau 50 experience the Cyclades

06/7/2025

Denis P.

-

Italy

Splendida settimana tra le Cicladi… Gianfranco é davvero un grande capitano, che oltre alle doti nautiche sa anche coinvolgerti nella navigazione e farti sentire subito a tuo agio a bordo… La barca poi… Splendida! L’unico problema é il dover sbarcare al termine della vacanza… Grazie Gianfranco!
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Corfu to Athens via the exciting Corinth Canal

06/7/2025

Irene A.

-

Italy

Bellissima esperienza. Enrica e Omar sono due persone esperte di vela e con una grande attenzione agli ospiti. Abbiamo visitato una Grecia inedita e in ogni momento abbiamo condiviso esperienze e bellissime sensazioni. Consiglio a tutti un viaggio con loro per una vacanza dove avventura, comfort e mare si coniugano in modo naturale e divertente. Grazie Enrica e Omar. Sarò sicuramente vostra ospite di nuovo!
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Sail from Milos to Mykonos with a Beneteau 50 experience the Cyclades

06/6/2025

Alessandra C.

-

United States

Esperienza meravigliosa! Gianfranco è uno skipper fantastico, simpatico e dalle mille risorse, ci ha fatto vedere posti bellissimi navigando sempre in sicurezza. La [hidden] è spaziosa e confortevole, una splendida barca! Le Cicladi sono isole meravigliose con acqua cristallina, delfini, tartarughe, cibo delizioso e magici paesini da visitare. Vacanza assolutamente raccomandata!

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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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