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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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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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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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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

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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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Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

September

€955

Per person

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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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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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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

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5.0

Super!

Secret Aegean with skipper and kitchen on board - Rhodes to Karpathos

Greece: Dodecanese

7 days - 6 nights

One departure available

September - October

€950

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

1780 reviews

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

07/12/2025

Attilio A.

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Italy

Excellent welcome, well-designed itinerary, excellent on-board cuisine.
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South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

07/12/2025

IOANNIS P.

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Greece

Everything was perfect
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Heart of the Cyclades Cruise: Milos to Mykonos

07/12/2025

Annalisa M.

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United Kingdom

A beautiful trip completely met my expectations, Andrea with his professionalism handled all situations excellently.
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Experience the sea at 360 degrees? embark with us in Kos

07/9/2025

Davide M.

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Italy

Undecided about the choice of holiday to face, Gianfranco immediately put me at ease, so much so that it was difficult to get off his "[hidden]" on the last day. Crazy holiday with swimming in spectacular pristine coves not to mention the excellent restaurants he recommended. Gianfranco find me a location where you can dance Boogie boogie for June 2026 . Thanks again and we will see you again soon

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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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