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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

Exclusive boat, you choose the route and the Cyclades islands to see!

Greece: Cyclades

7 days - 7 nights

One departure available

September

€917

Per person

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5.0

Southern Greece Pelloponese coast trip

Greece: Peloponnese

7 days - 7 nights

One departure available

September

€490

Per person

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3.0

Sailing the Aegean: a Greek Islands escape - hostess on board (half board)

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

September - October

Starting from

€929

Per person

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New

Corfu: sailing, dream bays and walks in the villages - hostess on board

Greece: Ionian Islands

6 days - 6 nights

9 departures available

August - October

Starting from

€1,200

€500

Per person

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4.7

Greek Islands Catamaran Cruise - Saronic

Greece: Saronic Islands and Athens area

7 days - 7 nights

7 departures available

August - October

Starting from

€820

Per person

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4.4

Gone with the Wind, Corfu and the Poseidon Islands

Greece: Ionian Islands

6 days - 7 nights

2 departures available

September

€630

Per person

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Unique Cyclades sailing holiday with Hostess

Greece: Cyclades

7 days - 7 nights

One departure available

August

€1,249

Per person

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New

Sailing Hidden Greece | Boutique Catamaran Experience

Greece: Saronic Islands and Athens area

6 days - 6 nights

2 departures available

September - October

€1,550

Per person

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New

Premium

All inclusive catamaran cruise on Excess 11 in Ionian Greece with hostess

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August - October

Starting from

€1,875

Per person

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4.2

New

Paros - Athens: temples on the sea and unspoiled blue

Greece: Cyclades

7 days - 7 nights

One departure available

August - September

€990

Per person

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5.0

Exclusive sailing week among the wonders of Ionian Greece

Greece: Ionian Islands

6 days - 7 nights

7 departures available

August - October

Starting from

€1,200

Per person

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4.4

In the Sea of Ulysses among the most beautiful islands

Greece: Ionian Islands

6 days - 7 nights

One departure available

August

€690

Per person

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Get onboard solo, with your family or your friends

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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

2037 reviews

Different flotilla in Ionian Greece: nature, new friends and fun

08/19/2026

Michela B.

-

IT

NEVER AGAIN DIFFERENT SAILING!! Small and dirty boat with smelly and inaccessible bathroom!! Skipper at the first experience and flotilla leader indifferent to the situation!! Lucky to have found a very good coskipper who saved our holiday!! Tourist itinerary!!

Different flotilla in Ionian Greece: nature, new friends and fun

08/18/2026

Flavia U.

-

IT

A journey dedicated to the discovery of enchanting bays, unspoiled nature, new friends and lots of fun.
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Luxury catamaran cruise in the Cyclades

08/18/2026

Paolo F.

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CH

The holiday was made in the Saronics, due to the adverse weather in the Cyclades. It was a good choice since friends later told me that they had had a very bad week because of the wind on those islands. Hydra and Spetses are real gems. Bertrand is very helpful, he accompanied us with the tender even at inconvenient times and always put our safety first. The boat is very comfortable and new, even in 10 you have all the comforts and space you need.

Sailing cruise in the Greek islands - The Saronic Islands

08/18/2026

Catherine B.

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FR

Very enjoyable cruise. Comfortable and well-equipped boat. The islands are all more beautiful than the others and what a joy to wake up alone in the world in a paradisiacal cove! Very good atmosphere thanks to Periklis who knows how to be as efficient as he is discreet and leaves a lot of room for those who want to take part in the navigation. I highly recommend this experience.

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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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