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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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Discovering the Dodecanese from KOS

Greece: Dodecanese

7 days - 7 nights

One departure available

June

€1,300

Per person

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5.0

Corfù Paxos Antipaxos

Greece: Ionian Islands

6 days - 6 nights

4 departures available

June - September

Starting from

€900

Per person

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4.6

The Cyclades with Serifos and Mykonos on a dream boat with chef

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,400

Per person

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4.8

Catamarano con Chef nel magico mare delle Isole Ioniche

Greece: Ionian Islands

7 days - 7 nights

6 departures available

June - September

Starting from

€1,150

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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4.7

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

13 departures available

May - October

Starting from

€1,000

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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4.3

By Catamaran between the islands of Poseidon and Corfu

Greece: Ionian Islands

6 days - 7 nights

One departure available

June

€1,080

Per person

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Sail & Yoga Retreat: relaxing catamaran cruise with full board

Greece: Saronic Islands and Athens area

6 days - 7 nights

One departure available

July

Starting from

€2,400

Per person

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SAILING & IDLENESS Argo-Saronic Gulf

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

August - September

€1,960

Per person

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4.6

Among the Dodecanese islands on my catamaran.

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€980

Per person

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5.0

Super!

The enchantment of the sea: the Dodecanese islands

Greece: Dodecanese

7 days - 7 nights

One departure available

September

€650

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

1743 reviews

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Sailing cruise in the Greek islands - The Saronic Islands

05/28/2025

Sean M.

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United States

Bertrand is a true sailor! We had a great time sailing between quiet anchorages and lively villages around the Saronic islands. Amazing trip
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Sailing cruise in the Greek islands - The Saronic Islands

05/26/2025

Jane V.

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Canada

We had the most amazing week of sailing in the Saronic Islands under the expert guidance of our skipper Bertrand. He encouraged us all to help with the sailing activities, brought us to postcard card perfect locations for swimming, snorkelling, paddle boarding and hiking. We were treated like old friends in every port and taverna due to the good relations Bernard has built with the locals. .The other three guests in the boat were wonderful human beings and made for great company on the week long adventure! It was truly an unforgettable trip and I cannot recommend it enough!! Jane 🇨🇦
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

05/18/2025

Emma K.

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Germany

Ich hatte eine sehr schöne Zeit. Alessandro und Carolina waren sehr nett und haben uns trotz ein paar Tagen Regen gut versorgt. Und sie haben die Route spontan an die Wetterlage angepasst. Einfach top Erfahrung. Danke!
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Sailing cruise in the Greek islands - The Saronic Islands

05/12/2025

Monika L.

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Germany

Skipper Bertrand machte einen super Job! Wir sind unerfahrene Segler und fühlten uns absolut sicher und sehr gut aufgehoben. Auf die mehrtägige Flaute (und seine sehr unterschiedlichen Gäste an Bord) hat Bertrand total flexibel und entspannt reagiert. Mach bitte weiter so! Auch die Orga mit sailsquare war perfekt- wir sind glücklich und sehr zufrieden von Bord gegangen und empfehlen Euch gern weiter!

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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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