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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

7 islands in VIP formula - only 4 guests on board

Greece: Dodecanese

8 days - 8 nights

5 departures available

July - August

€1,350

€1,282

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

11 departures available

June - November

Starting from

€650

€618

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

3 departures available

July - August

Starting from

€2,737

€2,600

Per person

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4.3

Premium

ATHENS Dream Premium - All Inclusive Catamaran Cruise with Stewardess

Greece: Saronic Islands and Athens area

7 days - 7 nights

19 departures available

June - October

Starting from

€1,260

Per person - min 2 pax

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Autumn Gems of Cyclades away from the crowds on 51 ft yacht

Greece: Cyclades

7 days - 7 nights

One departure available

October

€580

Per person

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4.9

From Kalymnos to Samos Dodecanese North on a magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

3 departures available

June - August

Starting from

€800

Per person - min 2 pax

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4.9

Kalymnos Paros via Astipalea e Santorini

Greece: Cyclades

7 days - 7 nights

One departure available

September

€750

Per person - min 2 pax

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3.2

2 Catamarans in Greece: discover the Sporades Islands with us

Greece: Sporades

11 days - 11 nights

One departure available

August

€2,226

Per person

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4.8

Magical Week of Wellness Yoga, Cooking, Health, and Relaxation

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€1,200

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

2 departures available

June - August

Starting from

€800

Per person

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4.6

From Kos to Rhodes on my catamaran

Greece: Dodecanese

7 days - 7 nights

One departure available

August - September

€980

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

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.

-

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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