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Yacht sailing holidays & skippered tours in Greece

Discover more than 18 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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5.0

Super!

Secret Aegean with skipper and kitchen on board from Samos to Mykonos

Greece: Sporades

7 days - 6 nights

One departure available

May - June

Starting from

€950

€665

Per person

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3.2

2 catamarans to discover the Central Cyclades and Micro Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

May - June

Starting from

€1,113

€890

Per person

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4.6

From Athens to Evia and Skiathos,: the Sporades on a yacht with chef - One Way

Greece: Sporades

7 days - 7 nights

One departure available

May - June

€1,150

€978

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

2 departures available

May - June

Starting from

€650

€618

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

One departure available

May - June

Starting from

€1,000

Per person

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4.8

Come and discover the Saronic Islands from Poros

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

May - June

Starting from

€500

Per person

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Daily trip around Symi island

Greece: Dodecanese

1 day - 0 nights

3 departures available

May

€125

Per person

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Up and down the Ionian Islands

Greece: Ionian Islands

7 days - 7 nights

One departure available

May - June

€1,200

Per person

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4.9

Cyclades and Microcyclades with a magnificent 15-meter boat

Greece: Cyclades

7 days - 7 nights

One departure available

May - June

€750

Per person

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5.0

Sailing Yoga and SUP trip in the SARONIC ISLANDS Greece

Greece: Saronic Islands and Athens area

6 days - 7 nights

One departure available

May - June

Starting from

€990

Per person

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4.3

Gone with the Wind, Corfu and the Poseidon Islands

Greece: Ionian Islands

6 days - 7 nights

One departure available

May - June

€595

Per person

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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

One departure available

May - June

Starting from

€550

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

1742 reviews

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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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Pack your suitcase and we'll take care of the rest!! Stewards on board!

05/7/2025

Janette G.

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Australia

After sailing in the teeth of the Meltemi in the eastern Aegean 2 years ago Chris and I were happy to accept an invitation from friends to sail with Sail square in the gentle waters of the southern Corfu strait. Our hopes for a relaxing week on the water were fulfilled, largely due to the sailing skill and the care of Alessandro and his crew. We and our friends were comfortably accommodated in 2 cabins, each with a bathroom. All was clean and well-maintained. Our hostess, Marta, provided delicious Greek breakfasts and lunches. While sailing in the beautiful waters between Corfu, Paxos and Antipaxos, there were many opportunities for swimming at lovely beaches and walking in the islands. Alessandro and his crew, including the ship’s dogs, were exceptionally good hosts and we recommend this experience unreservedly. Lucy and Chris Costas May 2025

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