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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

Super!

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

Greece: Dodecanese

7 days - 6 nights

One departure available

May

€800

€560

Per person

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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

2 departures available

May - August

Starting from

€950

€665

Per person

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Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

4 departures available

May - October

Starting from

€997

€798

Per person

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Sailing & Diving in the Small Cyclades

Greece: Cyclades

7 days - 7 nights

3 departures available

July - September

Starting from

€1,020

€816

Per person

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5.0

Super!

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

Greece: Dodecanese

7 days - 6 nights

2 departures available

July - September

Starting from

€1,050

€840

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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5.0

Super!

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

Greece: Cyclades

7 days - 6 nights

One departure available

June

€1,050

€840

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

12 departures available

May - October

Starting from

€585

€497

Per person

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From Paros to Milos, the hidden gems of Cyclades

Greece: Cyclades

5 days - 5 nights

3 departures available

June - September

Starting from

€900

€765

Per person

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Paros-Naxos and Small Cyclades

Greece: Cyclades

5 days - 5 nights

2 departures available

June - September

Starting from

€900

€765

Per person

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4.9

Super!

Fast sailing holiday in the Cyclades with gourmet cuisine on board

Greece: Cyclades

6 days - 7 nights

One departure available

June

€890

€780

Per person

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Sailing the Small Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

July - October

€876

€788

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

1740 reviews

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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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Sailing cruise in the Greek islands - The Saronic Islands

05/4/2025

Riccardo P.

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Italy

La barca è curata ed in ottime condizioni. Bertrand è premuroso, affidabile e sempre disponibile. Le isole Saroniche sono state una bellissima scoperta e meritano sicuramente di essere visitate. Una settimana fantastica!
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Pack your suitcase and we'll take care of the rest!! Stewards on board!

04/21/2025

Luna G.

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Belgium

We just had an amazing holiday! Alessandro and his brother Andrea made sure everything was perfect and truly unforgettable. Everything was well-organized and taken care of down to the smallest detail. They constantly checked if we needed anything and made us feel completely at ease. The food on board was absolutely delicious every single time. Thanks to them, it really felt like a dream vacation. Highly recommended!

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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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