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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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4.9

Super!

Lesvos, Oinoussa and Chios on a magnificent 15-meter boat

Greece: North Egean Islands

7 days - 7 nights

One departure available

June

€800

Per person - min 2 pax

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4.8

Super!

Ios, Sikinos, Folegandros and Anafi: the fantastic Cyclades of the South

Greece: Cyclades

7 days - 7 nights

2 departures available

August

€990

€891

Per person

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4.8

Super!

Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays

Greece: Ionian Islands

7 days - 7 nights

10 departures available

May - July

Starting from

€650

€585

Per person

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4.8

Super!

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

22 departures available

May - October

Starting from

€1,100

€990

Per person

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4.8

Super!

The Small Cyclades and spectacular Santorini

Greece: Cyclades

7 days - 7 nights

2 departures available

August - September

Starting from

€940

€846

Per person

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4.8

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

4 departures available

September - October

€750

€713

Per person

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4.9

Super!

Cyclades from Paros to Milos on magnificent 15-meter boat

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person - min 2 pax

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4.9

Super!

Kavala Thassos Samothraki Limnos on a magnificent 15-meter boat

Greece: North Egean Islands

7 days - 7 nights

One departure available

May - June

€800

Per person - min 2 pax

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4.9

Super!

The North Dodecanese from Samos on a magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

2 departures available

June - July

€1,000

Per person - min 2 pax

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4.8

Super!

Paros, Serifos, Kytnos, the fantastic Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August

€950

€855

Per person

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4.9

Super!

From Milos to Zakynthos: the Peloponnese on a magnificent 15-meter boat

Greece: Peloponnese

10 days - 10 nights

One departure available

September

€900

Per person - min 2 pax

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4.8

Super!

Milos to Paros: the best of the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

July - August

€900

Per person

Why book a holiday with Sailsquare?

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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

1905 reviews

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Sailing in the Saronic Archipelago

10/26/2025

Lorenzo Z.

-

Italy

I chose the boat trip precisely to live the experience of sailing. We always sailed by motor, except for a few hours, in the need to dry them after a heavy rain. this even when all the other boats were sailing
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Secret Aegean with skipper and kitchen on board - Rhodes to Kos

10/22/2025

Douglas B.

-

United Kingdom

An extraordinary experience that exceeded all expectations
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Secret Aegean with skipper and kitchen on board - Rhodes to Kos

10/19/2025

Catherine S.

My first sailing experience was simply extraordinary! ⛵️ Unforgettable moments spent at sea, surrounded by incredible people. Anna Lisa and Emmanuel were amazing hosts! Thank you to everyone for your good humor, your kindness and this unique adventure. Can't wait to do it again! 🌊✨
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Secret Aegean with skipper and kitchen on board - Rhodes to Kos

10/19/2025

Olivier P.

-

France

Some sailings leave a softer trace than that of the boat's wake. The sailing week was perfect: beautiful sailing, delicious food and a friendly atmosphere. Thank you to them for this wonderful interlude — I will leave without hesitation!

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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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