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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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4.4

Kos, Kalymnos, Patmos, Leros: sea, colors and jewels of the past

Greece: Dodecanese

6 days - 7 nights

One departure available

June

€650

Per person

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4.8

SHARE & SAIL - 5 days Exploring & Relaxing at the heart of Cyclades

Greece: Cyclades

5 days - 5 nights

3 departures available

May - October

€880

Per person

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5.0

Ionian Islands by Sailing: Trekking, Snorkeling and Sea Adventure

Greece: Ionian Islands

6 days - 6 nights

3 departures available

January - December

€500

Per person

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4.8

SHARE & SAIL - 6 days Exploring & Relaxing at the heart of Cyclades

Greece: Cyclades

6 days - 6 nights

2 departures available

April - May

€990

Per person

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4.4

Preveza, Antipaxos, Paxos and Corfu: between extraordinary landscapes and sea

Greece: Ionian Islands

6 days - 7 nights

One departure available

August

€690

Per person

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4.3

Gone with the Wind, Corfu and the Poseidon Islands

Greece: Ionian Islands

6 days - 7 nights

3 departures available

September

€630

Per person

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4.4

Fairytale scenery in the cradle of Greek culture: from Chios to Limnos

Greece: North Egean Islands

6 days - 7 nights

One departure available

June - July

€660

Per person

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4.4

Discovering the Dodecanese: Rhodes, Symi, Knidos & Kos

Greece: Dodecanese

6 days - 7 nights

One departure available

June

€650

Per person

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4.4

From Greece to Italy, sailing between Corfu, Santa Maria di Leuca, Gallipoli and Crotone

Greece: Ionian Islands

6 days - 7 nights

One departure available

August

€660

Per person

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4.9

Lefkada - Athens: from the green of the Ionian Islands to the adrenaline of the Aegean

Greece: Peloponnese

9 days - 8 nights

One departure available

May

€570

€513

Per person

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4.3

In the Sea of Ulysses among the most beautiful islands on Bavaria 50 with hostess

Greece: Ionian Islands

6 days - 7 nights

8 departures available

July - August

Starting from

€750

€638

Per person

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4.4

From Limnos to the wonderful Sporades: where greenery plunges into the sea

Greece: Sporades

6 days - 7 nights

One departure available

July

€660

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

1905 reviews

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Sailing in the Saronic Archipelago

10/26/2025

Lorenzo Z.

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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.

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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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