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2035144220

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!

experiences

A week from Kefalonia to Zakynthos, Ithaca and neighboring islands.

Greece: Ionian Islands

7 days - 7 nights

One departure available

August

€700

Per person

4.9

Kalymnos Rhodes Dodecanese South on magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€1,100

Per person - min 2 pax

4.7

Premium

One way Naxos - Aegina sailing adventure on a big 50ft sailboat

Greece: Cyclades

6 days - 7 nights

One departure available

August

€1,050

Per person

5.0

Seven days in the blue on the trail of Ulysses

Greece: Ionian Islands

7 days - 7 nights

One departure available

August

€1,000

Per person

4.3

In the Sea of Ulysses among the most beautiful islands

Greece: Ionian Islands

6 days - 7 nights

6 departures available

July - August

Starting from

€860

€774

Per person

4.5

CYCLADIC ESCAPE - Active Holidays: 5 days Sailing & Exploring Unknown Greece

Greece: Cyclades

4 days - 4 nights

3 departures available

October

€790

Per person

5.0

Explore Peloponnese by sailboat (18 - 40 years old)

Greece: Peloponnese

7 days - 7 nights

14 departures available

July - October

Starting from

€795

Per person

4.3

Premium

ATHENS Dream Premium - All Inclusive Catamaran Cruise with Stewardess

Greece: Saronic Islands and Athens area

7 days - 7 nights

10 departures available

July - October

Starting from

€1,260

Per person - min 2 pax

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

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

September - October

Starting from

€997

€798

Per person

4.9

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

Greece: Dodecanese

7 days - 7 nights

2 departures available

July - August

Starting from

€1,000

Per person - min 2 pax

4.7

Premium

Big and luxurious 60ft catamaran in Saronic - best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

3 departures available

October

€2,100

€1,995

Per person

Why book a holiday with Sailsquare?

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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

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

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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

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

1777 reviews

Experience the sea at 360 degrees? embark with us in Kos

07/9/2025

Davide M.

Italy

Undecided about the choice of holiday to face, Gianfranco immediately put me at ease, so much so that it was difficult to get off his "[hidden]" on the last day. Crazy holiday with swimming in spectacular pristine coves not to mention the excellent restaurants he recommended. Gianfranco find me a location where you can dance Boogie boogie for June 2026 . Thanks again and we will see you again soon

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

07/7/2025

Diana U.

Italy

Amazing experience! It was my first time on a sailing boat, and it was incredible. We visited beautiful places and beaches. Ale and Carlo are the perfect duo to sail with! Ale is professional, knows everything about sailing and the best beaches, and was always available and super friendly. Carlo was also very kind and helpful. I'm a vegetarian, and he always made something special just for me. Thank you for an unforgettable week! Hope to come back soon! :)

From the Dodecanese to the Cyclades: sailing off the beaten track!

07/7/2025

Farida B.

Italy

The 10 days on a sailing boat were beautiful. An experience that filled my eyes and heart... it would not have been such if I had not sailed in the company of beautiful people with whom a pleasant connection was created. I thank the "Super Skipper Andrea", a professional: competent, reliable and generous. A holiday that I recommend to those who love the sea and freedom!

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

07/7/2025

Maddalena D.

Italy

A beautiful, regenerating and super positive week. Fabio and Irene welcomed us on Àlisè and immediately made us feel at home. The boat is beautiful, cozy and spacious. Fabio is an excellent skipper, very helpful and reliable, I always felt safe despite the fact that the maltemi never gave up on us and at times it was challenging. Irene was a great co-skipper both during the navigation and in the management of meals and the galley. She was also very helpful and attentive. Great experience. Thanks again

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