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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!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

3 departures available

September - October

Starting from

€550

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

4 departures available

September - November

Starting from

€650

€618

Per person

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5.0

Super!

The enchantment of the sea: the Dodecanese islands

Greece: Dodecanese

7 days - 7 nights

One departure available

September

€750

Per person

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5.0

Super!

Sailing in the eastern Aegean, between the Dodecanese and the Cyclades!

Greece: Dodecanese

8 days - 8 nights

One departure available

September

€650

Per person

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4.8

Super!

Milos, Kimolos, Poliegos, Folegandros, the fantastic Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€870

Per person

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4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

One departure available

September

€955

€790

Per person

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4.9

Super!

Fast cruising Cicladi Occidentali

Greece: Cyclades

6 days - 7 nights

One departure available

August - September

€955

€790

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

3 departures available

September - October

€750

Per person

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4.9

Super!

Mykonos to Athens by Fast Cruise

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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4.8

Super!

Paros, Serifos, Kytnos, the fantastic Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€790

€711

Per person

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4.8

Super!

Milos to Paros: the best of the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

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

8 departures available

August - October

Starting from

€1,100

€1,045

Per person

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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

1845 reviews

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Sailing cruise in the Greek islands - The Saronic Islands

08/27/2025

RENATO G.

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Italy

With Bertrand, Laura, Marta and Jillian it was a beautiful experience, rich from a human and naturalistic point of view. Bertrand is a professional skipper, attentive to safety and available and flexible to our needs. We customized the tour according to our indications and taking care to check the weather conditions. This is our tour: DAY 1 AEGINA EPIDAURUS Taverna Perivoli Tis Gogos DAY 2 Geronimali Beach (Paros) POROS Apagio Restaurant DAY 3 HYDRA Restaurant Kodylenias Paralia Kaminia (beach) Restaurant Xelia Delia Douskos Amalour Lemon Tree DAY 4 HYDRA SPETSES Paralia Zogerias (beach) KORAKIA DAY 5 KORAKIA HERMIONI Cavos Taverna DAY 6 HERMIONI Cape Skyli South POROS Vagionia Beach DAY 7 POROS Vagionia Beach Nisis Metopi South (Nisis/Isoletta) Nisis Moni AGKISTRI / Skilomango West DAY 8 AEGINA Renvi (Restaurant) We sailed, motored and spent beautiful and carefree days in contact with nature, the sea (splendid), between ports and coves. Bertrand is an excellent connoisseur of these places, restaurants, bars.... We followed his advice and had a great time. It was our human TripAdvisor. We had some nice barbecues on the boat and learned something about life on the boat every day. I enjoyed helping out in various activities necessary for the management of the boat. Our group was very close-knit and we always did everything together touring the islands. No problems of any kind. The galley costs were in line with expectations. We spent a nice evening together at HYDRA on August 15th. There was no shortage of experiences at sea, in the water, sightings of fish, dolphins, birds. Even though the period was very busy, Bertrand and I always managed to find good solutions and avoid stress. The boat has some details to maintain but overall it was comfortable and we didn't miss anything. Thanks to Bertrand, Bla Bla Girlz and Champagne Girl for this experience that will remain among my and Laura's good memories. Highly recommended experience and for us it is a goodbye!
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Fast cruising Cicladi Occidentali

08/26/2025

Sergio B.

-

Italy

Annalisa and Lorenzo are first and foremost two wonderful people. Then they are two very experienced sailors: they have sailed around the world; they know the waters of the Aegean by heart. Finally, they are also great as cooks: where do you find the barbecue on the boat and the freshly hand-pulled egg pasta below deck? Only from them! The bays where they took us were breathtaking.
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Short trip around Paros and the small Cyclades

08/26/2025

Eva A.

-

Italy

Great trip and company!
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Two weeks in flotilla between the Cyclades and the Peloponnese

08/25/2025

GIULIO F.

-

Italy

Extremely positive experience, friendly atmosphere and family atmosphere. Destinations chosen with care and beyond expectations. Tested and functional organization for the success of the trip. 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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