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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!

128

experiences

128

experiences

Wandering around the Ionian Islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

Give this experience a try!

€900

Per person

Salt, Earth and Sun: yoga retreat on a catamaran with hostess (Full Board)

Duration:

7 days - 7 nights

Greece:

North Egean Islands

Starting from

€1,855

Per person

4.9

A week exploring the Dodecanese

Duration:

6 days - 7 nights

Greece:

Dodecanese

+8 travellers

have booked

Starting from

€870

Per person

4.6

A real sailing trip, archaeological sites and beaches between Zakynthos and Athens

Duration:

6 days - 7 nights

Greece:

Peloponnese

Give this experience a try!

€750

Per person

4.7

Wandering through the Ionian Islands

Duration:

6 days - 7 nights

Greece:

Ionian Islands

+11 travellers

have booked

€800

Per person

5.0

Cyclades Islands Sailing - oneway Athens (Lavrio) - Mykonos

Duration:

6 days - 7 nights

Greece:

Cyclades

Francesca

has booked

€850

Per person

4.8

In the sea of Ulysses among the most beautiful islands - two boats together

Duration:

6 days - 7 nights

Greece:

Ionian Islands

+2 travellers

have booked

Starting from

€750

Per person

4.9

Athens to Lefkada via the Corinth Canal - Stewardess on board

Duration:

7 days - 7 nights

Greece:

Saronic Islands and Athens area

Giancarlo

has booked

€745

Per person

Climbing to the north - Aegean sea

Duration:

8 days - 7 nights

Greece:

Sporades

Give this experience a try!

€950

Per person

5.0

SECRET DODECANESE: Astypalea and Tylos with skipper and kitchen

Duration:

6 days - 6 nights

Greece:

Dodecanese

+4 travellers

have booked

Starting from

€750

Per person

Enjoy the Greek islands and the blue of Ionian sea, the daily gentle breeze wind of ionian islands

Duration:

7 days - 7 nights

Greece:

Ionian Islands

Give this experience a try!

€788

€840

Per person

5.0

Cyclades and Small Cyclades

Duration:

6 days - 7 nights

Greece:

Cyclades

+4 travellers

have booked

Starting from

€950

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.

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

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

1543 reviews

Sailing Cyclades

04/15/2024

yannis b.

France

Séjour incroyable avec Yann ! Très attentif, drôle et chill dans toutes les situations, dans un bateau très confortable !

Sailing course in the Cyclades

10/18/2023

Antoine B.

Belgium

Superbe semaine avec Sylvain. Skipper professionnelle qui vous mets a l'aise et vous explique tout. Il vous emmène a des magnifiques mouillages et nous avons descendu les petites cyclades rapidement. Le bateau est très confortable et très chouette a naviguer même quand le vent est au dessus des 30 nœuds. Je vous recommandes Sylvain pour votre prochaine aventure!

SHARE & SAIL: explore Cyclades with new friends

10/10/2023

Monica F.

Australia

We had the absolute best time on our trip and would 100% recommend this to anyone looking to explore the Greek Islands. Orestis was the best skipper, very attentive and knowledgeable and willing to join in on the fun. We had a great crew who were up for the adventure and really loved the sailing aspect along with all the challenges that come with it. If you’re looking for a hands on, real down to earth experience then this would definitely be for you. This trip was the highlight of our time in Greece! Thank you Orestis and George :)

Best local experience and amazing views in Cyclades on a big 50 ft boat

10/8/2023

Umberto B.

Italy

La gestione della vacanza è stata come indicato nel programma. La barca Zorbas è molto comoda anche per me che sono alto 1.90 e che potevo stare comodamente in piedi nella Dinette e nell’ingresso alla cabina. Abbiamo fatto delle belle navigate a vela partecipando attivamente al cambio vele e agli ormeggi. Le colazioni e i pranzi preparati da Aga erano sempre perfetti. Abbiamo anche fatto una Avventurosa discesa ad una Taverna tipica in una isola disabitata. Compagni di crociera a dir poco fantastici! Insomma…Vacanza molto piacevole e rilassante!

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