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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!

130

experiences

130

experiences

A week to discover the Cyclades Islands by Catamaran

Duration:

6 days - 7 nights

Greece:

Cyclades

Give this experience a try!

€1,000

Per person

5.0

I mari di Ulisse: da Lefkas a Zante

Duration:

6 days - 7 nights

Greece:

Ionian Islands

+6 travellers

have booked

€490

Per person

4.9

Cyclades and Microcyclades with a magnificent 15-meter boat

Duration:

6 days - 7 nights

Greece:

Cyclades

+6 travellers

have booked

Starting from

€590

Per person

4.6

Tour del Peloponneso e isole Ioniche su una barca di 17 metri con Chef

Duration:

9 days - 9 nights

Greece:

Peloponnese

+3 travellers

have booked

€980

Per person

5.0

Discovering the Southern Dodecanese

Duration:

6 days - 7 nights

Greece:

Dodecanese

Give this experience a try!

€550

Per person

4.7

Big and luxurious 60ft catamaran in Saronic, the best local experience

Duration:

6 days - 7 nights

Greece:

Saronic Islands and Athens area

Give this experience a try!

Starting from

€1,499

Per person

4.9

Crossing from Lefkada to Athens.... Adventure not to be missed!

Duration:

7 days - 8 nights

Greece:

Peloponnese

Give this experience a try!

€430

Per person

5.0

Da Zante a Milos attorno al Peloponneso, un itinerario incontaminato

Duration:

6 days - 7 nights

Greece:

Peloponnese

+5 travellers

have booked

€395

Per person

5.0

What a treat to sail between Rhodes and Kos, en-suite cabins

Duration:

6 days - 7 nights

Greece:

Dodecanese

Give this experience a try!

€598

€650

Per person

Sailing weekend in Greece - Diapontie islands

Duration:

3 days - 3 nights

Greece:

Ionian Islands

Give this experience a try!

€300

Per person

5.0

Explore the charms of Greece aboard our sailboat

Duration:

6 days - 6 nights

Greece:

Ionian Islands

Give this experience a try!

€700

Per person

5.0

100% women's sailing cruise

Duration:

6 days - 7 nights

Greece:

Cyclades

+9 travellers

have booked

€860

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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