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Yacht sailing holidays & skippered tours in Greece

Discover more than 28 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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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

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5.0

Explore Peloponnese by sailboat (18 - 40 years old)

Greece: Peloponnese

7 days - 7 nights

3 departures available

October

Starting from

€795

Per person

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4.3

Premium

ATHENS Dream Premium - All Inclusive Catamaran Cruise with Stewardess

Greece: Saronic Islands and Athens area

7 days - 7 nights

2 departures available

October

Starting from

€1,260

Per person - min 2 pax

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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

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Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

October

Starting from

€997

€798

Per person

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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

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Sailing & Diving in the Small Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

October

Starting from

€1,020

€816

Per person

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4.5

DOWNWIND BLAST: One-way Cycladic Adventure Athens to Santorini, 10days

Greece: Cyclades

9 days - 9 nights

One departure available

October

€1,980

Per person

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5.0

Ionian Islands by Sailing: Trekking, Snorkeling and Sea Adventure

Greece: Ionian Islands

6 days - 6 nights

One departure available

October

€750

Per person

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5.0

Sailing to Corfu - (40+ years)

Greece: Ionian Islands

7 days - 7 nights

4 departures available

October - November

Starting from

€732

Per person

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5.0

Explore Peloponnese by sailboat - (40+ years)

Greece: Peloponnese

7 days - 7 nights

3 departures available

October

Starting from

€795

Per person

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4.3

Gone with the wind, discovering the Cyclades

Greece: Cyclades

6 days - 7 nights

5 departures available

September - November

Starting from

€690

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

1788 reviews

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

07/14/2025

Claudia Z.

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Italy

Seven days, one boat, a thousand emotions We spent a wonderful week on a sailing boat exploring the beauties of Corfu and the nearby islands, guided by a skipper who was truly out of the ordinary: Andrea. It is evident that he deeply loves his job – competent, professional, capable of transmitting confidence and serenity even when the weather has decided to throw a tantrum. Two days of forced stop in port could have ruined the spirit of the trip, but Andrea was able to turn everything into an opportunity to discover, learn and relax. Always ready with a kind word, interesting information or a joke at the right time, he did much more than you would expect from a skipper, including top info about the restaurants! Also on board with us was Carlo, a discreet and attentive steward, who with his caring presence made life on board even more comfortable. The boat, spacious and comfortable, was our perfect floating retreat. And Mattias, the poodle on board? A sweet cuddle that conquered everyone, including the most insensitive to hairy faces. An added value was the proximity of the boat of Andrea's brother, Alessandro: this allowed us to get to know the participants of his boat and to share very pleasant moments together, including aperitifs, laughter and chats under the stars. If I really have to find a point on which to suggest an improvement but it is a constructive personal thought: it is the kitchen. With a little more focus on variety, ingredient quality, and presentation, the experience could really level up. Because, let's face it, customers are often won over even with just a well-thought-out dish! That said, it was a holiday full of excitement, beautiful scenery and great company. We would gladly do it again and I will over-recommend it to friends at home – maybe without wind, but always with Andrea at the helm!
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The alternative to the catamaran in the Sporades

07/14/2025

Pietro M.

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Italy

The sailing experience with Manuele was magical. He is a formidable captain, attentive to everything around him, always transmitting confidence and passion in everything he does. An exceptional chef who surprises you every day with his dishes. Being able to share this experience with him was a privilege that I wish for everyone. He made me fall in love with sailing, I will definitely come back with him for more adventures.
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Sailing and Hiking in the Cyclades

07/14/2025

Marco P.

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Italy

We had a very nice holiday!
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The alternative to the catamaran in the Sporades

07/14/2025

Ginevra S.

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Italy

This holiday aboard Mowgli was one of the best experiences of my life. It was the first time I got on a sailboat and initially I was a bit worried about not being able to sleep and not enjoy the holiday. Manuele, however, made me feel at home from the first moment, cooking excellent meals and taking care of each crew member. Manuele thought about the safety of the group at all times, taking us to coves sheltered from the strong Greek winds to ensure us a peaceful sleep and letting us explore wonderful places. Needless to say, once the holiday was over and she got off the boat, I immediately felt a very strong nostalgia! I can't wait to get back on board Mowgli.

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