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Sailboat yacht sailing holidays & tours in Greece

Discover more than 32 opportunities to get on board a Sailboat adventure in Greece. A unique experience with a local skipper, starting at €350 a week.

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4.8

Super!

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

5 departures available

September - October

Starting from

€1,300

€1,040

Per person

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5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

4 departures available

October

€570

Per person

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4.8

Super!

Cast off for a week at sea, a thousand ways to experience it!

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

September - November

Starting from

€585

€527

Per person

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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

4 departures available

September - October

Starting from

€570

Per person

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4.7

Super!

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

2 departures available

September - October

€600

€540

Per person

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5.0

Super!

Saronic Islands and surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

September

€620

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

2 departures available

October

€750

Per person

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4.8

Super!

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€650

Per person

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4.9

Super!

Cyclades from Milos to Milos

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person - min 2 pax

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5.0

Super!

The Saronic Islands sailing, skippered and on-board kitchen

Greece: Saronic Islands and Athens area

6 days - 6 nights

2 departures available

October

€950

Per person

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5.0

Super!

From Mykonos to Athens by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

€760

Per person

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5.0

Super!

From Milos to Mykonos by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September

€1,000

€750

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 - Sailboat yacht sailing holidays & tours in Greece

1952 reviews

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Sporades Experience: Freedom, Turquoise Sea and Greek Magic

09/8/2026

Cecile G.

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GB

Fantastic experience and week of sailing!

Sporades Experience: Freedom, Turquoise Sea and Greek Magic

09/7/2026

Salvatore Giuseppe Antonio S.

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IT

Beautiful holiday with Gianfranco captain skipper always available and company for a wonderful tour of the islands in the name of relaxation, snorkeling and fun. Recommended for everyone
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Ionian Escape – Sailing Week from Corfu – Paxos & Antipaxos

09/7/2026

Mita M.

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DE

Let's go in order: -the port of departure and arrival is one of the most beautiful I have ever seen, -the boat is very clean and spacious -Roberto is an experienced skipper and company. One evening he entertained us with the guitar. I spent a wonderful week, in excellent company. In addition, the areas visited are very beautiful. Highly recommend
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Sporades Experience: Freedom, Turquoise Sea and Greek Magic

09/7/2026

Max B.

Great trip!

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