header cover
sailsquare logo

Yacht sailing holidays & skippered tours in Greece

Discover more than 18 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

cover image
avatar image

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

October - November

Starting from

€550

Per person

cover image
avatar image

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

3 departures available

October

Starting from

€1,100

€880

Per person

cover image
avatar image

4.8

Super!

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

Starting from

€2,100

€1,995

Per person

cover image
avatar image

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

cover image
avatar image

5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

One departure available

October

€550

Per person

cover image
avatar image

5.0

Super!

Secret Aegean with skipper and kitchen on board - Rhodes to Kos

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

cover image
avatar image

5.0

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

September - October

€1,080

Per person

cover image
avatar image

5.0

Super!

Secret Aegean with skipper and kitchen on board - Karpathos to Rhodes

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

cover image
avatar image
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

cover image
avatar image

4.5

CYCLADIC ESCAPE - Active Holidays: 5 days Sailing & Exploring Unknown Greece  

Greece: Cyclades

4 days - 4 nights

One departure available

October

€790

Per person

cover image
avatar image

4.3

Premium

ATHENS Dream Premium - All Inclusive Catamaran Cruise with Stewardess

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

October

Starting from

€1,260

Per person - min 2 pax

cover image
avatar image

4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

October

€897

€807

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

1884 reviews

avatar image

From Samos to North Dodecanese Kalymnos on a magnificent 15-meter boat

09/16/2025

Bruno P.

We had a great time aboard the Alizé! As the other passengers have already indicated, Fabio and Irene, thanks to their professionalism, their kindness, their attention to detail and also (this is important! :)) their delicious dishes, allowed us to enjoy a week of happy disconnection. They quickly understood what we liked (fishing, sailing, hiking and discovering the beautiful Greek islands) and adapted the program accordingly. For us, we didn't spend a week with two strangers, but with friends. See you next year!
avatar placeholder

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

09/15/2025

Florian H.

-

Germany

Great trip & great skipper!
avatar placeholder

Gone with the Wind, Corfu and the Poseidon Islands

09/15/2025

Annamaria S.

-

Italy

Nice holiday in the blue of the sky and the sea!! On the other hand, the return to the gray sky and traffic of Bergamo was challenging
avatar image

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

09/15/2025

Claudio S.

-

Italy

Unforgettable trip! Skipper and hostess were super skilled, kind and always available. Great food, stunning places, the magic of sailing and the best company on board. Couldn’t ask for more!

Customer Support

nightLifeGeneralInfo

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

search

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964