header cover
sailsquare logo

Yacht sailing holidays & skippered tours in Greece

Discover more than 52 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

52

experiences

cover image
avatar image

3.7

Adventure around Lefkada, Khefalonia, Ithaca and Zakynthos

Duration:

6 days - 6 nights

Greece:

Ionian Islands

avatar placeholder
avatar placeholder
avatar placeholder

4 travellers

Starting from

€285

€300

Per person

cover image
avatar image

4.9

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Duration:

7 days - 7 nights

Greece:

Saronic Islands and Athens area

avatar image
avatar image
avatar image

86 travellers

Starting from

€618

€650

Per person

cover image
avatar image

4.4

Premium

ATHENS Dream Premium - All Inclusive Catamaran Cruise with Stewardess

Duration:

7 days - 7 nights

Greece:

Saronic Islands and Athens area

avatar image
avatar placeholder
avatar placeholder

8 travellers

Starting from

€1,260

Per person - min 2 pax

cover image
avatar image

4.9

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

Duration:

7 days - 7 nights

Greece:

Dodecanese

avatar placeholder
avatar placeholder
avatar placeholder

4 travellers

Starting from

€800

Per person - min 2 pax

cover image
avatar image

5.0

Super!

Treat yourself to an unforgettable holiday. Embark with us in Kos

Duration:

7 days - 6 nights

Greece:

Dodecanese

avatar image
avatar placeholder
avatar placeholder

31 travellers

Starting from

€800

Per person

cover image
avatar image

5.0

Corfù Paxos Antipaxos

Duration:

6 days - 6 nights

Greece:

Ionian Islands

avatar placeholder
avatar placeholder
avatar placeholder

12 travellers

Starting from

€900

Per person

cover image
avatar image

4.3

By Catamaran between the islands of Poseidon and Corfu

Duration:

6 days - 7 nights

Greece:

Ionian Islands

Give this experience a try!

Starting from

€750

Per person

cover image
avatar image

5.0

Super!

From the Dodecanese to the Cyclades: sailing off the beaten track!

Duration:

10 days - 10 nights

Greece:

Dodecanese

avatar image
avatar image
avatar image

7 travellers

€800

Per person

cover image
avatar image

4.9

Super!

From Rhodes to Kos: the fantastic South Dodecanese

Duration:

7 days - 7 nights

Greece:

Dodecanese

avatar image
avatar placeholder
avatar placeholder

23 travellers

€800

Per person

cover image
avatar image

4.7

Premium

Sporades one way on a big and comfortable 60ft catamaran with chef

Duration:

5 days - 6 nights

Greece:

Sporades

avatar placeholder
avatar placeholder

2 travellers

€1,998

Per person

cover image
avatar image

5.0

Corfu, Albania and Diapontie Islands

Duration:

6 days - 6 nights

Greece:

Ionian Islands

avatar image
avatar placeholder
avatar placeholder

12 travellers

€900

Per person

cover image
avatar image

4.8

Super!

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

Duration:

7 days - 7 nights

Greece:

Ionian Islands

avatar image
avatar image
avatar image

72 travellers

Starting from

€722

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

1740 reviews

avatar placeholder

Sailing cruise in the Greek islands - The Saronic Islands

05/12/2025

Monika L.

-

Germany

Skipper Bertrand machte einen super Job! Wir sind unerfahrene Segler und fühlten uns absolut sicher und sehr gut aufgehoben. Auf die mehrtägige Flaute (und seine sehr unterschiedlichen Gäste an Bord) hat Bertrand total flexibel und entspannt reagiert. Mach bitte weiter so! Auch die Orga mit sailsquare war perfekt- wir sind glücklich und sehr zufrieden von Bord gegangen und empfehlen Euch gern weiter!
avatar placeholder

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

05/7/2025

Janette G.

-

Australia

After sailing in the teeth of the Meltemi in the eastern Aegean 2 years ago Chris and I were happy to accept an invitation from friends to sail with Sail square in the gentle waters of the southern Corfu strait. Our hopes for a relaxing week on the water were fulfilled, largely due to the sailing skill and the care of Alessandro and his crew. We and our friends were comfortably accommodated in 2 cabins, each with a bathroom. All was clean and well-maintained. Our hostess, Marta, provided delicious Greek breakfasts and lunches. While sailing in the beautiful waters between Corfu, Paxos and Antipaxos, there were many opportunities for swimming at lovely beaches and walking in the islands. Alessandro and his crew, including the ship’s dogs, were exceptionally good hosts and we recommend this experience unreservedly. Lucy and Chris Costas May 2025
avatar placeholder

Sailing cruise in the Greek islands - The Saronic Islands

05/4/2025

Riccardo P.

-

Italy

La barca è curata ed in ottime condizioni. Bertrand è premuroso, affidabile e sempre disponibile. Le isole Saroniche sono state una bellissima scoperta e meritano sicuramente di essere visitate. Una settimana fantastica!
avatar placeholder

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

04/21/2025

Luna G.

-

Belgium

We just had an amazing holiday! Alessandro and his brother Andrea made sure everything was perfect and truly unforgettable. Everything was well-organized and taken care of down to the smallest detail. They constantly checked if we needed anything and made us feel completely at ease. The food on board was absolutely delicious every single time. Thanks to them, it really felt like a dream vacation. Highly recommended!

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

MastercardVisaAmerican ExpressApple pay

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