experiences

4.9

Super!

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

Greece: Ionian Islands

7 days - 7 nights

2 departures available

July - August

Starting from

€550

Per person

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

July - August

Starting from

€550

Per person

4.9

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

July - August

Starting from

€650

€618

Per person

5.0

Super!

Corfu and the Ionian Islands

Greece: Ionian Islands

6 days - 7 nights

2 departures available

July

€790

Per person

4.8

Super!

Come and discover the Saronic Islands from Poros

Greece: Saronic Islands and Athens area

6 days - 6 nights

2 departures available

July

Starting from

€585

€497

Per person

4.8

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

July - August

Starting from

€600

€540

Per person

4.9

Super!

From Kos to Rhodes: the beautiful south Dodecanese

Greece: Dodecanese

7 days - 7 nights

One departure available

July

€800

Per person

4.9

Super!

From Rhodes to Kos: the fantastic South Dodecanese

Greece: Dodecanese

7 days - 7 nights

One departure available

July

€880

€836

Per person

5.0

Super!

Experience the sea at 360 degrees? embark with us in Kos

Greece: Dodecanese

7 days - 6 nights

One departure available

July

Starting from

€850

€750

Per person

4.7

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

One departure available

July

Starting from

€1,100

€1,045

Per person

3.7

Adventure around Lefkada, Khefalonia, Ithaca and Zakynthos

Greece: Ionian Islands

6 days - 6 nights

3 departures available

July - August

Starting from

€500

Per person

5.0

7 islands in VIP formula - only 4 guests on board

Greece: Dodecanese

8 days - 8 nights

One departure available

July

€1,350

Per person

Why book a holiday with Sailsquare?

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

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

1768 reviews

Big and luxurious 60ft catamaran in Saronic - best local experience

07/5/2025

Gill B.

United Kingdom

One of our best holidays ever! Beautifully kept boat, beautiful food, beautiful people to be with for a week… would definitely book again !

From Rhodes to Kos: the fantastic South Dodecanese

07/1/2025

Patrizia F.

Italy

Andare in barca con Alessio e Anna è stata una delizia , baie splendide , Alessio sempre molto attento a capire i posti dove fermarsi e come accontentare tutti nei limiti del possibile. Anna deliziosa e preziosa con la sua instancabile energia. Consiglio di provare !

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

06/30/2025

Gilberto B.

Italy

Alessandro, Carlo, Andrea e Marta sono andati oltre ogni possibile aspettativa regalandoci una settimane di relax, incantevoli spot nello ionico, deliziosi pranzi a bordo e fuori. Abbiamo trovato disponibilità, sensibilità e accoglienza fuori dal comune. Barca pulita, ottima comunicazione e organizzazione. Nessun dettaglio lasciato al caso, una vacanza indimenticabile!

From Rhodes to Kos: the fantastic South Dodecanese

06/30/2025

Silvia A.

Italy

Bellissima esperienza oltre ogni aspettativa. Lo skipper super disponibile e simpatico e i luoghi visitati di una bellezza autentica hanno reso questa vacanza ,insieme alle altre persone che erano con me , davvero indimenticabile ❤️ Grazie di cuore

Customer Support

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!

Call us at

+44 2035144220

Read our

Contact & Support

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!