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

October

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

2 departures available

October

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

October - November

Starting from

€650

€618

Per person

5.0

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

3 departures available

September - October

Starting from

€1,080

Per person

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

4.9

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

€713

Per person

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

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

3 departures available

October

Starting from

€1,100

€1,045

Per person

4.5

SHARE & SAIL - 6 days Exploring & Relaxing at the heart of Cyclades

Greece: Cyclades

6 days - 6 nights

2 departures available

October

€790

Per person

5.0

Sailing holiday with yoga and SUP in the Saronic islands

Greece: Saronic Islands and Athens area

6 days - 7 nights

2 departures available

October

Starting from

€990

Per person

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

October

Starting from

€997

€798

Per person

Sailing the Small Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

October

Starting from

€789

€710

Per person

Why book a holiday with Sailsquare?

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Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

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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

1767 reviews

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

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

06/30/2025

elisabetta m.

Italy

Andrea è un professionista, sempre pronto a renderti felice! Abbiamo visitato posti stupendi e in condizioni di vento e mare piuttosto impegnative, che solo un esperto marinaio poteva rendere cosi' piacevoli!

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